6 Signs Self-Employment Isn’t Right for You

August 28, 2015

Connect Member

Personal finance expert at Creative Money: a resource for gaining clarity & confidence about money.


When I made the decision to become self-employed 15 years ago, it was because I saw working for myself as the single best way to never limit my income potential. While I am very satisfied with the “Three Fs” of self employment — finances, flexibility, and freedom — I have made decisions about my life and challenged myself in ways that would make a lot of people uncomfortable. I have started and sold two businesses, completely screwed another up, and took far too long in my current one to get online. It’s been quite a ride.

Self-employment isn’t for everyone. Here are some of the common ways that people derail themselves in self-employment.

1. You Can’t Settle on an Idea
I love the idea of an entrepreneur with many passions, and I admit that I get bored if I have to do too much of the same thing all of the time. However, if you flit around from business concept to business concept, you never gain a firm footing in any of them. Start one idea, and then, when it’s profitable and self-sustaining, move on to the next.

2. You’re Not Willing to Vet the Idea
I meet people all the time who are convinced they have a profitable business idea, and then want thousands of dollars to invest in the business. Do some research first. Start small. Consider getting hired as an employee at a competitor for four to six months for an inside look at operations. Perform a small test case to prove your theory before investing in a new idea.

3. You Have Trouble Self-Starting
I used to be one of those employees that needed zero management. I just got stuff — a lot of stuff — done. I’m the same way in my business. Believe me, I have plenty of flaws, but being a self-starter and doing what I say I am going to do in record time has saved me in self-employment. If you’re already self-employed and have issues with this, the best thing you can do is hire yourself a weekly project manager to keep you working close to your revenue line.

4. You Have Issues With Self-Worth
Some people feel like they don’t deserve to be paid for what they do, but this could be a whole post in itself. I’ve spent the past 15 years building confidence in this area, but it’s been a bumpy road and an ongoing process — something that I constantly have to challenge myself with to continue to grow. Yes, even after 15 years.

5. You Tend to Freak Out When Things Go Wrong
If I panicked for days every time someone questioned my worth, someone unsubscribed from my email newsletter, my income went down a little, or something didn’t go my way, I’d be a basket case. Emotional competence isn’t about never getting upset; it’s about how fast you can get back on track when you’re thrown for a loop.

6. Your Mate Isn’t on Board
I’m not married, but I meet entrepreneurs all the time who are terrified that they will lose the trust of their spouse or have to go back to employment if they don’t succeed. The solution isn’t to leave your spouse; it’s to know that this is a minefield that you have to negotiate. Make sure you have agreement over the vision as well as a plan in place for the other potential obstacles to business success. Talk with your mate. Often, self-employed people forget to include their mate in their business plan, but like it or not, they own 50 percent of your business. They deserve a voice.

Above all, to get a business up and running, you need to prioritize your life. What other areas of your life are you willing to fail at in the short term to achieve stable self-employment? When I first became self-employed, I didn’t do anything for the first 24 months but work. I didn’t have a choice; I had to support myself. Are you willing to sacrifice for the big picture?

Mindy Crary is a member of the DailyWorth Connect program. Read more about the program here.