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10 Entrepreneurial Lessons From 10 Years of Experience

Wandering Aimfully Through Running A Business

10 Entrepreneurial Lessons From 10 Years of Experience

After 10 years of working for myself here are 10 lessons I've learned and want to share with you.
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

On September 24, 2008 an idea hit me that completely changed my trajectory in life and business. I was going to ask the world to pay me (a nobody living in Florida at the time) to wear a sponsored t-shirt and create content on social media. At the time there were barely any people on Twitter, Facebook was still a closed platform (you had to have a college email address), and being a “vlogger” wasn’t a thing on YouTube. But it wasn’t just my IWearYourShirt idea that kicked off on that day, it was the decision to work for myself and run my own business.

Since that day day in September of 2008, I’ve learned an immense number of valuable lessons. I’ve written two books (#1 and #2) that go into greater detail of my entire entrepreneurial adventures, but I thought it would be fun to give you an abridged version with 10 entrepreneurial lessons that may help you if you’re currently working for yourself or thinking about working for yourself.


Lesson #1: It takes work and effort (there are no shortcuts to success)

Many times during these past 10 years I’ve tried to skip the hard work I knew it would take to launch a project, build a website, manage customers, etc. I wanted to believe the shortcuts, cheatsheets, and blueprints that other people were offering could help me skip the hard work and patience it actually requires to succeed when working for yourself. I was wrong. Every time. If you aren’t willing to do the work, in whatever shape or form “the work” takes, you will not succeed. But if you are willing to put in the hours, the effort, and push through tough/ambiguous times, you will be successful (however you define that success).

Additional reading: What It Takes To Be An Entrepreneur


Lesson #2: I wish I would’ve defined what my “enough” was earlier on

It’s unbelievably easy to let our brains get caught up in the trappings of more. To crave more money, more attention, more likes, more everything. It would’ve saved me a lot of mental battles and money had I been willing to sit down and clearly define what “enough” meant to me. These days Caroline and I always define what our enough is for anything that can be measured (the amount of money we can make, the amount of subscribers we can get, etc). By drawing a clear, realistic, line in the sand of where we’ll be happy, we’re able to enjoy every part of the process and never get stuck dreaming for bigger and better.

Additional reading: Why You Should Focus on Enough Instead of More


Lesson #3: Test all of the assumptions all of the time

Have you ever had these thoughts: “I don’t know why someone would buy from me” or “too many other people are already doing XYZ thing I want to do.” Those and many other assumptions will stop you dead in your tracks before you even have a chance to see if they’re correct or not. I feel very fortunate that I’m wired to question every thing in life, at every turn. Now, my family and wife may have some thoughts about how that way of thinking can be a bit of a pain in the ass, but it has served me well in business to never get stuck worrying or letting self-doubt stop me before I got going.

Any assumption you have, especially about business, should be tested with actual data and proven right or wrong. Also, if you’re sharing your ideas with friends and family, they will absolutely share their assumptions with you. Don’t let THEIR fears stop YOU.

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


Lesson #4: It’s helpful to learn the basics of code, SEO, marketing, sales, and accounting

I’m a big advocate of outsourcing your weaknesses and not spending time doing things you aren’t good at or don’t want to do. However, learning the basics of HTML/CSS, SEO, marketing, sales, and accounting, can help you speak the language of the people you are outsourcing to. There are multiple times in the past decade when I blindly accepted someone’s advice thinking I could trust them on their word, only to find they did crappy work that had to be redone. Had I known the basics of what they were working on, I could have asked the right questions along the way and avoided the headaches.

You don’t need to become an expert in anything you aren’t going to use on a daily basis, but you should arm yourself with a basic knowledge so you’re not completely in the dark and having to rely on trusting strangers with your business.

Additional reading: Outsource Your Weaknesses To Run A Happier and Healthier Business


Lesson #5: Don’t do it alone

The first couple years of my entrepreneurial journey I would’ve benefited from having a mentor or a coach. Someone with experience who could’ve guided me through situations that most business owners encounter. Instead, I was too proud to ask for help (the next lesson will address this). I believed I could do everything myself and that I didn’t need any help. Wrong. When you’re working for yourself, having someone you can confide in, brainstorm with, give you time-worn advice, and set you straight when you’re veering off your path is immensely valuable. Having Caroline come into my life hasn’t just been amazing for me personally, but she’s someone I can talk to at a moment’s notice who’s smart, creative, experienced, and extremely supportive. I 100% realize you may not have a Caroline in your life (sorry!) but you should absolutely try to find a person or a community that can support you on your journey.

Additional reading: Bad Friends Are Toxic, Here’s Why You Should Reevaluate Friendships


Lesson #6: Pride can be helpful to push through tough times, but it can also keep you trapped

Pride is probably one of the biggest double-edged swords for me in the past 10 years. While it’s been part of my success to put my crazy ideas out into the world, it’s also been my downfall on many occasions. My pride got me into $100,000+ in business debt. My pride burned a bunch of relationships over the years. My pride kept a project going longer than it should have. My pride has kept me trapped a few more times than I’d like to admit, and I don’t wish that for you. The best advice I can give when it comes to dealing with your pride is in Lesson #2: define your enough. By establishing clear boundaries of enough, you can keep your pride at bay.

Additional reading: It’s Okay If You’re Feeling Lost


Lesson #7: Empathy goes a long way (in sales, in customer service, in being a relatable human)

There are lots of little moments throughout the past 10 years where I’ve put money aside and opted for being a good human over being a ruthless business owner. Whether it was as simple as giving someone a refund or spending thousands of hours replying to emails from people asking for advice, empathy can go a long way. You can’t see empathy on a Profit & Loss statement, but being an entrepreneur isn’t just about profits for me. It’s about being helpful and about passing on all the lessons I’ve learned in every aspect I can. It’s about treating people with respect and trying to give more than you get. The long-term side effect of operating with empathy is attracting a group of customers who are loyal and who feel appreciated by you.


Lesson #8: Putting up a website without promoting it is like building a hotel in the desert

Every idea I’ve had since 2008 has had a website. I’ve spent so much time, energy, money, and effort to make my websites welcoming, fun, and informative. But all that effort would’ve been worthless if I didn’t spend the time to promote my website and use my creativity to help people find it. Much like building the most beautiful hotel in the middle of the desert, if you don’t tell people it exists and build roads to it, no one will ever find it. I believe there is a clear path to running your own online business and helping people find whatever you’re building:

  1. Create consistent and authentic (to you!) content (articles, videos, etc.)
  2. Build an email list that shares your content on a recurring basis
  3. Come up with ways to get your website in front of people so they can find your content
  4. Deliver value as often as possible to your email list (that doesn’t mean discount codes)
  5. Focus on being helpful or entertaining in everything you do

Exciting and shiny social media channels will come and go throughout your time building your own business. Being helpful and actually showing up for your customers never goes out of style. There’s no algorithm that can stop you if you’re willing to do consistent creative work.

Additional reading: The Ethical Guide To Building An Email List Without Sleazy Tactics


Lesson #9: It’s a 5-10 year process to get true clarity and stability in your business. Be okay with this.

I bought in early on entrepreneurship. The day I stood in my closet 10 years ago and committed to starting IWearYourShirt was the day I also said, “I’d rather work for myself for the next 30-40 years than show up at a job that takes 1/3 of my life from me.” So many aspiring business owners are dreaming of a magical payday that will never come. If you simply accept the fact that working for yourself is a gift and something you can enjoy, you’ll be okay with building your next thing for 5-10 years and planning to continue to do it well after that.

I’m at year 10, and yet I feel like we just hit the reset button on the video game of our entrepreneurial lives. We have a brand new business, website, podcast, content strategy, customer base, etc, and while it can seem daunting, I also understand that I have 10 years of experience and lessons learned I get to apply to this recent reset. It’s not going to be easy, but I know we’ll avoid the missteps and traps I’ve fallen into in the past.

Find a way to enjoy the process and your impatient desire to have it all fall into place overnight will start to disappear.


Lesson #10: Is where you are today where you dreamt you’d be a few years ago?

In other words, be intentional about appreciating how far you’ve come. This is probably one of the most helpful thoughts you can have when working for yourself (or just being grateful for where you are in life). Is where you are at this very moment a place you could only dream of a few years ago? It’s easy to get stuck and think things aren’t perfect in your life/business, but if you look back to where you were a few years ago and realize where you are today is some semblance of a dream come true (no matter how small the dream is), take that moment to be grateful. If you aren’t where you wanted to be, what are YOU going to do to make your dream come true in the next few years?


I’m so incredibly grateful that 10 years ago I took a risk on myself and a crazy idea I couldn’t let go of.

It led me down a path that brought me to this moment and this life, and that’s pretty darn cool. Whether you’re at the beginning of your entrepreneurial journey, or like me you’ve been at it for a decade… here’s to the next 10 years!

10 Entrepreneurial Lessons From 10 Years of Experience

(Big Fat Takeaway)

It's never too late to make changes in your life or business. Accept that working for yourself is an ever-evolving thing and success will come much easier if you can enjoy the process as much as possible.


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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