Skip to main content

How to Avoid Becoming a Miserable Entrepreneur

I sometimes meet entrepreneurs who are successful, but absolutely miserable. For most, they just aren’t passionate about the thing they are doing. Here are three ways that I see entrepreneurs get off course:

Author: Jeremy Harrison

April 28, 2015

I sometimes meet entrepreneurs who are successful, but absolutely miserable.

Many aren’t miserable for lack of success. One of the most miserable entrepreneurs I know is bringing home seven figures year after year. Their misery is all about mis-alignment and lack of purpose. For most, they just aren’t passionate about the thing they are doing.

The more their businesses grow, the more these entrepreneurs feel stuck.

Last week, I wrote about “3 Keys to Discover Your Calling” and shared how three factors: influence, strengths and passion play a role in finding our calling. When all three are aligned, it’s a great feeling.  But even when just one is out of whack, your work can start to feel like a prison sentence.

It may come as a surprise to think that entrepreneurs have this problem too.  After all, aren’t entrepreneurs supposed to have freedom and flexibility?  Wasn’t there some driving force leading them to start their own thing?

I think this often gets romanticized. In reality, entrepreneurs can get mis-guided and out of alignment. And once the business is up and running, it’s just as hard to break out of it as it would be for someone to leave their 9-to-5 job and go out on their own.  In fact, if that business has employees, it’s even harder because now a change doesn’t just affect the entrepreneurs, it affects the employees and their families too.

3 Pitfalls That Could Make You Miserable

Very few people intentionally make themselves miserable. It’s a process of decisions (or more often, lack of decisions) that lead people there. Here are three ways that I see entrepreneurs get off course:


Some people start a business based on an opportunity to make a lot of money, but later realize they aren’t passionate about the work.  Cash is the easy part. If you are driven by making a certain amount of money, there are numerous ways to get there. But be warned.  When you get there it won’t be enough, and so you will continue to want more and your misery will grow.  Make sure there is purpose and passion behind your work.


Some people start a highly-focused business that aligns with influence, strengths and passion, but before long money gets tight. They don’t want the dream to die, so they start compromising and taking on work that doesn’t align to pay the bills.

To an extent, many startups have done this.  If it happens a few times early on, that’s normal. But if you get hooked on the cashflow created by these other areas, you can get distracted and permanently pointed in the wrong direction. 

Lead your business. Don’t let it lead you.


This person loved their work as a “technician” before they went into business on their own, but hate the work that comes with leading and growing a successful business. 

The technician is really good at a technical skill like fixing cars, doing graphic design, making cupcakes, doing landscaping or writing software. Everybody tells the technician how great they are at their skill, and before long they start their own business. This is great for awhile, but as demand grows, the owner of the startup must hire some help. This is when it gets tough because they can’t spend as much time doing the technical work that they love, and that sucks the joy out of their work.

Let me be clear: most businesses (mine included) are started by someone who excelled at technical work. When you first start a business, you must be able to do the technical work. But if you want to grow the business beyond a solo act, you need to be willing to train others in the technical work and do far less of it on your own.  More importantly, you must enjoy leading people, building systems and setting vision, because this can only come from the top.

If this sounds like pulling teeth, you might be setting yourself up to be miserable. Michael Gerber talks about this in his best-seller “The E-Myth Revisited.”  If you haven’t read this book, order it today. It’s truly a must-read for any entrepreneur, and the most important book I’ve read since starting my company.

How to Discover Your Calling As An Entrepreneur

If you have that bug to run your own business, you aren’t alone. This exercise will help you get focused on work that can be fulfilling long-term for you.

Steps #1 – #3 come from my previous article, which you can read here.  Step #4 – #5 is unique to entrepreneurs and startups. 

  1. Step One: Identify Areas of Influence

  2. Step Two: List Your Strengths

  3. Step Three: List Your Areas of Passion

    But let’s add two more steps to this process…

  4. Step Four: Identify Real Needs
    Circle back to your “Areas of Influence” that you listed in Step One. Ask yourself, “what do those people NEED?” If one of your areas of influence are working moms, what do working moms need?  What problems do working moms face?  What keeps working moms up at night? If you listed 6 areas of influence… 6 people groups x 10 needs each = 60 possible needs / problems / pain points.  It should be quite a list.
  5. Step Five: Look for Connections Between Their Needs and Your Strengths & Passions
    Any successful startup solves a real problem in a unique way. Take a look at that list of needs, and review your list of strengths and passions (from Step Two and Step Three).  You’re looking for ways you can…

…address a real need…

… a need of people with whom you’re naturally influential…

…in a way that connects with an area of passion for you…

…while utilizing your strengths. 

THIS is the sweet spot. If you can figure this out — and it will take time and experimenting — you will be successful, while doing fulfilling work that aligns with a sense of calling.  

You can’t fake this stuff. 

If you aren’t passionate about what you’re doing, people will know.

But when you’re operating in this sweet spot… when you’re passionate about what you do, good at your work and working with people that you naturally connect with, people will be drawn to that. 

Now, go make it happen!

Get A Quote

Please answer a few quick questions and we will get you connected with a Spire Account Manager.