Once an Entrepreneur, Always an Entrepreneur?

I talk a lot about making the leap to entrepreneurship. Most of my clients are people who are doing exactly this, and as an entrepreneur myself, I live and work the lifestyle. Three years after launching my business, I can’t imagine life any other way. I love helping my clients discover work that lights them up, and I love working and living on my own terms.

But can the entrepreneurial leap be done in reverse? Do people who build small businesses who have transitioned to working for themselves make the switch back into the traditional workforce or pursue opportunities outside their business? Increasingly, it seems so.

When it comes to entrepreneurship, there’s no one-size-fits-all business model, and that’s one reason why people are so drawn to it.

With that in mind, it makes sense that people tailor their businesses to meet their evolving personal and professional wants and needs. There are all types of variations: entrepreneurs with small businesses who consult on the side and end up stepping away from their business to work for a consulting client full time; entrepreneurs who take on side work that’s separate from their business (often in industries like copywriting, graphic design, and fitness class instruction); entrepreneurs or consultants who work part-time jobs in addition to running their small business; and finally, people who step away from their small business for a full-time job, effectively making the entrepreneurial leap in reverse.

In her Forbes.com article, “This Is How You Know You're Not Meant To Be An Entrepreneur,” fashion industry veteran Aliza Licht sheds light on her own experience with entrepreneurship. After leaving her 17-year career at DKNY, she started her own consulting business. “Being on my own was exciting,” she writes. “The possibilities seemed endless.” But after 10 months, she took stock of her progress, and felt very differently. “The truth was, I wasn’t impressed. Sure, if I looked at my calendar, it looked good. Meetings were happening and connections were being made, but it wasn't moving the needle. I didn’t want ‘it’ enough; that hustle, that passion that makes people strive as entrepreneurs was totally nonexistent from my headspace.”

I think about this article often. Licht’s insights are spot-on: she acknowledges how empowering it is to be your own boss and have freedom in your schedule, while also recognizing that being an entrepreneur is not for everyone. It can be lonely, and many people miss being part of a team and working collaboratively. Realizations like these eventually led Licht to rejoin the traditional workforce, leaving entrepreneurship behind without regret.

Many people who go back to a traditional role want stability in some form. It’s no secret that it’s financially scary to be self-employed: you don’t always know how much money is coming in, you have to take care of your own health insurance, and you miss out on the benefits that often come with salaried jobs. This stress is multiplied if you happen to be starting a family; if you’re an independent professional, you likely don’t have the safety net of maternity or paternity leave or benefits. The scarcity or lack of benefits alone, whether maternity, paternity retirement, or fringe, is enough to drive people back into a traditional roles.

But there are also the reasons that Licht touches on, which have more to do with personality, working style, and your overall goals for your career. As rewarding and energizing as it can be for some people to build and grow a business, it can be depleting for other people. It also has to do with opportunity. Sometimes, a job offer crosses your path that you can’t pass up. When you aren’t expecting something to fall into your lap is often exactly when it happens.

If you’re someone who is considering leaving your small business or stepping away from entrepreneurship, my advice is to make a pros and cons list in as much detail as you possibly can. Really dig deep and work to determine exactly why you want to make this transition. The prep work you did when you started your business can be very helpful here. What motivated you to become an entrepreneur? Have those factors changed considerably? If so, how and why? There is absolutely no shame associated with any reason (whether it’s more money, more stability, or whatever it may be), but the purpose of the exercise is to determine whether your gut is truly telling you to leave, or whether you’re experiencing a temporary slump in morale or enthusiasm.

I always advocate for talking to people who have gone through similar experiences with their businesses and can listen or give advice. While no two situations are exactly the same, other entrepreneurs have likely gone through something similar, and they may be able to relate or provide tips if you’re interested in hearing them. You may still decide that it’s time to make a change, and after you’ve investigated why you feel that way, do what’s best for you, your career, and your lifestyle. As Licht writes of her decision to take a new full-time role, “My power lies in being honest enough with myself to know when the path has ended and I need to make a turn. It’s about understanding my strengths and my weaknesses and learning how to apply the strengths to enhance my growth. I am thankful today for clarity.”

When I say that I would never stop being an entrepreneur to go back to working for someone else, I inevitably come across people who say, “never say never.” And that’s valid, but for now, I really believe that being an entrepreneur serves me best, both personally and professionally. It’s not something I did on a whim or took lightly; I’ve known I wanted to be an entrepreneur since I was a teenager. That belief was confirmed every time I worked at an amazing company or for an incredible boss and loved the experience, but still looked forward to the day when I would work for myself. If I did return to a traditional role, I know that my experience as an entrepreneur would heavily inform the type of industry and the working environment I would choose. To compete with my business, the opportunity would have to be laser-focused on something I truly love.

Even if I was not officially working in an entrepreneurial capacity, I would still maintain my entrepreneurial spirit. After all, it’s what drove me to start my business in the first place. The experience I’ve accumulated and skills I’ve developed as an entrepreneur will, going forward, always be part of who I am and how I work. I think the same goes for anyone who has built something from the ground up.