This is no small feat for us. I’ve been hinting at this project here and there, including a mention in my State of the Union at the beginning of this year. This is the business baby my wife and I are having together (sorry folks, human babies are a bit further down the line).
Note: This post will be updated weekly, so feel free to check back for updates in the “WEEKS” section below.
The journey to combine our three business ventures into one has officially started. And of course, we’re being complete weirdos and sharing EVERY DETAIL. If you want to get daily emails and see all the nitty-gritty details we’ll be undertaking, you can click here to get daily updates.
You may be wondering why I’m making a big deal about this transition. Isn’t it easy to spin up an online business?
That’s why we’re going to share all the details on our Under Construction Wandering Aimfully website.
Here’s a bit more of exactly what we’re going to be doing and sharing (I’ll be updating this weekly):
WEEK #1 : BRANDING
We have a business name, Wandering Aimfully, but what the heck does it mean? What does it do? Who does it serve? What does it look like? All those questions and much more were be answered.
WEEK #2: THE BUSINESS
We aren’t writing a business plan in the conventional sense, but we are planning out the business. What are we selling? How much will we charge? What happens to existing customers? How are we working together as a husband and wife team? Read more here.
WEEK #3: WEBSITE
We’ll have a standard consumer-facing website, like anyone else (with an about page, blog articles, etc), but we’re also building a kickass customer experience like no-other. We definitely didn’t finish all the designs by the end of this week, but we made huge progress.
WEEK #4: CONTENT STRATEGY
Articles? Social media? YouTube videos? A podcast? Where does it all fit in? What happens to all our existing content? Read about our intentional approach to creating meaningful content (and not being on ALL the social media sites).
WEEK #5: MARKETING
We’re using an open and closed launch strategy to sell our monthly memberships. But, we also decided to take pre-orders. Get caught up on that.
WEEK #6: WE TOOK A BREAK
While we took a break to go on family vacation, our developers didn’t. They were hard work turning our designs into a reality. When we got back into word mode, we shared some of the biggest challenges we’re facing.
WEEK #7: ODDS AND ENDS + CONTENT
This week was the start of migrating our content from JasonDoesStuff, Made Vibrant, and BuyOurFuture into our new Wandering Aimfully WordPress site. I say “the start” because we didn’t get very far.
WEEK #8 – WEEK #???: CURRENT WEEK…
We have some updating to do… hah.
This will be no small undertaking. In fact, we’ve already been working on it, planning, and ideating for months. But we want to pull back all the curtains and share as much as our sanity will allow.
The under construction site for Wandering Aimfully won’t have much to it the first few days, but very quickly it’s going to fill up with daily posts, weekly videos (sometimes with completely unedited planning meetings we’ve had), and hopefully a bunch of fun peppered in!
The good thing is, I won’t be changing at all. Hah. My action-taking focused content will continue with Wandering Aimfully, but this site and my weekly email newsletter will go away completely (ahhhhh!). We worked that out and talked more about it in Week #4!
If you’re an Action Army email subscriber, here’s what you can expect to get in your inbox the next few weeks:
The fun thing, and what I’m really excited about, is that Wandering Aimfully means so much more than “JasonDoesStuff” ever did.
I can guarantee we’ll mess a few things up along the way, but I’m hopeful you’ll enjoy seeing how we deal with those inevitable bumps in the road.
One of the toughest questions I’ve wrestled with during my time as an entrepreneur is: should I be a specialist and focus on one thing, or be a generalist and explore multiple interests?
You may be struggling with the same question. Trying to figure out what your “niche” is, or whether you’re better suited to working on lots of different things.
I believe I’ve found the answer to our question, and it has to do with money. That precious thing that gives our businesses oxygen. That commodity required to feel a sense of freedom in our lives. Good or bad, money makes the world go round, and it’s the simplest answer to the specialize/generalize question I’ve discovered.
If your goal is to make money and be profitable as quickly as possible, specializing is the absolute best option. Pick one thing to focus on. Solve a very specific problem for someone (or yourself). This will help you build a business quickly and efficiently.
Remember one important thing about building and running a business: A business is the exchange of goods or services for money.
There must be something you are giving someone in exchange for money to qualify as a business and to have any chance of sustainability.
Within the next few days/weeks, you can make money…
1. Selling your time (aka freelance design, development, photography, videography, etc)
2. As a 1-on-1 consultant or coach
Within the next 90 days, you can make money…
3. Building a software application (also known as SaaS)
4. Creating a mobile app
5. Offering in-depth educational content (online courses, workshops, etc)
Those lists could go on and on, but the key here is to keep things simple and focused. The simpler you keep things, especially in the early stages of business, the easier your life will be and the quicker you’ll make money.
Specializing gives you a clear path to hone a specific skill. Some folks call this your “zone of genius.” Be bullish on mastering that zone. Don’t let anything distract you.
Step 1 (First Day) – Buy the best camera and lens(es) you can afford. If you have no budget for new gear, use what you have (an old camera gathering dust in the drawer, your dad’s camera, or even your phone camera), and move to Step 2.
Step 2 (First Week) – Give yourself one week to consume as much knowledge about your camera and the craft of photography as you can. Watch YouTube videos. Read in-depth articles about composition. Take an online course about running a freelance photography business. Be a sponge. But finish being a sponge after the first week.
Step 3 (First Month) – Use the hell out of your camera for one month. Shoot every event and situation you can. Take 500-1,000 photos per day. Delete them all. Shoot. Delete. Shoot. Delete. Build up your resistance to taking the perfect photo, and just learn your gear and hone your photography skills.
Step 4 (Second Month) – Spend one month doing unpaid photography work for friends. Headshots. Weddings (even if they have a “professional” photographer, ask to tag along). Corporate shoots. This could be done in conjunction with Step 3.
Step 5 (Second Month) – Build a super simple website. I’d recommend using a template from Squarespace. Give yourself one weekend to put your site together. On the homepage of the website highlight the type of photography you want to focus on (weddings, corporate, etc). Showcase your work based on that focus*. Give someone a way to pay you for an hour of photography (or at least contact you for bookings. Gumroad.com is a great option). Make a list of 25-50 friends, and email them your photography website. Ask them to share it with anyone they know who might need your services.
*Remember: We’re specializing here so we can get to money-making as quickly as possible.
Step 6 (Third Month+) – Search local event guides, reach out to small businesses, or scour craigslist for happenings in your city that might require an official photographer. Call the decision makers and pitch yourself and your services. Keep shooting. Keep getting better. Keep trying to find your unique photography style. Kick serious ass and over deliver so that these local event folks want to share you with their friends.
I guarantee if you followed those six steps you would build a profitable photography business in just three months. Sure, you may only be making $500-$1000 in your first month, but that’s more than $0. And once you start making money and landing clients, more opportunities will come your way.
In 2013 I set out to reinvent myself and my business. I gave myself a two-year window to be a generalist and consistently experiment. In those two years, I had a very broad focus (and still do!). By being willing to create all kinds of things, and in my own way, doors opened.
Sometimes the door of your business is barely cracked. Sometimes the door of your business is wide open. But either way, the door isn’t shut!
Being a generalist and not having a singular focus will lead you down many paths. 90% of those paths help you learn what you don’t want to do.
It’s often more important, in the long run of running and owning a business, to figure out all the things you don’t want to do be doing.
You don’t learn and grow from success. Where the learning and true growth happens is when you screw up and when things go bad.
Just like the specialist lists above, this one could go on, but the secret to success here is to avoid becoming too narrowly focused. Don’t get too specific about what you’re doing or where you’re going. Stay open to possibilities, take care to notice the doors that open as you do so, and decide on the fly whether to walk through them.
Being a generalist keeps your options open and lets you develop some competency in a variety of skills. You’ll harness distractions as opportunities to discover and pursue something cool.
I’m not advocating that you become either a generalist or a specialist. That choice is up to you, but I think the question of when you need money helps to make the decision simpler.
Need money now? Specialize. Pick one skill and GO.
Have time? Generalize. Enjoy the ride and soak up all the experiences.
I started my first blog back in 2011.
May 18, 2011 to be exact. How do I know this? Well my first post still exists. You can read it here. (But not yet! You have a whole email to get through first before I lose you to the time machine/rabbit hole known as the internet. SO keep reading then you can satisfy your curiosity by seeing what the 2011 version of me found so interesting to write about…)
Back when I started this first blog, I had just ONE intention: get the thoughts and ideas swirling in my head out and “on paper.” I felt like I had things to say and every day that went by without saying them felt like a waste of creative potential.
My own self-doubt was my greatest challenge, so just hitting ‘publish’ on a post was a HUGE win for me. The more posts I published, the less fearful I felt. The more confidence I gained.
Once I got a handle on my doubt and cultivated the self-discipline to sit down and actually write, my One Intention evolved.
I actually want people to read this, I thought. So I shared links to my blog posts on Facebook with my friends. And on Twitter with people following me. And people started to read my posts and share them. I started to build a tiny audience of people who cared about what I was making and what I had to say.
For the next three years, it didn’t even occur to me to try and turn this creative outlet into a business. I let pure passion and curiosity direct my time and attention. I taught myself design and Photoshop. I honed my voice and my writing skills. I learned how to stick to a content schedule and to get over my perfectionism. I figured out what I believed in.
All of these things turned out to be essential in building a strong foundation for the creative business that would evolve from it all by 2014 when Made Vibrant was born. That’s when my One Intention became finding a way to turn my creative expression into something of value for others, something my small audience of people might pay me for.
Now… why am I sharing all of this with you and taking you down Made Vibrant Memory Lane?
It’s actually to illustrate a point that I think could help SO many of you out there, especially those of you still searching for a way to turn your skills and passions into a business. It starts with this advice:
I know you’re probably searching for the blog posts or the online programs or courses that are going to give you that one magical shortcut — the thing that is going to take you from no audience to a paying audience like yesterday. And it’s only natural for you to want that, especially with how many more resources there are now online about how to start your business.
Trust me when I say this, though:
Searching for a shortcut is actually just distracting you from the one tactic guaranteed to be effective: putting in the TIME.
Every day and month and, yes, YEAR that goes by while you try to plan out the perfect strategy, that is all time that you could have spent actually making something, which is the foundation for any profitable creative business. Time you could have spent honing your voice and your skills. Time spent figuring out what YOU believe in.
It’s all too tempting to focus on the big, complex, well-oiled machine thing right out of the gate. You want the polished brand, the booming blog, the online products bringing you passive income, the adoring audience with thumbs and hearts and comments at the ready, the segmented content based on interests, the podcast interview requests, the book deal and the sponsored travel.
If this is what you’re chasing down though, it’s likely that you’re going to find yourself with a lot of half-baked ideas, more spinning plates than you can handle, and a lot of unmet expectations.
Instead, I recommend doing what my 2011-self did. Begin with ONE intention: to get your ideas out of your head.
Hone your message. Develop your confidence. Figure out what you want to say. Better yet, figure out HOW you want to say it by going within to understand who you are and what makes your perspective on the world one-of-a-kind.
To put it simply: focus on the foundation first.
All big, beautiful trees must begin with a seed, right? This seed may be a simple beginning, but it is powerful with potential. From it, a network of strong and sturdy roots begins to spread, creating a foundation that will support whatever complex growth this tree might undergo in the future.
If I was starting my business over from the beginning, here’s how I would start simple and layer in the complexity as I grew.
Practice getting those ideas out of your head and into reality. What is your craft? How can you improve it and develop your own unique recognizable style or approach to what you do? Do you enjoy what you do? Would you still do it if no one ever paid you for it? There isn’t a shortcut to making things, so start TODAY. Quit strategizing and start making.
Once you know your intention is pure and your craft is somewhat focused, you’re in the best place to connect with an audience. However, you can’t build an audience of people who value what you do if they can’t see what you do. Create a portfolio. Share your writing. Post your artwork. Take on pro bono work. Whatever you need to do to make your work visible, do that. Stay connected to your audience with a newsletter or through email correspondence — social media changes all the time but email is still the best way to maintain a line of communication with your audience that you control.
AFTER you’ve spent time building an audience and you know you have something that connects, consider ways that someone could pay you in exchange for your skills, services or work. Then… ask. Avoid making assumptions about what people will or won’t pay for. Instead, test those assumptions by making the ask and learning from the results.
It’s entirely possible that you’ll go through several ideas — some winners, some losers — while you figure out a business offering that connects with your audience AND makes you sustainable income. That’s okay. That is the core challenge of being a creative entrepreneur. If you can’t find a way to enjoy that process of trial and error, well it’s possible that owning your own business may not be the right path for you.
Many people make the mistake of trying to over-optimize before they have any sustainable revenue streams, and this is what leaves them completely overwhelmed and exhausted. (I’ve been guilty of this myself.) It’s probably not all that helpful to distract yourself with automation and list segmenting and marketing to new audiences if you don’t even have a product or service offering that is working yet. Remember, focus on the foundation BEFORE you add unnecessary complexity to your business. That is the key to not completely burning out before you land on something that works.
I know we all want to skip ahead to “the good part.” The part where it’s all working smoothly, we’re making a sustainable living, and we get to spend our days creating and doing what we love.
But trust me, for the sake of your creativity and your sanity, begin with the roots and THEN branch out as you go, when it makes sense.
If you give yourself permission to block out the branches for now, to focus on the foundation—planting the seed or strengthening the roots—you may finally get that “shortcut” you’ve been hunting for in the form of some good old-fashioned hard work.
I’d made well over $13 before 2008. In fact, I had a perfectly acceptable 9-5 job that paid me thousands of dollars per month (as many of you reading this probably do). But on one morning in 2008, I made $13 and for the first time in my life experienced making money completely on my own. Someone random on the Internet paid me money for an idea I had.
I’d made every single dollar, until 2008, in “normal” ways. I did chores as a kid and had an allowance (it was measly, but aren’t all allowances supposed to be that way?). I had a handful of “normal” jobs growing up:
I share all of these jobs with you to point out that it was always a standard payment for services rendered. Normal jobs, if you will.
In 2008, I got my first taste of entrepreneurial money. That sweet, sweet nectar that I became addicted to and would continue to chase (and still do, but in a healthy way). My IWearYourShirt business had just launched to crickets (and they didn’t have money, those cheap-insect-jerks), and I started emailing friends and family to share my website with them. This was both in a moment of panic, but also because I had a thought: “If I don’t tell people about this idea, how in the world do I expect them to find it?”
Don’t be afraid to share your ideas. If you’re proud of what you’ve created, share it!
Those few emails to friends and family weren’t sales pitches. They were just friendly hellos, accompanied by a request to check out or share this crazy t-shirt wearing scheme (err, business) I had come up with. Unbeknownst to me, a few of the email recipients took pity on me and deposited money into my PayPal account via the fancy buttons on the website link I’d sent them.
Brace yourself: After the first day of sending emails, I’d made $13.
I’ll give you a moment to pick yourself up off the floor. Are you okay? You are? Great. Things get a little bit more exciting from here.
That $13 increased to $500. Then $1,000. Then, after two and a half months of emails and tweets, I was looking at a PayPal balance containing over $6,000.
I’m going to steal this wonderful sentiment from my wife, Caroline. Mostly because she’s the better writer of the two of us, and because… joint household (see, babe? If I win, we both win!)
Anyone can get paid. Anyone can get a job. Anyone can exchange time for money. But it’s another ball of wax (why is it a ball of wax? who even has ever owned a ball of wax?) to make money.
When my IWearYourShirt business started making money, I noticed a shift in my thinking. Sure, I’d read about and seen other people who were making money from their ideas, but I had never done it. I had never had that experience.
That first $13 was like seeing the light. It opened my eyes to this idea that you literally can do anything and make money from it.
If getting paid to wear t-shirts isn’t proof of that, I don’t know what is. The feeling you get when someone gives you money for your thoughts is unlike any other. Many successful people, or at least experienced entrepreneurs, will tell you that the money itself pales in comparison to the transaction that happens. Someone is essentially voting for you, saying YES to you, with their dollars. If you haven’t felt this feeling before, I will warn you: Once you feel it, you won’t want to stop feeling it.
This little eight-word phrase has become a mantra for me. It works well in life, but it works especially well in business. Any time I have an idea and self-doubt starts to creep in, I simply combat that self-doubt with the broadsword of asking. It’s not a physical broadsword, although that would be really cool. But it is a metaphorical-weapon I keep in my arsenal.
Self-doubt will say, “You’re an idiot! no one will pay for this! Hahahahaha, you’re also ugly!”
(We all know self-doubt is also a name-calling a-hole.)
My broadsword of asking will reply, “You may be right, self-doubt, but we won’t know until we ask, right?”
Then self-doubt retorts, “You’re still ugly!”
It’s silly, especially imagining self doubt and a broadsword arguing, but we all deal with it. We all have some version of these thoughts. But if I’ve learned one important thing since making my first $13, it’s this:
The rejection you receive from asking also gets easier over time, because you know you’ll have something more interesting to ask for again in the future.
This eight-word mantra, “You don’t get what you don’t ask for,” has popped up time and time again since that initial day in 2008. I continue to refer back to my broadsword of asking. I continue to make money, not only because I have ideas and execute them, but also because I’m unafraid of the consequences of asking.
How about that for a sweet alliteration? It’s also the truth. If you can land ONE sale, you’ll feel a sense of empowerment that can fuel you to continue. But without that one sale, you can feel powerless.
So, is it that simple? You just have to make your first sale?
I’d say: YES.
Sure, you aren’t going to retire rich, pay off all your debt, and buy that gold-plated yacht you’ve been dreaming about with just one sale. But it will give you something you can’t manufacture: momentum. And with momentum, you can push through and more easily combat your thoughts of self-doubt.
If you’ve already made your first sale, awesome. Relish that. Enjoy it. Learn everything you can from it so you can make your next sale. And then your next. And then your next.
I hope you make way more than $13 from whatever you’re working on, but don’t lose sight of the fact that everyone starts with a version of this story. And everyone remembers their version, no matter if they go on to make $1,000 $100,000 or $100,000,000.
You just have to start.
It was 2011, and I was on stage at Fast Company’s Innovation Uncensored event. I sat in the chair where Gary Vaynerchuk was supposed to be. Gary was the guest for this particular panel but his flight got delayed so the folks at Fast Company asked me if I’d be willing to slide up and fill his spot. You can imagine the audience’s disappointment, right?
On the spot, the moderator asked me what my definition of innovation was, and without giving it too much of a thought, I responded:
I only remember this so vividly because it’s the same definition my wife still uses to this day (and repeats back to me in an effort to point out my occasional overuse of the word “awesome.”)
Now here’s why I think this definition matters, and especially why it might matter to you if you’ve had an idea brewing in your head for a while now but have yet to turn it into a reality…
Whether you have an idea that feels like it’s been done 100 times or whether you have an idea that feels so far-fetched it could only work on Elon Musk’s Mars, YOU are more than capable of innovation.
Let me explain.
Chances are, if you have an idea and you haven’t turned it into a reality yet, it fits into one of these two categories:
This is the category that most of my own projects have fallen under over the years. Whether it was getting paid to wear t-shirts for a living with my company IWearYourShirt back in 2009 (I donned t-shirts with logos and made YouTube videos before “YouTuber” was a widely accepted occupation); or selling my last name twice (auctioned off my last name for $45,500 to become Jason Headsetsdotcom in 2013 and again for $50,000 to become Jason Surfrapp in 2014); or making $75,000 on my first book, Creativity For Sale, by selling sponsorships at the bottom of every page (before I had written a single word of the book); for a while there, I had the market cornered on “business ideas that will make people laugh in your face.”
With every single one of these ideas, I asked my friends or family or close business peers what they thought, and with every single one, the majority of those people doubted I could make any money at all.
That’s the trouble with Category 1 ideas…
What hasn’t been done before (aka “where awesome is not”) is made up of equal parts endless possibility and raging disbelief.
But then, of course, you have Category 2.
Let’s take a second to talk about ideas “that have been done already,” shall we?
In 1996, two smart guys started working on a project together out of their garage. While this project was unique to them, and they were going to put their own twist on it, there were many other companies who had already created businesses in their specific niche – twelve of them in fact, a handful of which had become extremely popular and profitable.
But these two guys believed in themselves and saw an opportunity to do things differently. They knew they could add their own unique twist on an existing idea.
Maybe you already know that the guys I’m talking about are Larry Page and Sergey Brin, the founders of Google. But maybe you didn’t know that 12* other companies had already created search engines (many of them doing extremely well) before the idea for Google came to be.
In both idea-categories I mentioned, you have a tremendous opportunity to make awesome where awesome is not in this world.
Your opportunity for innovation gets taken away by never doing anything at all.
Innovation doesn’t just have to mean that you invent the technology that revolutionizes communication. It can also mean that you simply make something that didn’t exist before.
It could be that you find a way to monetize platforms that already exist like I did (in spite of those that don’t believe it can be done.) It could be that your version of “making awesome” isn’t necessarily in the what you make but in the how you make it, like Larry and Sergey figured out a way to do search in a way it hadn’t been done.
Whatever kind of idea you have though, the only way that your opportunity for innovation gets taken away is by never doing anything at all. By standing still. By letting that fear get the better of you.
Here are the three things that have made the biggest difference for me in getting my ideas off the ground.
You could be building the next Instagram. You could be creating an online course. You could be writing your own book. You could be trying to get paid to wear t-shirts for a living.
No matter what you’re creating, if you don’t believe in yourself and your idea first, you’ll never reach any level of success.
Thankfully for me, this is a trait that I was born with. For as long as I can remember, even as a little kid sitting in a bedroom dreaming up ideas for comic book characters, I always looked at the world differently. There were times in my childhood when it became clear that doing things differently wasn’t the way to get ahead, especially in school. I was starting to pick up the fact that maybe being “smart” was a better way to navigate than being “different.” Boy am I glad I didn’t let those voices get to me because as it turns out, being smart isn’t the only thing that counts. Scoring well on tests isn’t the only thing that counts.
As long as you carry an unwavering belief in yourself and trust your gut when navigating those deep, dark, and uncertain waters of creating something unique or something that hasn’t been created before then you also have the power to help people see your vision of the world and what could be.
Every idea I’ve ever had has had one thing in common: I wanted to get XYZ thing, more than I feared what it took to get it.
That’s what sets people who make ideas happen apart from people who don’t, and that’s the very first reason any of my ideas go from thoughts swirling around in my head to viable businesses that create value and generate revenue.
Until you make an ask, your idea is nothing more than a cartoon bird floating around in your mind. (And unfortunately, you can’t pay for lattes or your rent with cartoon birds in your mind.)
Ironically, being willing to make the ask is also what can help you overcome the self-doubt. The fear of the unknown is crippling: Will people hate my idea? Will they laugh at me?
Once you realize hearing “no” isn’t as bad as you thought (and it never is), you gain the ability to keep asking until you hear a “yes.” And let me tell you, all you need is one “yes” to stoke the flames of your own belief.
Your friends. Your customers. Your clients. Your shareholders. They’re not going to show up on your doorstep and throw yeses at you because you read this article or any other article on entrepreneurship, business, etc. But they will show up if you believe in yourself and you ask them to show up. It may not happen the first time. You may have to ask more times than you’re comfortable asking. You may have to modify your ask and change up who you’re asking, but if you want to achieve your dream more than you fear the reality to takes to get you there, your ask(s) will be rewarded.
Everyone wants happy customers with glowing testimonials to put on their websites or the back of their books right out of the gate, but it takes time to gain an appreciation for your ideas.
Imagine that the gaping void of validation that you crave for your idea is in the shape of a bucket. A bucket of appreciation. The mistake most people make is forgetting to look at their buckets of appreciation in relation to where they are on their journey.
The day I launched IWearYourShirt, 12 people showed up to the website (and I’m pretty sure 5 of those were my Grama.) If I had been expecting a response that would fill a Grand Canyon-sized bucket of appreciation, I probably would have given up and shut the whole thing down that very day. I had the ability to see that I was just at the very beginning of the life of my idea, and those 12 people were enough to feel appreciated in a bucket the size of which matched the age of my idea.
Google didn’t start out as one of the most profitable companies in the world. They started out with a $100,000 check from their first investor (and a slightly upgraded garage). Sure, you may or may not be chasing $100,000 at the beginning stages of your idea like Google, but the point is that if you don’t appreciate your business or idea at every stage in its existence, you’re quickly going to overwhelm yourself with unrealistic expectations. Your bucket of appreciation will end up feeling too large, and any praise you do get will barely cover the bottom.
It’s important to dream big but also to match your expectations with your reality.
Instead, it’s important to match your expectations with your reality. Dream the big dream of creating the next Google if that’s your aim, but put your expectations in check with what your current circumstances are.
With patience, not only will you find the right people to fill up that bucket of appreciation that you’re so desperate for, but you’ll find that the size of your bucket will grow in proportion to the hard work you’re willing to put into your idea.
These are the ways that I’ve been able to make my own awesome, in my own way, for over a decade now as an entrepreneur, and I’m far from being done.
I wrote this article because I hope you turn your current or next idea into a reality. I hope the cartoon bird version of it flies out of your mind and morphs into a first (actual) version that someone can pay for.
I hope that you stop looking at competition in whatever market you’re in as a hurdle, and instead, see it as proof that people are willing to pay for some version of your idea and as an opportunity to innovate in your own unique way. I hope you believe in yourself and channel that belief into the work it takes to receive the appreciation you’ll get if you make the asks (and then repeat that process over and over again).
I’ve been blown away by the appreciation of my ideas over the years, and I want the exact same thing for you.
I said it as an offhanded comment in 2011 and I’ll say it again:
Let the making begin.
I love Nike’s slogan: Just do it. It’s a great motivator. There are lots of difficult things in life that you should do anyway. But for this article, I want to tell you why you shouldn’t do it.
And what’s “it?” Starting and running your own business.
Are you someone who loves the idea of putting your entire business on autopilot and automating everything? Yeah…first of all, best of luck with that. I know absolutely no one who runs a successful business that is completely automated. But secondly, the effort (read: the journey) should be the fun part. It has to be, actually, because the challenge is going to crush you otherwise. You’re going to work longer and harder than you ever have in your life, and the payoff is so far removed from “overnight success” that everyone who’s ever succeeded in business just laughs at that concept.
If you aren’t ready to invest countless hours and make big sacrifices in your life, you shouldn’t do it.
You can have the most ironclad and well-thought-out business plan of all time. You can have experience from previous businesses. You can have amazing mentors and maybe even a bunch of funding.
But you know what? Your plans will change. If you’re doing it right, your vision will be shaped and molded by what your customers are actually willing to pay for. Your plans will fall apart as quickly as you can say pivot.
If you’re allergic to change, you shouldn’t do it.
You aren’t going to be the next Steve Jobs.
You aren’t going to be the next Elon Musk.
You aren’t going to be the next anyone.
You are going to be you. No one knows who you are, and that’s a really big hurdle in people’s minds. They’re not going to trust someone they don’t know, and it’s a lot of work to get people to both recognize and trust you. It’s an even bigger hurdle to do the work your business requires without the expectation of ever getting accolades for it.
If you’re hoping to see your name or your business’ name in lights someday, you shouldn’t do it.
You are going to make mistakes. You are going to have to make tough decisions, and no one is going to be able to give you all the answers. All the advice in the world can’t help you when YOU have to be the one to make the tough call. And sometimes, you’re going to make the wrong one. It’s going to suck.
If you are afraid of failing often, and in public, you definitely shouldn’t do it.
You shouldn’t start your own business. You should keep your job and make the best of it you can. Enjoy every day of job security that you can soak up. Relish the idea that you know where your paycheck is coming from and that someone else has to make all the tough decisions.
If these things don’t scare you into hiding, then maybe you should do it.
Wait, what? Is that contraction supposed to be there? Shouldn’t that have said your idea is good enough?
If your idea was good enough, you would pursue it. If your idea was good enough, you would carve out precious time for it. If your idea was good enough, it would keep you up at night and force you to work on it, hour after hour.
What I’m saying is that you’re resisting taking action with your idea. The reasons for resisting might be totally legitimate. Sometimes we’re just not ready, and that’s okay. Not being ready is okay.
Sometimes we’re TOO ready, and we get dangerously consumed by an idea. Some people’s ideas take control of their lives.
It can be scary to have an idea so powerful, or a job so demanding, that it ruins relationships and destroys your health.
Sounds drastic, right? How could a simple thing like an idea do that? Ask Mita Diran, the 24-year-old copywriter who died at her desk after spending 30 straight hours in the office. Consider the Japanese concept of karoshi, which translates as “death by overwork” and is estimated to claim 200 workers every year.
That’s not what we’re going for here. I don’t want you to swing from procrastination all the way to dangerous obsession.
The key is to find a comfortably challenging place between procrastination and obsession. A place that will empower you to get things done and still enjoy your life. To take action with your idea.
What’s something you just feel you need to get out into the world? What is something you can’t stop thinking about?
We all have bills to pay, but we all also spend hours wasting time. Watching TV. Reading random articles on the Internet. Reading every book by Seth Godin. Scrolling through social media feed after social media feed. Every single person, myself included, has the extra time to create the thing we can’t stop thinking about.
What people want: To make money doing what they love.
What people don't want: To do the work that it takes.
— Jason Zook (@jasondoesstuff) May 9, 2016
How? You’ll stop having so much time to read articles like this one. You’ll fall behind on your favorite podcast. Heck, you may even miss hitting inbox zero for a few days/weeks.
But when your idea is good enough, it will demand your time. Not all of it, because your idea wants you to have a life, too. But a lot of your time. And when your idea is good enough, the time you invest will be rewarded.
For as long as men and women have walked upright, there has been some sort of commerce. Trading food, pelts, gold, goods for services, etc. Throughout it all, there is one common element that has secretly remained unchanged: there are no rules.
You may think there are rules, but look at our current reality as an example:
Even more interesting (to me, at least) is that I could sell whatever* I want to whomever I want. Used cereal boxes? Yep. A subscription service about the mating habits of chameleons? Sure. Snow? It’s been done. If you can dream it up, you can sell it, and no one can tell you no.
*Of course, I can’t sell drugs or anything that’s illegal. Stay with me here, and try not to poke a hole in this theory just because there are also no rules about criticism.
Another great non-rule about starting a business right now? You could make $100,000 tomorrow. It would be incredibly difficult to do, but the ability for that to happen is 100% possible. 50 years ago? Good luck.
I bet you can count on your fingers and toes the number of people you know who hate their jobs. You might even be one of them.
Why do we resign ourselves to doing work all the time that doesn’t bring us joy and happiness? Why do we subscribe to “rules” that don’t exist about how to work and live?
I’m not trying to paint a picture where everyone in society has a job they love. I know that’s only going to lead to people saying, “Who’s going to clean our toilets?” and “Do you think all the trash men/women have fun disposing of your garbage?” So let’s not go down that road (for now).
Let’s go down the road of making time and space for fun in our work. Time and space for making your own rules.
I don’t mean a corporate trip to Legoland to do team building and synergistic yoga exercises (…everyone get into downward-facing-demand-chain-economic-reporting). I mean allotting time for projects that have no immediate tangible benefit. Doing things that are a bit outlandish and may even veer into bizarre/crazy/what-the-hell-were-we-thinking spectrum.
Amazing discoveries are made when you’re willing to have some fun without limitations (revenue projections, legalese, etc). If every decision you make has to involve the bottom dollar, then I truly feel sorry for the way you run your business.
You know what people talk about? They talk about things being done differently. They talk about the weird things that pique their interest. They talk about memorable things. Not a single person goes and tells their friends about the amazing time they had doing downward-facing dog poses with the accounting team.
Trying to have fun can spur ideas.
Trying to have fun can land you press and attention.
Trying to have fun can do more for personal and team morale than any raise, bonus, or product launch.
I read an article recently by Ali Mese titled I can’t tell you why your business is growing. There was one point that stuck out for me:
I strongly believe that adding a little fun here and there can (and will) delight your customers. Even if whatever fun thing you create isn’t something they can buy or have.
It’s nearly impossible to measure the ROI of fun. But not everything in business needs a measurable ROI.
Make one day of the work week about exploration and play: Encourage your employees (or just yourself) to spend one day of the work week having fun and creating for the sake of creation.
Fun doesn’t need an ROI. Fun just needs to be fun!
Show and tell goes a long way: My friend Paul Jarvis and I set out to create a silly product in 24-hours called Emojibombs. By most people’s measurement that project was a failure (it didn’t make money and we shut it down fairly quickly thereafter). But, we saw it as a success because we got to engage our audience for a couple days, show them every stop of the process, and people still remember that project.
Build a tool or website that you’d enjoy: Similar to the Emojibombs example, build a tool or website that you’d love. Maybe it’s a how-to guide on DIY’ing your own saddle for corgis? Sounds super silly, but if you love dogs, you may make something that other dog owners would enjoy and share. You could also make something helpful, just remember to keep it fun!
Travel: As obvious as it sounds, there’s so much fun and discovery to be had by getting out of your comfort zone and routines. You don’t have to go somewhere extravagant either, odds are you have something fun and unique to check out just a few miles from where you currently sit.
Films some videos or a podcast: Creating content can be incredibly fun, especially when there are no business objectives behind it. Just create for creation sake and follow one of your passions. Don’t measure anything. Don’t look at the analytics. Just. Have. Fun.
I would imagine most entrepreneurs and business owners don’t have fun for fear of what people will think.
What if I alienate a customer who thinks we don’t take our business seriously?
What if we show that we’re having fun and a big client thinks we just goof off all day?
In our current no-rules-in-business society, you get a badge of honor for working hard and hustling. What if instead of another honor badge, you went for some colorful flair (fun!)?
I’m up for having more fun and not worrying about it increasing my revenue. Are you ready to join me?
At this point in my entrepreneurial career, I have about 30 projects under my belt. Some have been very successful. Some have done just okay. Some have been complete flops. But they all have one thing in common: they started ugly.
You might think that project 29 or 30 started out perfectly, right? With 20+ previous experiences, I had to have figured out how to avoid all the mishaps, errors, and ugliness that go along with a new project.
For the sake of this argument, I’m defining ugly as a version I’d be embarrassed to show a potential customer.
The project I’m going to share with you throughout this article is called ofCourseBooks. A project I previously co-owned with friends Paul Jarvis and Zack Gilbert. The three of us came together with the idea to create elegant embeddable workbooks.
But guess what? Things didn’t start out elegant at all.
Sketches on paper. Really quickly thrown together designs. A bunch of bad ideas tossed in a Trello board. All of these things are necessary when starting a project.
It is 100% impossible to get a project from initial idea to beautiful and ready for the world in a straight, linear fashion. Instead, it looks more like this:
Yeah, it looks like a mess, and yeah, it often feels like things might crash and burn at any moment.
If you accept that this phase of a project is necessary (or even mandatory), you can look at it from a completely different angle. You can embrace the ugly phase, and you can use it to your advantage to create without criticism or judgment.
With ofCourseBooks, we didn’t worry about everything being perfect from the beginning. We just allowed ourselves to create the first version of a logo. The first version of a branding guide. Definitely the first versions of the website framework and design.
And how many iterations did each of those “first versions” end up having?
Paul, Zack, and I all have experience working on previous projects, which helped us understand that things wouldn’t be perfect on the first go-round. We came together as a team and had conversations about letting go of perfectionism, and about our willingness to create new versions of things —without complaining about the extra work.
This is where the word “iteration” actually means something. It’s not just a buzzword, people. It means making changes quickly and without hesitation. It means throwing away hours of work that no longer serve the greater good of a project. It means swallowing your entrepreneurial pride and realizing that no one ever makes anything perfect on the first, second, or even third try. Shifting your thinking in this way can help you reach the next milestone or level of success faster than you’d imagine.
I remember what it was like pining over designs for various projects, or even over words for various articles. It was tedious, nitpicky work. And it wasn’t until I made the big shift in how I defined the success of my art that I began to understand and embrace that my ugly ducklings could quickly become majestic and powerful mallards!
Nowadays, especially with writing, I just sit down and know that the first version doesn’t have to be perfect. There is no perfect, and an ugly duckling is okay. This single thought has completely removed writer’s block from my vocabulary and life.
I learned in 2015 that people don’t need the perfect picture to be interested in buying something.
In 2015, I wrote a daily journal for 60 days on the writing platform Medium. In that journal, I shared my heart, soul, and ugly thoughts about what it took to create my next big project (BuyMyFuture). I was scared to publish many of the daily entries I wrote because they were ugly and vulnerable. One, in particular, was titled, “Does anyone even care?” Here’s an excerpt:
A funny thing happened when I shared my vulnerable and relatable thoughts. People became even more interested in the project.
How interested? Over half of the 165 buyers of BuyMyFuture said they read the Medium journal and that it influenced their buying decision!
(The first year of BuyMyFuture was sold at $1,000 per spot.)
Going back to ofCourseBooks, we shared a public Google Doc with our podcast listeners and email subscribers. In that doc (as you can see), we shared all our ugly versions and a bunch of our thoughts along the way. Remember, our definition of ugly may vary to your definition of ugly.
And surprise, surprise: many of our founding members say they purchased when they did because we shared the behind the scenes (read: ugly versions). They saw the progress and knew we’d continue to improve our next versions of the product.
Say this out loud: “I know this is the ugly phase. I’m 100% okay with making mistakes and having to redo work.” The more you say it, the better the outcome of whatever you’re working on will be.
Whether it’s writing an article, building a piece of software, designing a new logo, or all the other millions of ways you can create things nowadays, be okay with having an ugly duckling phase. Understand how beneficial it is, and shift your mindset from worrying about it to leveraging it in the creation of something even better.
Be okay with starting ugly. It doesn’t last forever, but it’s completely necessary.
I hopped on a Skype call with a guy named Ash to answer questions about content creation. Ash wanted to talk about writing and defining success. During the call, he asked a simple question: “With the content you create, how do you define success? Do you look at analytics, shares, or other data?”
The answer was (and is) no. I don’t look at any of that stuff. I don’t care about the analytics. I’ve been writing for years, and I define success not by numbers and graphs, but by getting an idea, thought, or opinion out into the world and hoping it brings people value. That’s it.
Success happens on the front end of the distribution, not the back end. Hitting publish is success and then it’s on to the next article.
Ash responded, “That’s very interesting. It’s kind of like your writing is your art.”
I’d never really thought of it that way. I’d never thought of the words I write as being anything artistic, or of myself as being an artist. But then I thought about what the word “art” means to me:
I’m not concerned about my writing “doing well.” In fact, some people might argue that only one of the nearly 400 articles I’ve written (thank you, WordPress post counter) has actually been successful by traditional metrics. That article is the weird morning ritual one, and it’s been viewed over 1,000,000 times across multiple media outlets. And while that’s great and all, if I let that article be the measuring stick of my writing success, I’d be fighting a never-ending battle. It’s so rare that an article will spread like that one did, so trying to recreate that with each article would put me in a creation-straight-jacket.
I recently heard about Cherie Northon, an environmental scientist and self-described “non-artist” (like me) who has dedicated her career to showing people how seemingly small things like littering can have long-term effects on the planet. Cherie knows all kinds of stats—like the fact that 80% of the ocean’s plastic garbage comes from the land—but she also knows that many of us have turned a deaf ear to tired messages like, “Don’t litter.” So how could she get people to care and, more importantly, take action?
She turned to art—or, more specifically, to partnering with artists who could communicate what we all already know in a new way. She’s used her credentials to bring legitimacy to art pieces made of ocean garbage, and the artists have used their credentials to ensure the message to use a trash can actually gets heard.
Did Cherie have to become a traditional artist to get her message out there? Nope. She had to redefine art as a way of getting her message out, and then find a way to act without getting caught up in how it would be received. She’s written that “few will probably ever see” a piece that means a lot to her—an albatross mosaic made of plastic found on the beach—but she doesn’t let it stop her. You shouldn’t, either. Find your art, and take action.
I know insanely talented people who get so wound up about putting their work out into the world. Every part of the process is painful for them because they don’t create enough to get over their self-doubts, fears, and imperfections.
When I first started writing, I had to overcome a lot of my own self doubts, fears, and imperfections with a simple idea: That article I just wrote is done, it exists in the world, your time with it is done, it’s time to move on to the next one.
You will always have another thing to design. Another video to create. Another article to write. Remove the pressure of thinking you’re creating the last _______ on Earth, and just get your message out.
The more I create, the more I’m able to create without over analyzing and putting pressure on myself.
If there’s one important thing I’ve learned in the past decade as a creative entrepreneur, it’s that the more I create, the more I’m able to create without over analyzing and putting pressure on myself.
I can now write article after article and not worry for a single second about how each one will do. That’s not my definition of success. If an article makes its way from my writing app to my email list and website, it has succeeded. Done deal. End of story. On to the next article.
1. What is your art? Remember: you don’t have to be an artist to create art, and your art might be something you don’t even realize. In the end, it’s just the vehicle you use to get your thoughts and opinions out into the world.
2. How can you define success for your art that has nothing to do with forces outside of your control? Can you detach from the metrics and find success with your art from another angle?
Look at analytics if you want to, but don’t get caught up in them as your metric for success. They will only feed your anxieties the next time you sit down to create, and you don’t want your self-worth tied up in algorithms. Remember instead that success comes with completion, so you can get onto the next thing.
Melinda O. – I guess you could say that my art is simply living by my principles, demonstrating to others that there is a different way to define success, and that they can choose their own measuring stick. I cannot say that I do the greatest job of it some days, but art is about inspiration after all. I aspire to inspire others.
Brendan H. – Three years ago, I would have said this was blog posts. Two years ago, I would have said this was social media. For the last year or so, I would have said this was my podcast. And now, after the birth of my second son, I’m starting to see things a bit differently. The way that I get my message out there is people, not a media. My kids. My readers/listeners/friends/fans. I think that the greatest art IS the emotions and change in makes it others, not necessarily the paint on a canvas. I think that one of the biggest changes that this has caused is that I’m doing more ‘art’ for people and less for the ‘medium.’
Ryan H. – My art is having dynamic, constructive conversations with leaders who have sustained excellence over an extended period of time. I won’t lie… I do check the metrics. I view how many people download and listen to each episode. HOWEVER, it’s far more important and impactful to my life when I get an e-mail from a listener of my show telling me specifically how I’ve impacted their life. Maybe my show helped after they got laid off… Maybe it helped them become a better writer, speaker, creator or art, etc… I absolutely love receiving that feedback and it is the juice that drives me to continually improve as a leader, speaker, podcast host.
Diandra A. – My art is bowling. I learned most of the life’s lessons I know through the sport of bowling. I am now in a position to open up the eyes of others and show them they are doing more than competing in a sport. They are learning some of life’s most valuable lessons. We should all follow fundamentals, but the art in your game makes you unique. I define success based on how much a student’s average goes up. Or, if a young bowler chooses to bowl in college because of my guidance. I define success based on the path that my student’s choose.
Forestine B. – My art is creating specialized greeting cards for people suffering a loss or celebrating a life. I measure success when people spread the word and others come to me and ask me to create a memory card and they trust me to use my own creativity.
Ben N. – My art is often weekly articles to my newsletter subscribers – the Monday Memo – about getting inspired, mastering time management, and building creative habits that stick. Although I can get caught up in my recommends on Medium or email opens, I always try to remember that even one follower is enough. That one person has given me something more valuable than a like or click – they’ve given me their attention and time which is the most valuable resource we have.
Jocelyn M. – I AM an artist, but my art is about showing people that they are valuable and beautiful human beings. Success for me is moving my work forward every day. It can be a small step (getting out the next negative, sketching the next idea), or big ones (preparing my materials, printing the work, writing). But I have to do it every day.
Stephanie G. – My art is making videos, photos, and installations about being black, relationships, and hip hop! I find success in just creating and sharing. I want to do that over and over and over again. For a long time I didn’t make a damn thing and then once I got moving I couldn’t stop and people began to notice and that’s awesome!
Roshni D. – My art is the graphic memoir that I’m currently making. I’ve never written a book in my life, let alone a graphic memoir, but this thing just won’t leave me alone, so I’ve got to write it. How I define success for my art is, how true the portrayal of my feelings is. I am aiming for passion, not perfection. It may be a commercial flop, but I’ll love it anyway, cuz this book is my baby, the expression of my life thus far.
Kelly M. – My art is making buttons (the pinback kind). For me, success is when I see an 80 year old man wearing a button that says “shit works out” (with an image of a poop emoji lifting a barbell), because it made him laugh.
Lou S. – I think I’m still working this out. I love doodling. I can’t stop myself from visualizing ideas. I’m also good at asking the right questions and getting to the heart of things. In the past, I thought writing was going to be my art but now I’m not so sure. I’ve always been focused on wanting to help people, even if its just one person. But just like being focused on numbers/metrics it feels like a lot of pressure every time I sit down. I’ll be honest and say I haven’t really been doodling the last few months. I felt that it wasn’t really helping me or others and that I was just adding to the noise. I still use the skills in my part time job but I don’t do it just for myself. I’m going to reframe this for myself and consider it a success when I get a post / blog out into the world.
Sara G. – I did high school in an art school and in my teens, I thought I would be an artist – I did mostly contemporary jewelry and thought that was my art. It wasn’t. Today I’m a designer. I thought design was limiting, but I realized I don’t need to stay attached to a specific field – design skills can apply to so many aspects of our lives. So, I believe designing is my art as it is the vehicle I use to get my message out there. Success for me is when I create something that helps someone. For example, when I do a branding project and my client loves it – and I feel even more successful when I see the new visual identity I designed is helping that client’s business grow.
Michelle T. – My hair is art. The costumes I put on my dog is art. The way I “bling” my phone is art. The stickers and fuzzy steering wheel on my car are also art. And my music as a percussionist is my art. My LIFE is art! It took me many years to stop worrying about what people thought and just to try things. Now I’ve tried so many things that I would have never had the guts to try! I define success when I can touch the lives of others. When someone says that I helped them in some way by something I have written or have brought them joy while they were listening to (or watching) me play. There is no better success to me than moving someone by doing something that I simply love to do anyway.
Brad M. – My art is split into two things: The first is my writing, my blog posts that I write every week. The second is my interactions with people either through my speech coaching or through my study abroad peer advisor job. I actually really enjoy the second type, because unlike my writing it is much harder to get hung up on getting it perfect. Each interaction is by nature limited in the amount of time you can spend on it and once it is done there is no chance to get back and edit it. It encourages you to let go and focus on the next interaction. For my writing I label an article a success by whether a single person found it useful (even if that person is me!). It’s a humble metric but I like it that way. For my interactions, that is much tougher. So far I think I label it a success if the person walks away from our session happier and more confident (either in their public speaking ability or in their ability to go study abroad). I think that is the real goal of my interactions. I want to make people smile and more aware and confident in their own abilities.
Jason K. – I am an “artist” artist. I draw and paint. But I also I create things — not just art objects — but observations, and connections and experiences that give people hope and the freedom to live joyfully. 2) This year, I have started a “Tinker Project” which was born out of my desire to spend more time in the studio. The last few years, during my annual review process, I alway felt disappointed that I didn’t spent more time making art. (Other business pursuits always seems to take priority.) This year, I said enough is enough, and committed to making 100 new pieces of art, which has required my to set aside one day a week as a Studio Day. So far, so good. I haven’t missed a Studio Day, and through March, I’ve made 28 new pieces. Not only does that put me ahead of the pace I need, it’s only one short from the total number of pieces I created last year. Although I suspect good things will come from this project and the art I create, those things are not my primary indicator of success. If I end 2016 with 100 new pieces of art, I will have succeeded in knowing that I finally made my art the priority it needs to be.
Eyram S. – For me, my art is combining Engineering, Art and Memory into a new way for engineers to express their talents, frustrations and creativity – without having to stress out about companies and exams. I think we are really hitting a point where this needs to hit home – we are human beings, not robots. I’m realizing that shipping and tracking how I feel (and my reader feels) about the article as the main metric. My metric is engagement. If I get a lot of replies to my email, I’m doing something right. If I hit my 1,000 True Fans (as everyone always recommends but never does as a metric), I’ll be the happiest 1st gen African-NYCer alive.
Eric R. – Over the last couple of years though, I’ve found that how we approach life can be art. How we are in our relationships. How we show up in the world. Being a parent (sculpting the life of another human). I am realizing that for me, the measurement of success is showing up. Pushing through doubts and fears and doing it anyway. Recognizing that you can look at things from many perspectives and if you stay true to your values and who you are, the metrics don’t matter.
Pedro C. – I’m a painter. I love art and I draw and or paint because I have to. If a piece becomes a favorite it’s not up to me. It’s up to the audience. I’m very interested in marketing and providing value to my audience. I sometimes think art is my Trojan horse.