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How To Deal With Self-Doubt and Imposter Syndrome

February 3, 2019

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Episode Summary

Let us start off by saying EVERYONE deals with self-doubt. Especially when it comes to running your own business or making a big change in your life, it’s normal to go through imposter syndrome.

One way Caroline deals with self-doubt before starting something new is to acknowledge how much she’d regret not doing that thing. Yes, it’s scary to navigate uncharted waters, but it’s much worse to have never dipped your toes in those waters and always wondered “what if.”

For Jason, dealing with imposter syndrome and self-doubt comes down to challenging his own assumptions. Put your doubtful thoughts to the test and don’t let them impact business decisions or life choices until they prove that negative assumptions are correct.

Don’t let self-doubt hold you back from getting started and don’t compare where you are on your journey to the end of someone else’s journey.

QUESTION FOR YOU: What self-doubt in life or business can you challenge this week? (Feel free to comment with your answer on YouTube).


Episode “Sponsor”

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It’s Okay If You’re Feeling Lost

June 24, 2018

Over the years I’ve dealt with feeling lost on many occasions. Whether it was taking my first step into the world of entrepreneurship (working for myself) or leaving behind a “successful” business (IWearYourShirt).

Feeling lost seems to be part of the human equation. Something we all have to deal with at different times in our lives, whether we like it or not.

I felt the most lost after an amazing weekend in Fargo, North Dakota in 2013 at Misfit Conf.

In May 2013, I attended a small conference in Fargo, North Dakota. I’d never been to Fargo before and the only thing I knew about the conference was that I was a speaker, and it was going to be a small, hand-crafted event put on by my friends AJ and Melissa Leon (of Misfit Inc).

Feeling lost at Misfit Con, Jason Zook and Srinivas Rao

Backing up for a moment, at the time (May 2013) I was running my IWearYourShirt business and things were in a huge state of flux. Actually, let’s just call it like it is: My business was failing completely and I was 100% burnt out.

My IWearYourShirt business had been my life-blood for the previous five years. It changed me as a person. It brought me amazing opportunities in life. It taught me so many lessons about running my own business. It also helped me build my first (awesome) community of friends, followers, and customers. But IWearYourShirt also took over my life, robbed me of all my time, and left me $100,000 in debt and 50 pounds overweight.

When my wife and I boarded the flight from Jacksonville, Florida to Fargo, North Dakota, I knew I was at a breaking point. Something had to give, I just didn’t know it would happen in front of a room full of strangers.


Why Was I Feeling Lost And How Did I Overcome It?

Let’s back up even further for a moment. In 2007 I left the 9-5 corporate world to start my first entrepreneurial venture. I took a huge risk to leave a super comfortable career as a web designer, to start my own design company with a friend. I had my first inkling of feeling lost at my comfortable 9-5 job. I felt out of place sitting in a beige cubicle. I felt incredible resistance to mundane meetings. I certainly didn’t see my work as meaningful, nor was I ever proud to share it with anyone other than my boss (for his approval, so he’d keep paying me).

I felt the least lost when I was in control of my day and my decisions.

As it turned out, working for a corporation or in my own first design company I realized I wasn’t really passionate about web design, websites, finding great clients, or any of that. I found that I liked working for myself and calling all my own shots. I felt the least lost when I was in control of my day and my decisions.

During the year and a half that I ran my own design company with a friend, the idea for IWearYourShirt came to me. I remember that idea giving me an incredible feeling of purpose. It wasn’t even a business yet, heck there wasn’t even a logo for it, but the idea itself gave me hope. It gave me a direction to go in. It gave me something that felt bigger than myself and something truly unique.

The first time I ever got over the feeling of being lost was when I chased a big idea and allowed it to have space in my life.

An emotional meltdown actually helped me deal with feeling lost

Having a mini emotional-meltdown on stage in front of a room of strangers helped me realize I was lost and forced me to start dealing with feelings I’d been internalizing.

Getting back to the beginning of this story, being a speaker at Misfit Conf presented me with a weird opportunity. I wasn’t new to public speaking and sharing my IWearYourShirt story with a room full of strangers, but this was the first time when I felt like I would be a fraud if I pretended everything was okay. If I just stood on stage and spewed the same stories I’d done the previous few years at countless speaking events around the country.

Instead, as I took the stage in front of 100+ people I didn’t know, I decided to admit I was feeling lost.

I remember sitting on a chair and saying out loud, “Normally I’d tell you all the good things I have going on in my life, but I can lie to you or myself any longer. My IWearYourShirt business is failing and I have to be honest about it.”

I don’t remember the next 45 minutes of my talk. That’s the honest truth. All I remember is snapping back into focus, seeing a room full of people with tears in their eyes, standing and clapping, and me feeling an incredible weight lifted off my shoulders.

For the first time in five years, I’d told a group of people that things weren’t going well. Every day prior to that I’d put on a face and a show.

I’d pretended and forced myself to say that life was perfect. I thought if I didn’t do that my community would abandon me and no one would pay me money ever again.

I stepped off the stage to a group of 100+ strangers who welcomed me with open arms. Where I’d been thinking people would ridicule me for admitting things weren’t going well, I was instead met with love and encouragement (truthfully I think Misfit Conf was the best possible place I could have had this emotional meltdown – that group was/is something really special).

When you’re feeling lost, something has to change

I had been dealing with feeling lost for months (maybe even years) leading up to that talk in Fargo, North Dakota. But instead of trying to acknowledge being lost, I suppressed my feelings and didn’t change anything. I tried to strong-arm my way through my problems, not realizing that I was merely putting tiny band-aids on a gaping open wound. When I took the stage, poured my heart and soul out, and was accepted for my failings, it was as if a switch was flipped.

My wife and I boarded our flight back to Florida and we spent the next few hours talking about everything we’d change.

  • Our spending habits
  • We’d get rid of the clutter in our home
  • I’d be more open with my feelings
  • We’d shut down my IWearYourShirt business for good

Let’s be honest with each other: Change is f*cking hard. It just is.

But without change, I realized I’d just keep digging myself further and further into a hole. I’d ignore problems and I’d hurt myself and the people around me that I cared about most.


How To Find Yourself Through Embracing Minimalism

At that same conference, another speaker took the stage and his name was Joshua Fields Millburn. With his beautifully coiffed hair, he spoke about his life and how lost he had been at certain times. His story really resonated with where I was in my life and I was eager to learn how he solved his own issues.

That’s when I learned about minimalism. Not about getting rid of everything you own and only having one chair in your entire home, but looking at everything you own (and choose to spend your time on) and deciding if those things are actually bringing you value.

Decluttering our home helped us combat feeling lost

It may sound silly to say that getting rid of a few household items made me feel empowered, but it’s absolutely true. The stuff we surround ourselves with takes more of a mental toll than we can see. When YOU are the one to remove something from your life that is no longer serving you, it feels great.

My wife and I started with our closet, getting rid of garbage bag after garbage of clothing we no longer wore. Clothing from our time in college. Clothing from when we were another size in our lives (damn you teenage slender years!). Clothing that we bought on a whim because we thought retail therapy would make us feel better about the things we had going wrong in our lives. It may be hard to believe, but my wife and I spent multiple hours in our closet laughing our way through getting rid of mountains of unused items.

Jason Zook and Caroline Zook embracing minimalism

From our closet, we moved on to other rooms in our home. It didn’t happen in one weekend. Our process of decluttering took weeks/months. But then I decided it was time to apply minimalism not only just to the stuff in our home, but also the business we ran out of our home: IWearYourShirt.

On May 6, 2013, I shut the doors to my IWearYourShirt business. As weird as it may sound, posting a status on Facebook about closing down my business felt better than most things had in my life at that time.

We re-painted our office, which was decorated for IWearYourShirt and all the videos I had been filming on a daily basis at that time.

IWearYourShirt Office, 2013

Rolling white paint over years of memories was equal parts sad and exciting. With each stroke, I felt like I moving toward a new life and new direction. Every brushstroke was one move closer to taking control back in my life.

From that day, we’ve continued to embrace minimalism in our lives. We sold everything in our home and kept only what we could fit in our small VW SUV and moved clear across the country to California. We’re proud to call ourselves minimalists, and we have way more than one chair!

Okay, truthfully, we only own three chairs and two stools, but that’s all we need.


Four Ways To Overcome Feeling Lost And How To Find Yourself

In 2014 my wife and I ventured back to Fargo, North Dakota for our second Misfit Conf. We spent the entire previous year rebuilding our lives and businesses. Getting rid of the things we no longer needed, and for me, sharing more of the thoughts and feelings I was keeping pent-up.

We hadn’t fixed everything in our lives, our businesses were still in flux, we learned three valuable lessons after our second weekend in Fargo:

Lesson #1 to avoid feeling lost: Give yourself permission to do the things you want to do

We all have ideas, goals, and dreams, but most often we are the ones limiting ourselves from making those things happen. It’s not money, timing, or any other factor, it’s giving ourselves the permission to just get started.

I wasn’t able to accomplish what I’d accomplished in the previous year because of luck or good timing. I intentionally changed things in my life and “sat in the chair” as Joshua Fields Millburn says. It wasn’t easy for me and it probably won’t be easy for you. The key is to make a commitment to yourself and to not do it alone. As proud of a person as I am, the best thing I did was give myself permission to start asking for help and being open to the change that comes with that help.

My wife Caroline deserves so much credit here. Not only because she was my biggest cheerleader in me giving myself permission to shut down my IWearYourShirt business and do other things, but also because she is so emotionally tuned-in and could help me navigate the thoughts and feelings I was having.

Lesson #2: Stop being so proud

I was too proud to ask for help. I was too proud to think I could figure everything out myself. I was too proud to ask people smarter than me for advice. I was just being too damn proud.

After the second year attending Misfit Conf, I decided to let my guard down a bit in hopes of figuring some things out about myself. I’ll be the first person to admit that I used to shudder at the idea of reading a self-help book or talking to a coach of any kind.

Acknowledging that I was being too proud made me feel like I was at least taking the first step toward working on these things.

I’m not sure where my too proudness stemmed from. I can’t remember a specific story from my childhood, but I’m sure there’s something there. Nevertheless, I remember being stubborn from a young age and I needed to change that. I needed to let go of trying to be in control of everything, especially my emotions.

While I do see pride as a useful tool in certain situations, it can also be a detriment if you have too much of it.

Maybe you’ve been too proud in certain circumstances that led to a fight with a loved one or a bad business decision?

It might be time to admit this to yourself and attempt to make a change.

Lesson #3 in how to find yourself: Stop trying to answer “what do you do”

This may sound dumb, but maybe you can relate. The question “what do you do?” had thrown me for quite a loop since 2009. Explaining IWearYourShirt to a random stranger in an airport who wanted to make idle chit-chat? That was always a hot mess.

I started to really resent the question especially after I shut down my IWearYourShirt business. I didn’t have an easy answer that quickly explained my weird entrepreneurial endeavors and each time I was asked thoughts of doubt and criticism swirled around in my head. I started to wonder why this question was bothering me so much and if there was a way I could fix it?

After multiple conversations with my wife, we both decided I should just accept that I was in a time of flux and experimentation. Sure, I didn’t have an easy answer at a cocktail party that could quickly define who I was and what type of work I was doing, but that started to not matter once I allowed myself to be doing a “floaty dance through life” (as my buddy Ben Rabicoff put it).

Once I came to terms with the fact that I didn’t need a clear definition of what I did for work to give me self-worth, I started to be more accepting of myself.

Lesson #4: Writing is cathartic

I never thought I’d be a writer. Heck, even as I type these words to you, it feels incongruent to the person I pictured I’d be in life. But alas, here I am. A writer. Someone who has typed millions of words, thrown the majority of them away, self-published a book, and written for many major publications. But it didn’t start that way.

Writing became my form of personal therapy.

My journey with writing consistently started with writing little blog posts about life and things that weren’t going so well.

I was incredibly nervous to hit publish and to share the first blog post I ever wrote that was the least bit vulnerable. But guess what happened? People celebrated my honesty. They didn’t critique all the bad grammar and poor sentence structure. They simply appreciated that I was willing to go out on a limb and to share something many people might not.

My writing went from a random blog post here or there from 2012-2013 to a consistent weekly post and email in 2014 to a small group of subscribers (just 400 people). Also in 2014, I self-published my first book, Creativity For Sale.

Writing a book was one of the most cathartic things I’d ever done in my life because I got to finally share so many stories of failure and mistakes that I’d kept bottled up inside.

In 2015 I started writing for Inc Magazine and a few other notable media outlets while continuing to write for my own audience (a group that became known as the Action Army). In 2016 and 2017 I stopped writing for anyone else and only wrote for my own audience on

In just a few short years I went from writing random updates on a Tumblr blog to having over 500,000 people read my writing in 2017. Can you believe that? It’s hard for me to believe!

Maybe writing could be an outlet for you? You don’t have to start by publishing your writing. Maybe it’s just a journal you keep? Or a daily writing practice you do for one hour per day that lives in a Google Doc that only you know about? Give writing a shot, it was instrumental in helping me overcome feeling lost.


Feeling Lost Is Something We All Deal With, Don’t Try To Get Through It Alone

While I do believe some solitary activities can help, like writing, if you’re currently feeling lost you should absolutely reach out to someone. Is there a peer in whatever industry you’re in that has been down a similar path to you? Or maybe finding a therapist in your local area that is highly well reviewed? Therapy has such a negative connotation, but people like my wife swear by it (and we celebrate its effectiveness in our house!).

We all deal with feeling lost at certain points in our life. And I hate to be the bearer of bad news, but even if you overcome a big milestone of feeling lost like I did in 2013, you’ll be met with more bumps along the road.

If you want some book recommendations, I’d highly recommend The Obstacle is the Way and Body of Work. Both of those books were really helpful for me and continue to provide lessons for my life.

I’d also highly recommend giving minimalism (your own flavor of it!) a try. Decluttering your life can lift more weight off your shoulders than you’d ever imagine.

You aren’t on this journey called life alone. There are people around you who want to support and help you. Be willing to open up to them and be willing to ask for help. It was difficult for me, but it was also the best thing I’ve ever done.

How To Deal With Comparison and Finding Confidence When You’re Lacking Experience

June 18, 2017

The questions in this post came straight from Made Vibrant readers in my email community, Self-Made Society. If you’re not signed up yet, do so here! I asked subscribers to write back with one question they have for me, and I received dozens of responses, spanning topics like my creative process, creative business revenue streams, email list growth and marketing, pricing, and personal motivation. 

I tried to answer them all by breaking them down into categories. This group pertains mostly to confidence and the creative mindset. 

On dealing with comparison…


“Do you have a specific practice to help yourself when you start comparing your journey, yourself or your gifts to others?”

— Submitted by: Rachel S.


For a long time, honestly my strategy for dealing with comparison was just to try and avoid it altogether. I’d be on social media and scroll past a photo of a fellow artist that made me feel like my work wasn’t good enough or I’d start comparing my journey to theirs, and when I recognized the presence of that feeling, I’d simply hit unfollow. I thought, You can’t feel bad about what you can’t see, right?

But I knew that wasn’t a winning strategy forever, because in doing so I wasn’t actually confronting the source of that comparison: me.

Comparison is a natural part of the human condition. It stems from our deeply rooted biological wiring that tells us there are limited, finite resources and we need to be on alert to compete with those around us for those resources to ensure our survival. While this is incredibly helpful when we’re all cave people living off the land, it’s NOT very useful when we’re cultivating our creativity.

Finally I’m now entering a phase where I have enough confidence in what I’ve created these past few years that I don’t need to avoid comparison anymore. In fact, now I use that feeling as a guidepost, bringing my awareness to my own desires. When I scroll past an artist or fellow entrepreneur and I have that feeling, now I can ask myself: Where is this coming from? What it is that I see that person doing or having that I feel envious of or that makes me feel less than?

Is it that they’ve developed a unique and distinct artistic style? Great, then I know I just need to create more things to work on that. Is it that they have dozens of comments from fans who love their work? Cool, then maybe it’s time to prioritize my community more. See what I mean — I still experience that feeling, but now I can recognize it and use it as a motivator to keep creating (without beating myself up.) I don’t let comparison discourage me, I let it encourage me to keep going, to keep working.

**In short: If comparison is holding you back from creating, then do yourself a favor and block it out to focus on your own work. Keep your eye on your own journey, and don’t waste any precious time focusing on others. Cultivate confidence in the things you DO have, rather than what you don’t. And if you’re at the point where you’re ready to widen your view again and keep tabs on what peers are doing, then consider using that feeling of comparison as fuel to push you toward the desires that are still within you.**

Further reading: What To Do When Comparison Kills Your ConfidenceAre You Limiting Your Possibilities with a Scarcity Mindset?Room For Us All

“Consider using that feeling of comparison as fuel to push you toward the desires that are still within you.”

On creating with depression (or, in my case, anxiety)…


“I was wondering if you have any tips/ideas about designing with depression. Or more accurately, dealing with depression while designing. It’s really hard for me to keep my creativity when I’m having a rough time and it kinda shuts down almost completely.”

— Submitted by: Perlin A.


As much as I wish I had a definitive answer for this, I don’t want to belittle the struggles of depression by pretending I know what it’s like to try and design with depression. I don’t. However, I do struggle with anxiety. Two years ago I went through a period when I was starting my business where it got so bad it was affecting me on a physical level — dizziness, chest pains, shortness of breath. Every day it was all I thought about and it made working really difficult. The worst part was feeling like it would never get better. That every day was going to be like that going forward.

I don’t know what brought about the change for me — maybe the exhaustion of living like that for a few months — but finally I said to myself: What if I just try convincing myself that it WILL get better, whether I believe it at first or not? What if I operate on the assumption that things WILL eventually improve?

That shift in perspective was enough for me to start making the tiniest moves to climb out of the hole I felt in. My new belief freed up enough hard drive space in my brain that I could start to see the changes I needed to make to at least limit the things that were causing me anxiety, and to be more discerning with the projects I took on.

As for how this applies to your story, my advice would be to first try my trick of convincing yourself that it won’t always be this hard. You may not even believe yourself at first, but trust me when I say that the underlying belief will give you a tiny bit of relief which you can use to free up a bit of energy and clarity. Then, I’d also say get really acquainted with yourself and your intuition. In my guide Connecting With Your Core, I talk about developing a language between your head and your heart. If you can develop a sense of mindfulness within yourself and clue into even the slightest things that either lift your mood or keep you feeling shrouded in depression, then you can take actions to do more of what lifts you up and less of what keeps you down.

On a more practical level, my guess is that it’s not very predictable when you’re going to be feeling motivated to design or when you’re going to need time to take care of yourself. I know there are many MV readers that also have chronic illnesses and can relate to that. Because of that unique circumstance, I recommend coming up with a work process that allows for extra flexibility and time cushions. Maybe you take your design timelines and build in a few extra days when working with clients. This means that if you wake up one day and you’re not feeling it, you can focus on some other aspect of your work that doesn’t take quite as much brain or will power.

**In short: Believe that it will get better. Build in time and processes that allow for flexibility, and give yourself permission to take care of yourself.**

Further reading: Connecting With Your Core

“Build a process that allows for flexibility, and give yourself permission to take care of yourself.”

On finding the motivation to course correct…


“When you are in a ‘I don’t like what I’m currently doing.. what’s next for me’ phase…. What helps you take action?”

— Submitted by: Phil Aube


Well, maybe this isn’t the most relatable answer but it’s the honest one! Here’s one gift-slash-curse that I’ve always had deeply embedded in my personality: once I make the realization that the current path I’m walking is the wrong one, it becomes actually painful for me to keep going down that path. Painful in this sense just means my core self feels so uncomfortable and resistant that it’s all I think about. I’ve become so intimately acquainted with my own core self and what it wants that when I’m out of alignment, it’s like my own inner voice is screaming at me “TIME TO CHANGE COURSE!”

So to answer your question, what helps me take action is the recognition that the sooner I course-correct, the sooner I alleviate that psychic pain. Even if making that shift is uncomfortable (which it always is), I just remind myself that staying stuck on the wrong path is the MOST uncomfortable thing because to me it feels like a waste — wasted potential, wasted time. We only get a certain number of moments on this earth and I intend to spend mine wisely (aka BRIGHTLY.)

**In short: Ask yourself what’s more uncomfortable: taking action to get back to a path where you DO enjoy the way you’re spending your time (and life) or continuing to waste minutes and days and months doing something you know is out of alignment with what you truly want? Then, use that answer to motivate you to action.**

Further reading: The Clarifying Power of Regret

“What’s more uncomfortable? Taking action to get back to an aligned path or continuing to do something you know is out of alignment with what you truly want?”

On balancing the less exciting parts of a creative business with the things that light you up…


“How do you refocus when you feel like you’re just ‘checking boxes’ in your business? I understand that every day I’m not going to be completely passionate about every aspect of my business and some things are going to make me uncomfortable and I’m just going to have to DO THEM. But I also realize that energy and sharing my passion about something is what attracts people and I’m MORE effective when I’m passionate, white hot and excited.”

— Submitted by: Dr. Lauren Frauenheim


I feel like this question is at the heart of what it means to run a soulful, heart-centered creative business! The foundation of your question is how to balance things that are necessary but less than stimulating in your business with the things that really light you up and get you excited.

Honestly, this is a toughie for me because I think the answer is different for every person and where they are with business! I will say that I don’t believe anyone, especially solopreneurs, can run a business and be on fire with excitement for every single task in keeping up that business. That’s like online biz utopia and I’m just not sure that’s practical for most of us. The key, then, is in making sure that the aspects of running your business that you’d consider merely “checking boxes” are not stealing precious energy from the heart-aligned aspects. What I mean by that is,  while a task like emailing clients/customers maybe not soul-stirring or get you fired up, you just want to make sure that task is not soul-DRAINING. If there are aspects of your business that are actually taking a negative toll and preventing you from shifting your energy to that white hot excitement in other aspects, it’s time to rethink those tasks. See if you can outsource them or reframe them or do away with them altogether and change up your process to minimize that kinds of energy-zapping.

On a more macro level, aside from just daily tasks, there may be times that you find yourself in a “checking boxes” phase altogether — a time when you have to hit pause on the more creative and exciting projects in order to focus on ideas that are less exciting but more predictable in terms of income. This could be because you’re in a tight financial spot and you need to focus on bringing in some immediate cash so that you have the breathing room to feel excited again. As a creative who has found herself in that phase on more than one occasion, I think it’s perfectly normal. After all, we can’t do our soul’s work to our best ability when we’re worried about paying the bills all the time. So I think it’s totally helpful to give yourself permission to focus on the more “business-y” goals for a second in order to make breathing room for the white hot excitement. (And hey, if those things are one in the same, well more power to ya!)

**In short: Not every aspect of your business is going to light your soul on fire with excitement and come flowing out of you with ease. That’s okay. Just make sure that whatever those less-than-thrilling aspects are, that they are a) not negatively impacting your spirit and b) at least helping you get to place and a greater goal that DOES light you up.**

Further listening: I go into these ideas more in-depth in my interview with Tiffany Han on her podcast, Raise Your Hand Say Yes.

“The key is in making sure that the necessary mundane tasks are not robbing your soul of the joy it feels overall in your creative business.”

On finding confidence in your own creative process…


“How do you start a branding or an illustration project when you have a great idea of a theme, but you don’t have any clue how should it look?”

— Submitted by: Zsuzsanna Németh


The first thing I’ll offer up to you that might be a helpful mindset shift is this: there actually isn’t a way something “should” look. That’s what YOU get to create and decide! The whole fun of branding or illustration is uncovering the creative solution to a project throughout your process, whatever that might be. So perhaps it might free your creativity up a bit to start viewing your process in a spirit of openness as though it’s a discovery, rather than a linear path from idea to execution/solution. Viewing it in the latter way — as if you’re “trying to find the right answer” — puts pressure on you to hit a bullseye versus being open to new ideas and discoveries.

Something that also might help you is developing a clear process for yourself to help you get from point A — like a “theme” — to an end product. For example, in my branding process, I have many different “checkpoints” along my process that carry me through to a final brand. I begin with a conceptual brief, then I decide on five tone words, I create a mood board, pick out exploratory colors, then choose typography, design a logo and round it out with graphic elements. Each part of that process is like another tiny ingredient or piece that I can add to my branding stew, which helps me land on a “flavor” that feels right rather than just trying to go from a general theme and stare at a blank piece of paper (or Illustrator art board!)

**In short: Break your design process down into bite-sized stages and allow yourself to be open to possibilities during that process. The more you can view your work as a discovery process rather than a test, the less pressure you’ll feel and your creativity will be free to express itself.**

“The more you can view your work as a discovery process rather than a test, the less pressure you’ll feel. ”

On teaching yourself a new creative skillset without becoming overwhelmed…


“I have always had an interest in graphic/web design, and decided to start pursuing that as a career. My original thought was to go back to school… but I’m now going with Plan B, which is teaching myself. Sounds awesome in theory, but lately, I’ve been feeling overwhelmed and discouraged – there are SO many different classes to take and programs to learn that it just makes me want to take a nap and forget about it! There’s also the recurring feeling that most creatives have of, ‘LOL there’s no way I can do this and come out as talented as these people I’m looking at on social media.’ “

— Submitted by: Nicole S.


As far as the idea of “I’m not as talented as these people on social media,” that kind of comparison is natural when you’re starting out, especially when you’re self-taught. See my earlier answer about comparison on that front!

I did also want to offer up some advice about teaching yourself graphic and web design, which is what I did! In the beginning, it’s all definitely very overwhelming: Which programs should I learn? Are my skills good enough, etc? Most people make the mistake of thinking they need to learn everything under the sun and master all the programs, which can oftentimes leave you feeling, as you said, like all you want to do is take a nap! My advice is to start with one very specific skill and one program in mind to learn. Once you get comfortable and master that, you can layer in new skills and new applications over time, as the opportunities pop up.

For example, I started out learning photoshop so I could create graphics to spruce up my blog (this was back in 2011!) Since I had a very specific program (Photoshop) and a specific reason for using it, it helped me seek out the online courses and resources that pertained to that one thing. Then I learned how to create blog post graphics, then a new blog logo. Once I felt comfortable, more people were asking to hire me to do their branding and I felt it was time to expand my skills to Illustrator. The same thing happened when I got a big branding project and they wanted a Brand Guidelines PDF — that’s when I felt it was time to invest in learning InDesign to create a document like that.

**In short: Start with one specific skill and program to teach yourself, then upgrade or evolve your skills as the circumstances require more of you. Keep expanding your portfolio as you keep creating work. Narrowing your focus will help you fight that feeling of overwhelm, and the only remedy for comparison syndrome or lack of confidence is to keep creating until you believe in your voice and your own work.**

Further reading: Follow Your Curiosity And It Could Change Your Life

“Start with one specific skill to teach yourself, and upgrade or evolve your skills as the circumstances require more of you. ”

On figuring out the entrepreneurial path that best aligns with who you are…


“My question is all about how to start the entrepreneurial journey. I’ll soon be out of college and would love to start by own business(es) but I’m quite lost regarding what to do… where to find the clients, and especially how to convince them I’m adequate enough even if I’m new-ish (but know I can do a good job nonetheless because I have the skills). Actually I modify that first part: not how to find what to do but how to prioritize as well so that it aligns with you!”

— Submitted by: Camila R.


Here’s the thing about starting out and know what aligns with you. Unfortunately there’s just no other answer than: experiment. When you’re fresh out of college, those first few years you are changing SO much. You’re figuring out where you want to live, who your friends are, how you want to spend your time, etc. so that target of alignment is going to be constantly shifting. To really know what you want at any given moment, you’ll need to engage in all kinds of things and activities. The best advice I can give you in the regard is to PAY ATTENTION. Get to know yourself, your intuition, and the signals your body sends you. What kinds of activities feel freeing and which feel confining? That will help you navigate and course-correct as you move forward.

As far as turning all of that into your own business, yes, it can be hard when you’re starting out and you don’t have that much experience. (You may know that your skills are good enough, but you also need to show that to others if you want them to pay your or hire you.) Just remember that you are in control of how much experience you get. If you believe in your skills (and it sounds like you do) but people won’t hire you without experience, find time to take on small projects free of charge. Ask for testimonials. Hone your process. Use those experiences to build a portfolio so that when you do try to get paying clients, you have something to point to. Everything will likely feel uncertain in the beginning because you’ve never done it before but the more you’re able to withstand that uncertainty, the faster you’ll be able to get that experience and the more confidence you’ll have in charging what you’re worth.

**In short: Learn what you want and what feels good to you by experimenting. Test the waters on many things, and prioritize accordingly. If you’re worried about lack of experience, take on small projects for free to build a portfolio. Don’t just tell people what you can do, show them.**

Further reading: 5 Crucial Steps To Building A Profitable Online Business (see especially point #4: Do the work.)

“Learn what you want and what feels good to you by experimenting.”

On honing your creative voice…


“How long did it take to get your “voice” dialed in? Did people respond right away or did you have to make stuff for a while until you got it right?”

— Submitted by: Katy S.


I would say that the first iteration of trying to hone my creative voice was when I started my first blog back in 2011. For the first three years or so I didn’t really feel like I knew what my voice was — what I wanted to talk about, what made me different, how I wanted to write. But the best decision I made back then was to write on a consistent basis, because that’s how I was able to not only get better at infusing my personality into my writing, but to look back over the course of time and find patterns.

To answer your question specifically, no people didn’t respond right away. There was a long part in the beginning when I was really just experimenting and figuring things out, without expecting anything in return from readers. Then, I feel like once I got some clarity on my message and my voice, I started communicated with more confidence. That allowed me to attract an audience of people that “got it” and that’s when the response started to happen. People started to resonate. But it all begins with that exploration and clarity phase. It begins with letting go of perfectionism and the fear of “getting it wrong.” If you’re able to start from a place of curiosity and embrace the messiness of the beginning, that’s when you’re on the journey to finding your voice. It’s about finding what YOU love and what you want to create. Once you have a better sense of that, share with confidence to a clearly-defined audience and things will surely start to resonate.

**In short: Finding your creative voice takes exploration and creating with consistency. Once you narrow in on what you want to share and your unique way of sharing it, doing so with confidence to a clearly-defined audience is the recipe for creating something that resonates.**

Further reading: 5 Tips For Uncovering Your Unique Creative Voice

“Finding your creative voice takes exploration and creating with consistency.”

On the value of experimentation..


“If there’s one vital/helpful information you hope you knew before you started this journey, what would it be?”

— Submitted by: Lyndee Katanyag


Great question! SO many things! But if I had to boil it down to one impactful thing, I think it would be this reminder: Life is an experiment.

I’ve written about this many times in different ways (like here and here) but the main reason this is a powerful guiding force for me is just that it reminds me that you won’t know unless you try. Every person, every business, every life — we’re all different. The advice or blueprint that works for one person doesn’t always translate to another. We’re all looking for the roadmap not realizing that no one holds the right one because no one has ever lived THIS life, THIS way, at THIS particular time before. So the only real way to know what feels right in your gut, or what works for your business, is to get out there and experiment. Create, test, try, fail, and learn from the results.

There are still times when I find myself stuck thinking and strategizing and standing still, afraid to move forward because of the What ifs. And I KNOW there are SO many creatives with so much potential out there right now, afraid start the blog or start the business because they don’t know if it’s the right thing. What they don’t realize (and what I had to learn) was that ANY move you make is ultimately the right one because just one step forward in reality (even the wrong step) will teach you far more than standing still or moving forward only in your mind. We can make all the assumptions in the world but until we actually run the experiment, until we actually do the thing, we won’t really know the outcome.

This one phrase also reminds me that the variables in this experiment of life are always changing. If my aim is to design a life and business around my values, then I have to constantly be checking in with myself to ask what those values are. I have to understand that I myself am a moving target and sometimes the only way to know if something aligns with my vision for my life is to simply go out there and try it. If I fail or if I decide it doesn’t feel right, I can remind myself that it’s still a win because I learned something from the experiment.

**In short: To learn, you must DO. And to do, you must embrace experimentation. The circumstances for the experiment of life are always changing, so give yourself permission to evolve along the way.**

Further reading: Life Is An Experiment; How To Embrace Experimentation In Your Creative Business

“To learn, you must DO. And to do, you must embrace experimentation.”

Hope you enjoyed this Q&A post — more installments coming soon!

Challenge All of the Assumptions, Especially Your Self-Limiting Ones

May 7, 2017

Whether you’re looking to succeed in business or make changes in your life, the first step is to challenge your assumptions.

Our brains have this mystical, magical, and commanding power over us. We know this. We even acknowledge it. But it can be incredibly difficult to challenge our own thoughts.

Phrases like “I don’t think this will work” or “I don’t know what will happen” are assumption-based.

We give our assumptions more authority and power than they deserve when trying to make decisions and take action.

I’d like to tell you I’ve come up with a perfect framework for you to test all your assumptions and never let your assumptive thoughts dictate your decisions again. But I haven’t. Maybe someone way smarter than me does, but all I have to share is a life of assumption-challenging experiences.


How To Challenge Assumptions When Starting A Business

I’m amazed at how often I hear from people who are talking themselves out of being successful (a term, for which, you must define yourself, not based on any outside metrics). They use phrases like these:

  • “My idea has already been done before”
  • “I’m not special. Why would anyone care what I have to say?”
  • “I don’t have the skills required to make my idea happen”
  • “I can’t make money doing what I want to do”
  • “I don’t know where to start”

Let’s attack these assumptions together.

“My idea has already been done before.”

AWESOME! That means the market is proven for this product or service. People are already paying for it. The assumption you’d want to test (people being willing to buy this) has already been proven for you, and you don’t have to scale the huge mountain of trying to prove that there are actually people out there who will pay for your idea. It’s a good thing that there are are virtually ZERO new ideas left. Our species is too smart. Everything is just a remix of other ideas at this point. Embrace what makes your remix of an idea unique.

“I’m not special. Why would anyone care what I have to say?”

Whoever told you that you weren’t special was an a-hole. You are special. I am special. We are special little snowflakes. Now that we’ve gotten that out of the way, being “special” isn’t what’s going to help you succeed, anyway. No one lines up to buy the newest iPhone or pair of Air Jordans because Steve Jobs or Phil Knight are special people. They are special (just like you and I are), but the blood, sweat, tears, work, sacrifices, failures, mistakes, and assumption-testing thinking is what’s led to you wanting to buy the product they’re producing. People will absolutely care what you have to say. You just have to understand it may take years for you to find the right, resonant way to say it. You are significant.

“I don’t have the skills required to make my idea happen.”

I have virtually NO specific skills. I’m a jack of all trades, master of none. I dabble in design, but I’m years behind designers whose work actually receives praise and accolades. I don’t know a thing about programming languages. I’m terrible at managing people. Really, you could argue, all I have are my ideas. But yet, I find ways to turn my ideas into realities. I seek out people to whom I can outsource my weaknesses. If you really want your ideas to happen, the skillset you have doesn’t matter one bit. The only skill you need is the work ethic to figure out how the heck you’re going to get your idea out into the world. Someone else in the world knows what you don’t. Find them. Pay them money. Exchange something for their time. No skills required.

“I can’t make money doing what I want to do.”

Why not? Because other people haven’t been able to? Because others already have? Those are other people, they aren’t you. I’m never willing to accept assumptions based on the actions of others. This is a blessing and a curse. But you can make money doing literally anything right now. I once wrote a silly joke in an email about becoming a professional snuggler. Then, a few weeks later, I received an email from a woman named Sam who actually created a popular Snuggling Agency because of my silly joke (amazeballs!). I’ve made money doing weirdly outlandish things. My name has been included in segments on TV called “they get paid for that?” and “jobs you never thought you could get paid for.” As the old adage goes, you won’t know until you try. And as it relates to making money doing what you want to do, you absolutely won’t know until you try (and try in all the different ways that other people haven’t thought of before, or in ways they haven’t done it as well as you will).

“I don’t know where to start.”

By reading this article, you are starting. By wanting to start, you are starting. But those things aren’t enough. Eventually, you just have to put one foot in front of the other (or click a mouse one click in front of the other). Because guess what? I didn’t know how to start, either. I still don’t know how to start most projects, but I do it, anyway. I find my way by giving myself permission to start ugly, learning all I can, and then trusting my intuition along the way. It looks different every time, but the important part is that I start at all.

There is no straight line to success

Our culture loves to tout the successful. Magazines, TV shows, movies, and websites love to glamorize how people “made it” and “became so insanely rich they turned into a pile of money and flew off in the wind.”

People assume success is a straight line. You start on your little dot on a map. Then you cross a single line, and you’re at the X. Success!


Success looks like a treasure map.

You follow a dotted line that twists, turns, curves, hits all kinds of obstacles in your way, and eventually you find the X (maybe).

Treasure Map illustration by Tim Vandevall

(Treasure map illustration by Tim Vandevall)

The unfortunate thing about the treasure map to success is that sometimes you get shipwrecked. Sometimes you get stranded. Sometimes your only friend is a volleyball. No one can predict when you’ll get marooned on a deserted island (read: when you will have a mistake or failure). But it will happen. It happens to everyone at some point or another.

Just like testing all your assumptions, if you accept the fact that success looks like a treasure map, you’re going in the right direction. You will veer off path. You will hit roadblocks. You will have challenging moments when you question the entire journey altogether, but the journey wouldn’t be worth it if you didn’t.


Why You Should Test All Of The Assumptions All Of The Time

As I mentioned, there’s no framework for getting better at testing your own assumptions. All you can do is make the decision to start testing all your assumptions (and the assumptions of society, your friends, your family, etc.) all of the time.

I don’t assume anything will work a second time around. I don’t assume that just because I read something in a book that it will work for me. I don’t assume that because someone else does something a certain way that’s how I need to do it.

I test those things. One by one. Assumption by assumption.

Here’s one question that always helps me when I’m on the dotted line of my treasure map and being met with an assumption:

“Have I dealt with this exact issue before with the same exact circumstances?”

Almost always, the answer is “No.” It’s nearly impossible for the answer to be “Yes.” And because the answer is “No” you have to test your assumptions. Sometimes, it feels like you’re re-testing assumptions you’ve already re-tested in a re-test of assumption re-testing before. Well, welcome to life and business. It’s not a straight line. It gets pretty damn windy, and you’d better hold on for the ride.

My wife, Caroline, and I have some of our most emotionally charged discussions when testing assumptions. We typically use the three whys:

“Why does it have to be done this way?”

“Why do we have to run our relationship the same way as other people?”

“Why do we ever have to do anything the same as anyone else, ever??”

That last one is a troublemaker, and admittedly, must be obnoxious to deal with (Sorry, Carol, love you!).

Constantly testing assumptions in life and business has gotten me where I am today. A place where I truly feel I’ve “made it.”

That’s not because of a certain amount of dollars in my bank account, and it’s definitely not because of a number of friends I’ve amassed on a social media site.

The point here is that I’ve “made it” because I’m willing to question everything (and I have the ability to do so). I am in control of my outcomes and I’ve earned every bit of success I’ve achieved. I could lose everything in an instant, and I’d be okay, because I know what it’s taken me to get where I am today. A place (or some version of it) I could get to again, knowing I’ll have to follow a pretty damn windy treasure map to get there.

The Only Person Who Can Give You Permission Is You

April 30, 2017

It’s time for you to give yourself permission to do the thing you’ve been dreaming of doing.

When I released my first book, Creativity For Sale, I was met with a barrage of messages from people all over the world. They were all inspired to start their own business or pursue an idea they’ve been sitting on for years, which was awesome. Yet most of them felt stuck and weren’t sure what to do next. The question I got most often was (and still is), “What’s your advice on getting started?”

What I’ve come to realize from my discussions with hundreds (maybe thousands) of readers and subscribers asking that question is that they don’t actually need any advice or knowledge. They’re looking for someone to give them permission to start.

We live in a time when anyone can create anything. It’s those of us who don’t need permission who make progress the quickest.


It’s Time To Un-Learn Asking For Permission

We’ve been taught our entire lives that we need to ask permission to do things. Whether that’s permission to go outside and play with our friends (when we’re kids, or big kids posing as adults). Permission from a guidance counselor to take a certain class outside our major. Permission from a boss to veer from the normal corporate strategies or tactics. Permission from a significant other to pursue a side project that has nothing to do with our current work. There are a million things in our life we ask for permission for, it’s no wonder so many people are afraid to take a leap and start a business or chase a dream. No one told us that we don’t have to ask for permission anymore.

When I reply to people asking my advice, I often hear some version of this reply: “This was the exact permission I needed to get started!”

It’s not that I wrote anything amazing. I don’t have a nugget of wisdom perfect for every situation. I don’t even actually grant anyone permission for anything. I just reply, and that’s often the catalyst people need to go ahead and grant themselves the permission they’d been waiting for.

So let’s pretend you sent me an email today asking for advice, and that this article is my reply to you.

We are our own gatekeepers, so let’s stop limiting ourselves

If you want to start a freelance design business right now, you don’t need anyone’s permission to do it. Whip together a website on Squarespace that promotes your awesomeness, your skills, and your work (if you don’t have work, make some!). Email a handful of friends and ask if they need design work. You could do this in the next few hours and make thousands of dollars immediately.

If you want to write a book, but don’t think landing a big publisher is realistic, publish your book your damn self! That’s what I did with Creativity For Sale, and it’s gone on to sell 15,000+ copies. Sure, it hasn’t been a best-seller or on any fancy lists that books get put on, but who cares? If you’re writing a book and your only measure of success is a best-seller list, you shouldn’t be writing a book.

Maybe you want to open a super hipster coffee shop where all the drinks have Saturday Morning Cartoon themed names (like Scrooge McLatte, or Captain Americano, or The Flintspressos). Sure, my examples are awful, and maybe the world doesn’t need another hipster coffee shop, but why not? You could hone in on a super-defined niche of people who absolutely love your crazy idea and want to pay you money for it. Stranger things have happened.

In all of these examples, one of them not-so-great, you’ll never know unless you give yourself the permission to try. No one else needs to approve. Stop locking the gate on your own progress.

Three mini permission slips you can give yourself

#1 Write a message of permission to your future self: Use a service like, Boomeranggmail, or RightInbox to send yourself an email that arrives in one week. In that email, write “I give you permission to start or launch .” You’d be shocked at how powerful receiving a message from yourself can be.

#2 Get permission for an accomplished person: Watch Casey Neistat’s Do What You Can’t video. Then watch it again.

#3 Ask someone you know to give you permission: Send an email to a person you admire and ask them to give you permission for your idea. Sound weird? Well, I think it’s weird that you haven’t given yourself permission yet, so this seems less weird to me!

There will never be a better time than right now

Do you have a crazy idea for a business? Something as crazy as getting paid to wear t-shirts for a living? I launched IWearYourShirt during the recession of 2008. All signs should have pointed to that being a terrible time to launch a weird/unique business idea. But to the contrary, there probably wasn’t a better time I could have picked. People were ready for something weird. People were looking for ways to get attention and get noticed on social media.

Are there almost 50,000,000 books already on Amazon? Yep. But does that mean there isn’t room for your book? Not at all. If anything, it just shows how much people are willing to continue to purchase and read books. Get your book out there, because if whatever you’re creating never exists, you have a 0% chance of succeeding.

Right now is the time to start that crazy business idea. Right now is the time to start your freelance business. Right now is the time to give yourself permission to do whatever thing you’ve been dreaming of doing.

You already have enough skills and resources at your disposal, all you need to do now is give yourself permission and get started.

If You’ve Built Something Worth Saying Yes To, Stop Saying No For Other People

March 4, 2017

I see this trend a lot in the online business world. Well-intentioned folks will build a website and brand, set up social media accounts, have a goal or mission, and spend a ton of hours getting ready to sell.

But then, something happens. Self-doubt creeps in. The second-guessing police show up at the door. Defeated, these well-intentioned people shy away from promoting and selling the thing they’ve worked so hard on. They say “no” on their customers’ behalf…even before the customers can decide for themselves.

If you’re afraid of rejection, go work for someone else

Working for yourself isn’t easy. You have to wear all the hats (and most of them feel like ugly fedoras). You have to juggle all the balls (hehe). You have to be a salesman/saleswoman. People are going to say no to you, because what you are selling is not right for everyone.


If you fear rejection so much that it holds you back from promoting and asking people (more than once) to buy your product, running your own business may not be right for you.

And besides, working for someone else is not a bad thing. Sure, you aren’t going to end up on the front page of Inc. magazine, but who really cares about that, anyway? If it crushes your soul to ask people to buy things, work for someone else who is already doing that asking. Take a paycheck for work you don’t loathe, and live your life in a way that makes you happy.


If You’ve Built Something Worth Saying YES To, Stop Saying No For Other People

You may not even realize it, but you’re saying no for people by staying quiet about your idea.

Silence is golden when you’re a 3rd grader and you need to learn simple math. Silence is NOT golden when you need to put food on your table and get people to purchase your product or service.

I’m not advocating that you start hammering people with marketing and sales messages left and right. But I am advocating that you give your idea a chance. Put in effort, aim for a yes, and actually let people say no on their own so you can learn from the experience.

Remove these things from your mind or vocabulary:

  • No one needs my product or service because other people are already doing what I’m doing.
  • I’m just getting started. I don’t have an audience or any traction to get people to buy.
  • I’m not sure what to ask for, so I’m just going to wait for opportunities to show up.
  • It didn’t work when my friend/colleague/lover tried to sell this thing, so why would it work for me?

All of those are self-defeating thoughts, and thoughts that put the word “no” in someone else’s mouth before they can even do it themselves.

Instead, muster up the courage to promote and sell whatever you’re working on and embrace the actual no instead of the imaginary one.

When you do hear “no,” don’t just hide away to lick your wounds. See if you can learn more:

  1. Why wasn’t it a good fit?
  2. What didn’t they like or understand?
  3. Was the timing bad?
  4. Was the pricing off?

These are questions you should ask the people who say no to you. Don’t look at it as punishment, either. Look at it as a learning experience, and tweak/hone your promotion and sales strategies. Because I’m here to tell you, whatever you’re trying to sell isn’t going to sell just because you have a website, brand, Instagram account, testimonials, etc.

Selling takes effort, so be proud of the fact you’re hearing no because it means you’re actually doing the work.

Stop saying no for someone before they have a chance to.

Related articles: You Don’t Get What You Don’t Ask For and How To Deal With Rejection And Hearing No.

Competition is Good and How To Use It to Your Advantage

February 23, 2017

People often ask if I ever had an “a-ha” moment with my IWearYourShirt business. A moment when I clearly knew it was a good idea worth pursuing.

In September 2008, there was a moment, in my closet, when a culmination of previous thoughts and ideas came together, but that was simply the spark for the idea of IWearYourShirt. And we all know what they say about ideas, right? They’re worthless without execution.

Which brings me to an “a-ha” moment that actually was important.

Competition doesn’t have to be a bad thing. It can be the perfect motivator.

When I first came up with the idea for IWearYourShirt, there was nothing like it. No one had thought of IWearYourShirt in a way that I had packaged it all together in my mind. And certainly, no one was crazy enough to take on a 365-day challenge like I was. At least until November of 2008, when “Girl In Your Shirt” popped up on my radar.

Now, back in 2008, Twitter was a very small space. Yes, there were millions of accounts already, but when you did something that got press on TechCrunch, everyone knew about it. And Girl in Your Shirt got it. Suddenly, she was everywhere.

I remember my first reaction to the TechCrunch story: a mix of fear, jealousy, and utter despair.

I’d clearly had the idea for IWearYourShirt first, but there was no mention of me. No credit was given to my unique idea. Just a girl doing what I set out to do, which apparently was more worth talking about to the all-important TechCrunch. She was going to get all the attention going forward, and IWearYourShirt would get left in the dust (that’s the thought that ran rampant in my mind).

But then, my clouds of self-doubt and anger started to disperse. I felt in a shift in the way I looked at this t-shirt wearing competition that had popped up out of nowhere.

I had to crush Girl In Your Shirt.

(Not literally. I’m a lover, not a fighter, people!)

When competition becomes motivation

Having someone in direct competition with my unique idea created a spark of motivation. I knew I was going to have to work hard to make IWearYourShirt succeed, but now, I was going to turn things up to 11. I was going to give everything I had to my shirt-wearing business to make it more successful and more talked about and to leave any potential competition in the dust.

For the rest of 2008, I obsessively checked in on Girl In Your Shirt. I checked her Twitter and watched her videos, all while putting in maximum effort to do the best work I could possibly do with IWearYourShirt. By the time January 1, 2009, rolled around, I had already sold out 1/2 of my calendar (nearly 200 sponsor spots). Because she’d copied my idea, she had a calendar as well, and I’d sold triple the amount she’d sold.

Competition early on was the motivation I needed to make my business successful, and was probably the most important a-ha moment I’ve ever had.

Competition Proves A Need In The Market

Whether you have a crazy idea like IWearYourShirt, or you’re a designer looking for great clients, or you’re an aspiring food blogger, etc., having other people do what you do proves there’s demand for it.

You have three options if there’s competition in whatever space you’re in:

1. Let the competition crush you: See other people already doing what you want to do, and let them stomp on your dreams until you cry yourself to sleep every night. That sounds fun.

2. See the competition as a learning experience: What can you learn from the people already in your niche? What are they doing that you can do differently? Can you find customers of an existing business like yours and ask questions about what they like and don’t like? Be a sponge, and soak up as much knowledge as you can about what people have already done (or not done).

If someone is already doing what you are trying to do, don’t get discouraged. There are barely any unique ideas left in the world. That’s okay! You can start businesses and embrace ideas that already exist. You just need to put your unique spin on it.

3. See the competition as an advantage: Especially if you’re first in your space, seeing competition pop up is a good thing. It means your idea is attractive to others and is inspiring “me-too” tendencies. When that happens to you, celebrate. I’d always rather be the “I did it first” guy than the “me too” guy. And then, when you’re done celebrating, get back to work. Learn from what the me-too competition is doing and not doing, and keep innovating. It’s a great sales strategy to be able to tell potential customers that you were the first one to start doing X.

Competition won’t go away and why you should be thankful for it

I have my competition to thank for my success. They motivated and pushed me to work harder.

For all the time I spent worrying about her and how she would affect my business, Girl In Your Shirt shut down just a few months after starting. But she wasn’t the only competition I ever had in my t-shirt wearing business. Far from it. As the years went by, there were multiple people who tried to copy IWearYourShirt. I watched as all of them lasted a few days, weeks, and sometimes months. And I kept working hard. Then, as fast as they had appeared, they disappeared into the catacombs of the Internet (somewhere near Geocities, the Netscape browser, and Dogster).

I don’t begrudge them for copying. In fact, I have each and every one of those competitors to thank for my success. Without them, I would have gotten comfortable, and I would have gotten lazy.

Instead, competition kept me on my toes—for that project, and for every project that has come after. Whether it’s an existing idea and someone tried to copy it, or I was starting a project where people had already created something similar.

Don’t be afraid of competition. Embrace it. Be thankful for it. Learn from it, use it to your advantage, and then dominate it!

What’s Holding You Back From Leveling Up In Your Creative Business?

January 16, 2017

Do you feel like there’s just something holding you back from accomplishing your goals, but you’re not sure exactly what it is?

Back in October, some of you will remember that I sent out a long-form survey to get to know you guys better. I wasn’t interested in the typical stuff — how old you were, where you come from, where you found Made Vibrant, etc.

Instead, I wanted to open up a deeper dialogue. Things like — What does success look like to you? What relationship do you want to have between your creativity and your income? What do you think is holding you back?

As I pored over HUNDREDS of entries, I felt l got to know each of you in a much more vulnerable and intimate way. (Thank you for sharing those things with me, by the way.)

Turns out that last question —what do you think is holding you back? —was quite illuminating. 

I was struck by just how diverse and specific the answers were regarding the limiting beliefs and mindsets that keep us from our full potential. With every new entry, I felt I unearthed another fear that I myself had experienced, but that I hadn’t specifically identified for some time.

Which got me thinking…

It’s impossible to break through your limiting beliefs if you can’t first identify exactly what’s holding you back.

So that’s what I want to attempt to do in this article. I went through all your responses looking for patterns and I plucked out 27 distinct mindsets or limiting beliefs that you all feel are holding you back in one way or another.

I want to encourage those of you that feel a sense of potential for your life beyond what you’re experiencing right now to carefully cull the list and write down which of them apply to you.

I’ve also shared some links to past articles related to some of these mindsets so if they call out to you, you’ll have some actionable advice on how to work past them. (You guys know me… I can’t just leave ya hangin’ with a list of things holding you back without some direction on how to change them!)

So, let’s start here, and let’s get honest about what habits and old mindsets have been deepening their grooves in your head.

Let’s identify exactly what’s been holding you back from the future you envision for yourself.

(One caveat: some of these obviously overlap and share similarities, but I wanted to break them out into their most granular characteristics so that we can really see how broad the idea of Fear is and how it manifests in so many different ways.)

1. Lack of Self-Worth

“I don’t deserve good things.”

I listed this first because it is probably the most insidious of all the following self-limiting beliefs. If we don’t believe we’re deserving, we’re always going to be sabotaging the good things that unfold in our lives. This is work that takes time to break through, but once you truly believe you are enough and that you are deserving, it makes the rest of this list become a heck of a lot easier!

2. Lack of Confidence

“My skills aren’t good enough or I’m not unique enough to make my work valuable.”

See this article: Confidence And Learning To Trust Yourself

3. Financial Anxiety 

“I hate looking at or dealing with all things money-related so I just hide from my accounts and hope things get better.”

See this article: How I Wiped Out $7,500 in Credit Card Debt in Six Months

4. Lack of Motivation

“I don’t feel enough of a catalyst to work towards my goals; I say I want things, but I struggle to take action to make them happen.”

See this article: Is There A Secret To Sustained Motivation?

5. Overwhelm

“I have no idea where to start or what to work on.”

See this article: Using Prioritization To Make Values-Based Decisions

6. Guilt of Success

“I’m holding myself back for fear of alienating a family member or partner.”

7. Fear of Public Failure

“I’m afraid if I try things and fail, everyone will see me negatively.”

See this article: The First Helpful Thing Failure Teaches Us

8. Fear of Success

“I’m afraid that if I accomplish my big dreams I won’t be ready for it or I’ll have to sacrifice too much to get there.”

9. Perfectionism

“My skills aren’t where I want them to be and my work is never close enough to perfect so I don’t put anything out there.”

“An imperfect reality will always beat a perfect mirage.”

10. Fear of the Unknown

“I keep myself limited because it’s comfortable and a lot less scarier than putting myself out there and not knowing what will happen.”

See this article: Are Your What Ifs Helping Or Hurting You?

11. Fear of Commitment

“I’m afraid that if I go down one path I’ll be stuck doing that forever and I won’t be able to change my mind.”

See this article: Are You Giving Yourself Permission To Evolve?

12. Lack of Discipline

“I can’t get myself to sit down and put in the work or stick to a consistent schedule.”

See this article: Why It’s Harder For Some People To Form New Habits

13. Self-Sacrifice Syndrome

“I feel responsible for everyone else (my family, my partner, my kids) so I put myself and my dreams last.”

See this article: Re-defining What It Means To Be Selfish

14. Fear of Rejection

“I don’t want to go after projects that I want because I hate the feeling I get when people say NO.”

See this article: How To Deal With The Pain of Rejection

15. Fear of Asking for Help

“I’m at max capacity and I know I need help in order to move forward but I don’t want to feel like a burden and I have trouble delegating.”

See this article: Why Is It So Hard For Us To Ask For Help?

16. Lack of Patience

“I want to see the results of my hard work right away so when I don’t see something payoff immediately, I quit.”

“Give it time.”

17. Second-Guessing Everything

“I’m afraid to make a move one way or another for fear I’ll make a ‘wrong’ move, so I waffle on everything and stay stuck.”

See this article: Are You Afraid of Running Your Business The Wrong Way?

18. Over-Optimization Syndrome

“I need to know the BEST, MOST EFFICIENT, MOST EVERYTHING way to do something or it’s not worth doing at all.”

See this article: How To Make Big Choices With Less Stress?

19. Need for Comfort

“I’m afraid to make any financial investments in my business or myself because I’m comfortable with the life I have right now.”

20. Need for Struggle

“I tend to not trust things that come easily or that just flow.”

21. Fear of Selling

“If I try to promote my work or earn money with my creativity, I feel it undermines the authenticity of the work.”

See this article: Selling What Is True Over Selling What Is Easy

22. Fear of Judgment

“I care too much about what people think about me and it prevents me from doing anything that feels risky or vulnerable.”

23. Lack of Self-Trust

“I can sense my intuition sometimes and what my ‘gut’ wants me to do, but I don’t necessarily trust it; it doesn’t feel practical.”

Watch the workshop: Connecting With Your Core

24. Lack of Focus

“I have SO many ideas that I end up making a tiny bit of progress on each one but never finishing.”

See this article: Framing Your Year With Thoughtful Reduction

25. Lack of Expertise

“I feel like I’m good at a lot of different things but not great at any one thing.”

See this article: How Do I Create A Brand When I Have Many Different Interests?

26. Fear of Disappointing People

“My family or people I care about expect something different from me and I don’t want to let them down.”

See this article: Do You Feel Pressure To Make Everyone Around You Comfortable?

27. Inflexible Idealism

“Everything I work on at all times must be 100% in line with the vision and values I have for what I want to do and who I want to work with.”

See this article: Defining The Relationship Between What You Love & What Makes You Money

One you won’t see on the list “Lack of Time.” Time is simply about prioritization so if you don’t “have the time” it’s because you’re not “making the time” and that means something else is filling up your days. The answer to why those activities are getting all of your attention is hidden in one of the items listed above.

Your challenge this week is to identify which fears/beliefs/mindsets from the list above describe the challenges that are specifically holding you back your own personal evolution.

You can see just based on the fact that I’ve written articles pertaining to a majority of these topics that they are all things that have crept up on me at one time or another. Thankfully, though, by confronting them head on and taking steps to overcome them, I’ve been able to stretch my own boundaries and continually raise my own expectations for what’s possible in my life.

I’m hoping this list is the beginning of that process for some of you!

People Won’t Know What You’re Capable Of Unless You Show Them

December 12, 2016

It’s no secret that possibly the biggest thing that holds so many of us back from making or creating at all is a desire for perfectionism.

We all want our work to be high-quality and fully-formed right out the gate, right? It’s only natural.

Thankfully, though, over the past few years, I’ve seen a shift in conversation encouraging creatives to overcome this barrier of perfectionism. This conversation has given birth to ubiquitous mantras like: “Done is better than perfect,” “Aim for progress, not perfection” and “Start before you’re ready” — all of which is advice I can certainly get behind.

Personally speaking, perfectionism is actually something deeply rooted in my consciousness, being the over-achieving, academic kid that I was growing up. For the past six years, I’ve worked to overcome this mental barrier nearly every day, trying to create and share my work despite the voice in my head that naturally likes to point out every flaw or short-coming or opportunity for improvement.

Today I want to share with you one specific mental shift that helped me start to make that journey from perfectionism-induced paralysis to prolific production (holy P’s!)and it may just be one take that you hadn’t yet thought of.

It starts with a story.

My first job out of college was at an advertising agency in North Carolina. The office was in an old renovated tobacco factory, with industrial-chic brick walls and polished concrete floors. There was ping pong and shuffleboard, dry erase marker frenzied across glass walls, and a coffee bar at the center of the office to work and hang out with fellow co-workers. It was the epitome of what I imagined was a “cool place to work,” and I couldn’t believe I’d snagged such a coveted spot.

But there was a problem — I was so eager to get my foot in the door of the advertising industry and this “cool firm” that I ignored the fact that the only position they had available when I graduated was in the media department.

In short, this meant I spent my days formatting spreadsheets, running banner ad campaigns, and fielding calls from media reps at niche financial magazines. (You see where I’m going with this, right?)

With every passing day, I could feel the walls closing in on the creative essence that I now know to be at my core.

I’d gaze longingly at the creative department that sat in the pod of desks nearby. I’d see them revising logo concepts and brainstorming wild campaigns and editing TV spots. I wanted so desperately to be there with them. Knowing inside the kind of creativity I was capable of and realizing that nobody else knew the potential inside of me inflicted on my heart a slow, desperate kind of suffering that’s hard to describe.

I would daydream about someone from the department marching over to my desk and asking little 22-year-old me: “Hey Caroline, I know you’re super creative and we could use a little extra brain power over here — can you come help us?!” It took me months to actually snap out of my delusion and realize: that is NEVER going to happen.

Why? Because I hadn’t given them any reason to.

No one will know what you’re capable of unless you SHOW them.

“No one will know what you’re capable of unless you SHOW them.”

That’s the simple truth.

In an interview I watched recently, Glennon Doyle said this when talking about the feeling of envy:

“There’s nothing more painful than seeing someone else do something that you feel like you were meant to do.”

We’ve all had that feeling, right? You come across something another person had made and it HURTS. You don’t want it to feel that way but you can’t stop it; the envy creeps in. When that hot feeling of envy rises up in us, it’s usually because we’re actually mad at ourselves for not acting on the potential that we know is within us. We don’t want to feel the disappointment in ourselves, so we pass it off onto another person in the form of envy or jealousy.

Back in 2011, I was itching to start my own blog. I had SO much I wanted to say and share and create, but I couldn’t settle on a name and I had no idea how to customize my blogger template and I didn’t know exactly what I wanted to write about… so I just waited.

I waited for A YEAR. I waited until I finally paid attention to that hot envy I felt when I stumbled upon every favorite blog I saw, and I decided that it was time I stopped whispering to myself “I can do that” and I started proving it by putting in the work.

Again: No one will know what you’re capable of unless you SHOW them.

Don’t just expect people to sense that you’re a writer; start a blog or self-publish a book so you can show them.

Don’t just expect people to guess that you’re an artist; post those paintings on Instagram and show them.

Don’t just expect people to assume you’re musically gifted; publish those tracks to SoundCloud and show them.

Right now you might see sharing your work as scary, especially if you feel it’s not perfect. (Reminder: no one’s is.) You don’t yet have that perfectly cohesive Instagram feed or every page of your blog beautifully designed or each lyric of your song in its poignant beauty.

That’s okay.

Look at sharing your creativity less as evidence of your magnum opus and more as the first line on your resume showing others what your potential is.

With every new piece of art that you make and share, it’s like one more little beacon of proof showing the world (and, more importantly, yourself) what you’re capable of.

I guarantee you, if you simply BEGIN and you share consistently for just one month, you’ll start to experience the thrill of taking what is inside you that’s begging to be expressed, and letting it see the light. That is the soul’s ultimate feeling of freedom, and it’s better than any drug. (Full disclosure: I don’t like drugs, so that’s an easy comparison for me.)

The truth is:

Imperfect freedom tastes so much better than perfect confinement.
Imperfect reality feels so much better than perfect fantasy. (Because it’s real.)
Imperfect progress is so much more satisfying than perfect stagnation.

Your challenge this week is to identify what potential is inside you that you’ve yet to share.

What are you capable of that you can start SHOWING today. Then, make that plan and simply begin.

The tools that are available to us as creators have never been more accessible or more plentiful. Get out there and use them.


I Don’t Have It All Together

November 13, 2016

I don’t have it all together. I don’t know what I’m doing. I have no idea what the next few months/years hold for me. But I’m okay with this.

There’s beauty in uncertainty. There’s intrigue in not having a perfect plan.

With ambition and hard work, you don’t need to know everything.

The 10 years I’ve been an entrepreneur are proof of this. I’ve almost never known where I was going next, or what the 3-5 year plan looked like (heck, what about a 6-month plan?).

I often find myself dreaming of owning a simpler business. A business where I have one product to sell that speaks directly to one customer. But then I think about the limitations that “dream” would bring. The box that “dream” would put me in creatively and operationally. It is much safer to run a business with a single, focused product, targeting a specific customer. But I choose not to play it safe.

I’ve never wanted to play by the rules

I’ve never wanted to play it safe. I’ve never wanted to accept things as they are. This is who I am, and this is what brings me personal fulfillment.

I’ve been a 7-figure business owner, but I can tell you it didn’t mean I had everything together. At every level of business, money does not mean you know what you’re doing or have it all figured out. It just means you’re doing something that people are paying attention to (and paying money to).

I’m okay with not making nearly as much money as other entrepreneurs. I’m okay with not having huge amounts of money in my savings account. Focusing only on money has only led me to dark and unhappy places.

I look at my many businesses as canvases. The ideas for those business are the brushes and paints. Sometimes I paint wildly, ending up with a business that only suits my needs and costs me money to keep afloat (Bumpsale). Sometimes I paint by the numbers, which leads to a business that provides more consistent (but not super sexy) income (Teachery). I’ve come to learn that a mix of both balances everything out.

I’m not in the pursuit of having it all together.

I’m not searching for a perfect idea or perfect business. I’m not sure I’ll ever find a truly sustainable business model for myself. But that’s okay.

As my wife Caroline and I like to say: Life is an experiment.

I’m excited to keep playing this game at my own pace and by my own rules, because that’s what gives me satisfaction.

If you feel the same way, then keep trying things. Keep building things. Keep swinging wildly with your paints and brushes. Enjoy the outcomes, whatever they may be, and know you can always start a completely new canvas at a moment’s notice.