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Stay in Business for Yourself or Work for Someone Else: Is It Time to Hang Up Your Solopreneur Shoes?

Stay in Business for Yourself or Work for Someone Else: Is It Time to Hang Up Your Solopreneur Shoes?

A couple of months ago, my business started to slow a bit. I’ve worked for myself long enough to know that there are natural ebbs and flows, with some times of the year being more lucrative than others. However, the unknowns created by the pandemic caused me a bit more concern. How long would this downturn last? Was it time to get more work?

After a few weeks of being less busy than I’d like, I made looking at job boards a daily task. I knew if I could just add one more consistent client to my roster, I’d be all set. So, that’s what I set out to do. Within the next 30 days, I secured a part-time gig, which was just enough to fill my newly open time. Crisis averted.

Fast forward to about a week ago and I received an email from one of the other companies to which I’d applied. They were interested in learning more about me and wanted to move forward with the interview process. Since I like to keep my options open, we set up a call.

Upon speaking with them on the phone, I learned that this position was full-time. Technically, I could still keep my current business on the side, but I wouldn’t have to, as the money was enough. I have to admit that the appeal was there. If I secured this new position, it would mean regular pay, medical benefits, and no more days off without wondering what it would do to my income. I knew that I had a decision to make.

I could either stay in business for myself and accept all of the uncertainties that come with being a solopreneur or I could hang up my self-employment shoes and return to the world of employment. If you are in the same boat, wondering which decision is right for you, here are a few factors that I found helpful to consider.

Flexibility vs Stability

Being a solopreneur means that I have maximum flexibility with my days. As long as I get my work completed, it is largely up to me what times of the day I work. This works well on nights when I can’t sleep and find myself awake at 2:30 am. I’m able to go to my home office, type up a few pieces, and use that time to my advantage.

Working for someone else means that I give up this flexibility, at least in part, because I need to be available during typical workday hours. Yet, the trade-off is stability. I know that a certain sum of money will be deposited in my checking account regularly. No more ebbs and flows. I would also have medical and dental insurance, access to a 401k, and even stock options.

Is one factor more important than the other? The answer to that question varies from one person to the next. Some people favor flexibility whereas others like the reduced stress of stability. To me, what is critical is being honest about what each one means in your world. Maximum flexibility is great, but not if it causes you so much stress that you have health issues. Stability is great too, yet not so much if you feel stifled and begin to dread your workday.

It may help to take a few minutes, close your eyes, and really think about what your day would look like under both circumstances. Mentally go through the motions and pay attention to how you feel. Which one brings about the most positive emotions, and why? Does one reduce your tension more than the other? What does your gut tell you about which option may be better for you?

The Money Factor

Some people make their decision to leave solopreneurship based solely on money. They’re tired of the financial hills and valleys of business ownership and like the idea of a steady check. In some cases, this check may be more than you earn now. This can make the decision even harder.

To complicate the issue even more, you have to consider not only the money that you make today, but also what you can potentially make tomorrow. Even if you aren’t at the income level you want right this moment, you can get closer by getting more clients, increasing your rates, or a combination of the two. Of course, this isn’t always an easy process, but it still needs to be considered when making the decision.

If you’re presented with a good financial opportunity by working for someone else, it’s helpful to think about what the money represents. Does it mean that you’re one step closer to retirement or does it mean that you can actually afford to eat this month? Answering questions such as this can help make your answer clearer.

No, money doesn’t buy happiness. But it can increase your peace of mind. So, if you find that financial stress is taking its toll on you mentally (or even physically), it may be more appealing to work for someone else.

If this is what you decide, this isn’t necessarily a step back. It’s more of a step toward greater mental health, which is nothing bad at all. In fact, that may be a good thing!

Nothing Is Permanent

It’s also helpful to remember that, in life, nothing is permanent. Whether you decide to remain a solopreneur or work for someone else, if you find that it doesn’t work out as you had planned, you can always choose to make a different decision tomorrow. You’re only stuck if you allow yourself to be.

Developing an all-or-nothing perspective can make the decision more difficult because you feel like choosing a certain path forces you to follow that path to the end. But that’s not the case. You can always change your path mid-journey or turn around and come back to solopreneurship if you find that the employee path doesn’t feel right to you.

In some cases, you may be able to do both: work for someone else and do your own thing on the side. You may find that this provides both flexibility and stability. It does mean more work, but if you don’t mind that, it could offer the best of both worlds.

After considering all of these factors, I have decided that I’ve worked too hard the last decade to build my business to walk away from it now. So, I’ve withdrawn my application and left that opportunity for someone else.

The best part is that I’m proceeding with solopreneurship with a renewed energy, because I’ve taken the time to really think about what being a one-person business means to me. In that regard, this has been a good process because it has helped me remember why I am willing to go through the ebbs and flows. In the end, they give me the life that I want. I hope that you find the life that you want too.


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by Christina DeBusk // Freelance writer, author, and small business consultant committed to helping entrepreneurs achieve higher levels of success.

Opinions expressed by contributors are their own.