Get All Access for $5/mo

Is That Dream Opportunity a Nightmare Waiting to Happen? Don't let fear of missing out stampede you into an opportunity that isn't the right fit.

By Dixie Gillaspie Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


A week or so ago a long-time client asked me to review an opportunity one of her business partners had sent her way. In her email she said she was excited. When we got on the call for our session it was clear that she had some reservations.

The plan they'd presented to her was solid. I found a few potential problems and areas she needed to clarify, but there were no significant red flags, except that she was trying too hard to convince herself that it was something she wanted to do. If there is anything I've learned about entrepreneurs it's that the shortest route to self-sabotage and failure is a great business plan for a business we don't really care anything about.

But "I have a business idea I think is perfect for you," is to an entrepreneur what free pens and other gadgets are to conference goers. It's not like we don't have enough ideas (or pens and other gadgets) or that the ideas offered by others are really superior to our own ideas. No, it's just that feeling if we don't jump on board with this idea, right now, we'll end up being a legend like Ronald Wayne – the third co-founder of Apple Computer who sold his stock in the company for $800.

But the truth is that none of the founders could have guessed that Apple was an idea that would someday be worth what it is today. While theoretically he missed out on billions, he has gone on record as saying he doesn't regret the decision he made because he made "the best decision with the information available to me at the time."

I suppose it's possible that my client will someday discover that she's turned down an opportunity to be part of something worth billions. But after deep analysis, neither of us think that's likely. What we do think is that she would have been trapped into a position with a startup company that has potential, but would have made her miserable long before it made her wealthy.

Here are the five questions I had her answer that led to her decision.

1. Will you work with the people you want to work with?

Wayne has said that he chose not to return to Apple because he felt that working with the other two partners was like "having a tiger by the tail." My client didn't describe her prospective partners in quite the same way, but she quickly volunteered that she enjoys them as friends and has a lot of respect for their talents and experience, but doesn't like the way they treat each other. Their dynamic is abrasive and she felt that they would build their company with that same culture. The target market for this business isn't a demographic she enjoys serving so she wouldn't be working with her dream clients either. No redeeming points on that question.

Related: Say 'No' to These 5 Things for an Immediate Life Improvement

2. Will you spend your time and energy on tasks you enjoy doing?

Here my client had to say she was torn. She was being asked to step into a role that would allow her to do almost exactly what she is doing in her business now. The problem is that she had already confessed to me that she is bored with what she is doing. The reason she is entertaining new business ideas is that she thinks she is ready for a challenge. We ended up calling this a tie since it would be an easy transition for her, but not sustainable or satisfying in the long run.

3. Can you leverage your core talents for more compensation that you could have elsewhere?

This was a huge light bulb moment for her. While the role she'd be taking on would allow her to stay in her comfort zone, it wouldn't give her the opportunity to leverage her research skills and that is the areas where she stands head and shoulders above most of the people in her field. And it would mean an initial pay cut. This got a big "no."

Related: Base Pay vs. Recognition: What's More Important?

4. Does this dream opportunity require risks you can't afford?

This was another point that Wayne made about his lack of regret over his decision. He was, at the time, worth more than his two partners and he had significant personal assets that potential creditors could take if the company didn't meet their obligations. That represented an unacceptable risk. My client and I worked through the proposed agreement and there was no real risk involved except the loss of clients and momentum in her own business if the enterprise failed. But it's a question everyone has to consider before embarking on any new venture.

5. Will I be proud to be associated with it?

This came back with another tie vote. Yes, she'd be proud to be part of a successful startup, but she wouldn't take any particular pride in being part of this one.

Ultimately, she decided that she had nothing to fear about missing out on this opportunity. It might be a dream opportunity for someone, but it wasn't her dream even if it came true.

Related: 14 Early Startup Execs Who Missed Out on Making Millions

Dixie Gillaspie

Writer, Coach, Lover of Entrepreneurship

Ever since she was a little girl, Dixie’s least favorite word was "can’t." It still is. She's on a mission to prove that anything is possible, for anyone, but she's especially fond of entrepreneurs. She's good at seeing opportunities where other people see walls, navigating crossroads where other people see dead ends, and unwrapping the gifts of adversity and struggle. Dixie also contributes to Huffington Post and is a senior managing editor for The Good Man Project.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick


How to Close the Trust Gap Between You and Your Team — 5 Strategies for Leaders

Trust is tanking in your workplace. Here's how to fix it and become the boss your team needs to succeed.

Health & Wellness

Get a Year of Unlimited Yoga Class Downloads for Only $23 Through June 17

Regular exercise has been proven to increase energy and focus, both of which are valuable to entrepreneurs and well-known benefits of yoga.

Growing a Business

He Immigrated to the U.S. and Got a Job at McDonald's — Then His Aversion to Being 'Too Comfortable' Led to a Fast-Growing Company That's Hard to Miss

Voyo Popovic launched his moving and storage company in 2018 — and he's been innovating in the industry ever since.

Business News

'Passing By Wide Margins': Elon Musk Celebrates His 'Guaranteed Win' of the Highest Pay Package in U.S. Corporate History

Musk's Tesla pay package is almost 140 times higher than the annual pay of other high-performing CEOs.

Starting a Business

I Left the Corporate World to Start a Chicken Coop Business — Here Are 3 Valuable Lessons I Learned Along the Way

Board meetings were traded for barnyards as a thriving new venture hatched.

Business Culture

Why Remote Work Policies Are Good For the Environment

Remote work policies are crucial for ESG guidelines. Embracing remote work can positively impact your business and employees.