10 Regrets Most Entrepreneurs Eventually Face

January 22, 2016, 2:46 PM UTC
Young businessman on phone with head in hands
Photograph by Leonora Saunders via Getty Images

This piece was originally published on Entrepreneur.

From the time you first start thinking about owning your own business to the day you open the doors, entrepreneurship seems like an exciting, challenging, gratifying experience. Even the stressful moments have a bit of magic to them; you go to work, knowing that your mistakes will likely be little more than temporary setbacks that teach you lessons about how to conduct your business.

With all that in mind, it seems crazy to think that someday you may look back with regrets about some aspects of your earlier approach. But in fact most entrepreneurs eventually find themselves in this position.

Typically, these regrets aren’t as big as, “I wish I hadn’t started a business,” or as petty as, “I wish I hadn’t hired so-and-so.”

Rather, they focus on missed opportunities, untapped potential and other unknowns that you’ll never get to discover:

1. Moving too fast

No matter what your goals are — making a ton of money, getting to a stable place, leaving a reputation behind or becoming known — it’s tempting to scale as quickly as possible. You’ll want to hire more people, expand to new locations and invest more money in your marketing. But be careful: Moving too quickly can cause instability, and may expose vulnerabilities that weren’t present in your original state.

2. Playing it too safe

On the other hand, moving too slowly can end up causing just as much regret. Entrepreneurship is a game of risks: To stand out from the crowd, you have to be new, bold and unique; and you can’t acquire those qualities unless you go out on a limb. So, venture on out there. If you stay too safe, you’re bound to miss out on some major opportunities.

3. Burning bridges

Few people intentionally burn bridges out of spite, but as entrepreneurs, we often let relationships decay or slip away without hope for recovery, if for no other reason than the sheer number of relationships we have to keep up with.

Sooner or later, you’ll lose a client or an employee and think nothing of it — only to realize what you’ve lost some time later. Preserve as many relationships as you can.

4. Focusing on a product instead of a consumer

Your idea is awesome — I get it. But focusing too much on your product, instead of what your customers need, will ruin you. So work only on those ideas that will make your customers happier — not on your personal pet projects.

5. Putting off company culture

You’ve heard that company culture is important, but are you prioritizing it? The longer you wait to establish a foundation for the culture you want to build, the harder it will be to build it.


6. Not seeking a mentor early on

Mentors will help you overcome some of the most brutal and seemingly insurmountable problems you’re going to face as an entrepreneur. The sooner you get one, the fewer mistakes and pitfalls you’ll run across.

7. Holding on too long

It’s easy to take everything “personally” as an entrepreneur, from holding on to tasks as a point of pride to refusing to abandon your original ideas. But don’t be afraid to let go. Negotiate. Compromise. Delegate. Letting go is hard, but it’s often the only choice.

8. Not asking for (or listening to) feedback

Face it: You aren’t a perfect entrepreneur, no matter how much experience or knowledge you’ve acquired. There’s always room to grow, and the people around you are the best resources you have to understand how.

So, invite your team members to provide feedback on how you do business, and really listen to what they have to say.

9. Not taking enough time off

Too many entrepreneurs have allowed their personal lives to decay due to their relentless focus on building the business. They work 100-hour weeks, sleep at the office and dedicate all their free time to doing more work.

They get a lot done, but at a significant cost. So, pay attention: Unless you take regular time off, you’ll suffer physical and mental health issues, and may even experience burnout.

More from Entrepreneur:

Bono Regrets Putting U2’s New Album in Your iCloud Library

The 5 Biggest Regrets Entrepreneurs Face

What 9 Successful Entrepreneurs Wish They Had Done Differently

10. Neglecting to live in the moment

This is potentially the most significant regret on this list, because it’s the one that stays with you the longest. Entrepreneurship is an amazing journey, but it’s easy to get wrapped up only in the destination.

You’ll focus so much on getting more revenue or selling the business that you’ll forget about the little moments, like bringing the team together or celebrating major milestones along the way. Cherish those moments.

If you’re developing your own business plan, or if you’re already in the midst of building your business, there’s still time avoid these regrets. Most of them are hard to detect and subjective in nature, but trust your instincts and remember that this is a once-in-a-lifetime experience for most people. You have to make the most of it, both for your business’ performance and for your own mental satisfaction.