I want to be my own boss

I Want to be My Own Boss: How to Make it Happen

Julie Ewald Entrepreneurship, Inspiration, Job Search Leave a Comment

I’ve met so many people who echo the same sentiments:

I want to be my own boss.

And even among those who haven’t come right out and said it, entrepreneurial thinking and a desire for some degree of self employment is on the upswing.

A few years ago, MarketWatch reported that half of employees in their 20s and 30s really would prefer to be their own boss. And according to Inc, 63% of adults under 30 want to run their own business–if they don’t already. Then there’s the report shared by HuffPo announcing that a whopping 72% of high school students want to be entrepreneurs.

With stats like that, it shouldn’t be surprising that people are starting new businesses in droves, right? Well, it wouldn’t be surprising… if it were true.

The reality is that while most people say that they want to be their own boss, they don’t make it happen. 

There are a lot of reasons for why “I want to be my own boss” never translates into actual self employment. An interesting post on Entrepreneur introduces you to eight types of people who won’t successfully start a business. And while the generalizations there are pretty sweeping, I think these archetypes of non-entrepreneurs will sound all-too familiar to some. Have you ever experienced failure to launch?

From getting wrapped up in the planning to irrational fears to a straight-up lack of skill, there’s a range of reasons why entrepreneurship is illusive.

I think that a big blocker to self employment is not pursuing the best avenue to entrepreneurship for you. Just as not everyone is destined for success as a digial nomad, not everyone should expect success with any entrepreneurial endeavor they try. It just may not be a good fit.

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So what makes a good fit?

It’s hard to say.

I believe it’s a combination of factors that come together to make a perfect storm for success for one business idea. And these same factors could make another one absolutely destined to fail.

In terms of which of these factors are the most impactful, I think it varies. It’s dependent on who you are and what path you are trying to pursue. But in the most general sense, I think the following are the big ones to watch if you want to turn “I want to be my own boss” into “I am my own boss.”


You don’t need to be rich to start your own business, but if you don’t have enough money to start and run your business… yikes! You could be setting yourself up for failure.

The amount you’ll need will vary from endeavor to endeavor. If you are going to start doing freelance writing, you may not need a cent, but if you are buying a food truck, tens of thousands should be in the bank. If you don’t have enough of a budget, there is a good chance you’ll go broke before you get started. Or shortly after you “open” up shop.


Are you passionate about what you want to do? You don’t need an all-consuming fire or a compulsive obsession. But you do need to have some degree of the feels for what you want to do. If you aren’t keen on your chosen path to self employment, the odds are good you’ll lack motivation and followthrough. You won’t be your own boss for long if you don’t have any drive to do any work.


You need the ability to do the job you create for yourself. Full stop.

I think the most obvious example of this is in the restaurant and bar industry. Lots of folks try to open a bar or eatery, but they have no experience even working in one. And many of these folks give themselves the job of general manager, head chef, or lead bartender. Then they’re in shock when the business fails!

A much more subtle, yet equally pervasive, example is in the freelance world. Many folks are trying to make a go as a freelance writer, web designer, or graphic artist… that don’t know how to be a writer, designer, or artist. They can’t get a single gig on Upwork--at least not one that’s high paying because they don’t know enough about their chosen line of work. Some of these folks then learn the skills, but others fizzle out.


If you can’t self manage, you probably can’t be successfully self employed. There are a lot of distractions in the world, and some folks will chase all of them, if they could. There are some people that need some level of accountability (like a boss!) to keep them on task.

Don’t fret if you lack focus now. It can be learned. Seriously. Check out these tips on LifeHack; I think they’re a good start.

Also, I think passion and skills play into focus. You’ll be more into what you’re doing if you like it. And if you know what you’re doing and aren’t struggling, you are also likely to experience greater focus.

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I want to be my own boss… now.

Okay, I get it. Enough of me. You’ll never get started as an entrepreneur if you just read blog posts all day!

And while you’re getting your ducks in a row, remember this blog post! Please come back and share any relevant articles, tips, tricks, and advice you find in the comments. Your fellow entrepreneurially-minded folks will thank you!


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