What to Do When You Realize Entrepreneurship Isn’t Your Dream Job

Photo by Nik Shuliahin on Unsplash

It happens more often than we usually realize. A young professional dreams of owning their own business, then steps into the role with energy and enthusiasm. They spend a few months, or even a few years pursuing their dreams — and regardless of whether they’re successful or not, they come to a harsh realization. Entrepreneurship isn’t the dream job they thought it was going to be.

If this is you, what do you do next?

Step 1. Analyze

First, take a moment to analyze the situation. Entrepreneurs tend to think and move fast, so there’s a chance you may have gotten ahead of yourself. Are you truly dissatisfied with entrepreneurship in general, or are you experiencing a temporary period of stress? Is this a result of pure experience, or did you build up your expectations for the position too much before you got started?

More importantly, try to analyze the root causes of your feelings. Entrepreneurship involves many responsibilities and moving parts, so it’s hard to write it off completely. Is there one responsibility, or one feature of entrepreneurship that’s making you especially unhappy? Can you imagine yourself happy as an entrepreneur of a different company? How about as an employee of another company?

Once you have the answers, or at least a direction, you can start considering your options.

Step 2. Transform

You’re in charge here. You have the power to transform this company, and your position, however you want to. The idea of a major change may be uncomfortable to you or your staff at first, but it’s worth the risk if it means creating a better environment for yourself (so long as the function and profitability of the company remain in good standing).

For example, you may change the company culture slightly to create a workplace that makes you more comfortable, such as one that’s more laid-back, or one that’s more rigid and schedule-focused (depending on your preferences). If there are specific responsibilities you hate, such as sales calls or managing human resources, you can hire someone to take over those tasks.

Step 3. Cope

After you’ve transformed as much as you can, or if you can’t transform anything, you may still feel dissatisfied with your position as an entrepreneur. If that’s the case, you can experiment with new strategies to cope with the stress and discontentment you’re feeling. It’s important to take care of yourself, physically and mentally, while you’re in such a demanding position.

Start by taking a vacation, as soon as possible. Get away from the office for a week, and don’t cheat by checking your emails while you’re gone. Take more regular breaks, and more personal time to spend with your friends and family. Eat healthy, exercise, and even try regular therapy sessions if you’re really struggling. You may find, especially after a few weeks of better self-care, that your feelings were symptomatic of an unhealthy work-life balance, rather than displeasure with entrepreneurship in general.

Step 4. Adopt a new role

If you still find your position as a CEO or team leader undesirable, but you still want to keep your ownership and involvement in the company, consider taking on a new role, such as one of these:

· Partner. You could bring someone else on to help you co-manage the responsibilities you currently bear. You’d likely have to split ownership of the company at this point, but it may be worth it if you need more hands on deck.

· Consultant. You could also serve as a consultant, possibly writing for the company blog and providing advice to whoever replaces you, but from a distance and on a schedule you prefer.

· Worker. If there’s a niche area you prefer to work in, such as programming or marketing, consider transitioning to become a worker within your own company. You’ll still carry tremendous respect, but with less pressure and fewer responsibilities.

Step 5. Start Fresh

If none of that works, consider whether entrepreneurship could work for you in a different application. Serial entrepreneurs do tend to be more successful, but that doesn’t necessarily mean you’ll be happier. After learning from the mistakes that led to your dissatisfaction in your first company, you may be inclined to forge a different position for yourself in the second, or choose a different industry that’s more to your liking.

If entrepreneurship really isn’t for you…

If entrepreneurship just isn’t right for you, the only thing left to do is find a different career path entirely. That may seem intimidating at first, but there are limitless options waiting for you. You could go back to school, find a mentor, or revert to an old field you found fulfilling in the past.

The good news is, your experience as an entrepreneur will help you no matter what you do next. You’ll be more decisive, more confident, and you’ll have more perspective to bring to the table.

For more content like this, be sure to check out my podcast, The Entrepreneur Cast!




CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!

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Jayson DeMers

Jayson DeMers

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!

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