If You’re an Entrepreneur At Heart, You Need to Take the Leap and Work for Yourself

By Dan Dowling

The idea of working for other people always seemed stupid to me. So when I worked the normal jobs I was expected to, I was never really there: I couldn’t get into something that I hated, let alone excel. I didn’t know that working for myself was an option yet.

So I always burned out and quit my jobs or got fired.

It sucked that I didn’t have money, but worse was the toll it took on my confidence. Each time my square-peg self tried to fit into a round hole, I identified more and more as a failure. That’s not exactly the attitude you need if you were born to be a solo entrepreneur like I was–and maybe like you are, too.

After about four failures-to-launch — leaving home again, coming back; leaving home again, crawling back — I was a 24-year-old locked in existential crisis, succumbing to panic attacks up to 10 times per day, wondering what I was on this planet for if all I could do was fail. And my options were clear:

1) Learn how to work for myself–follow my own path. Or 2) go insane and die of a stress-induced heart attack before age 30.

That’s when becoming a solo entrepreneur became my only path.

From that rock bottom I had to build my confidence, tear down my old limiting dialogue (which was a herculean effort in itself) and relearn how to be me. That process took two years, and luckily I had my parents to support me, or I would have been homeless. But all the while I was orienting myself day by day to become disciplined and consistent enough to thrive as a solo entrepreneur.

Two years into my self-improvement journey, after eliminating my low-value habits and sticking with awesome things like planning and journaling, I was fully supporting myself by writing what I wanted to write, on my own time, for myself, and making my work appealing to big markets. It was a dream to finally be a functioning member of society. But more than that, I was doing it on my own terms.–That’s what made the experience so magical, and the impossible-seeming efforts of being a solopreneur worth it.

Expanding my solopreneur journey

After reaching success on many of the world’s largest publications, I started making even more money by coaching fans of my work on how to rapidly and massively change their lives, and how to break into their own work, too.

The funny thing is that when I started out, all my clients made 5-10 times more money than I did. But they didn’t care. They actually conceded that I was much farther along because I was doing what I wanted, when I wanted, helping the people I felt called to help, and making money working for myself. I had purpose and passion where they didn’t. And I had tons of free time to do all the stuff I loved.

That’s life as a solopreneur. And that could be your life.

When will you follow your calling and work for yourself?

How much more can you take? How much longer will you follow orders of people who don’t care about you or your family or your ambitions? How much longer will you think that working for others is the dumbest idea in the history of the universe, only to put in half-assed efforts, earn half-assed results and feel less than half-ass of a human being?

How much longer will you delay the start of your solopreneur journey?

If you like working for other people, I’m not talking to you. If you’re even okay with working for other people, I’m still not talking to you.

I’m talking to the natural born entrepreneurs who when given the choice would rather cut their own hands off with a dull spoon à la Aron Ralston (you know, the guy who the film 127 Hours was based on–and it wasn’t actually a spoon; it was a very dull knife) than be forced to work for anyone but their own selves. I’m talking to the talented and inspired individuals who either “succeeded” but felt empty because we didn’t succeed at being ourselves, or we were ignominious, non-functional disasters like I was.

You can choose to be yourself and be happy, taking the obvious risks of failure, but having faith in your ability to succeed–which takes a lifelong commitment to self improvement. Or you can choose to be a walking existential crisis and to continue obeying orders from people who don’t give a s#!% about you, and die knowing that you never actually lived.

If you’ve made the decision to work for yourself, or if you’ve already made that decision but haven’t gotten the results, here’s how to make it happen today:

1-Define how you will immediately start making money on your own–brainstorm your skills and passions, then figure out the realistic first steps. Compile those steps into a monthly goals sheet.

2-Identify the material you must study in order to make your craft valuable enough to sell. Create daily study goals.

3-Commit to a certain amount of daily work towards your solopreneur goals. It’s far better to do just thirty minutes every day than to do a couple hours once a week. It’s all about the daily effort!

4-Identify the timewasters that are holding you back and the habits that drain your confidence, and add those “not-to-do’s” to your monthly goals sheet. Time and confidence are the most important commodities for solopreneurs.

5-Create a weekly action plan from your monthly goals every Sunday. Identify the things you must do every day to be successful in whatever it is you decide to day: mark them as non-negotiable goals. And then create daily planning pages every morning to keep yourself accountable to the goals that will make your solopreneur dreams come true.

If you have any questions or comments, shoot me an email. But if you’re serious about investing in your success and wellbeing, check out my solopreneur coaching program.


Written by Daniel Dowling
I went from being a highschool and college dropout to writing for the world's best publications in two short years. I owe ALL my success to habits like mindfulness and journaling. - So I built Millennial Success to share those incredible habits with you!