Here are three different routes to consider, each with their own risks and rewards.

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May 19, 2021 4 min read

This story appears in the June 2021 issue of Entrepreneur. Subscribe »

Q: I run a small business, but a big company just offered me a great position with more money than I’m making now. What do I do? — Elizabeth, Seattle

It’s ironic, isn’t it? Entrepreneurs love being their own boss — but because they’re action-oriented, big-thinking, hardworking people, they’re also the kind of people employers want to snatch up.

Of course, it’s nice to feel valued. While that doesn’t make your decision any easier, it is a good foundation to build from: No matter what, you won’t mess this up. I’ve been in your situation several times, and I’ve tried three different approaches. Here’s how you can figure out what’s best for you. 

Option 1: Stay with your business.

A few years after I started Born Fitness and Pen Name Consulting, a Fortune 50 tech company asked if I would help lead a new business venture. I loved my companies, but the offer was enticing and came with a flashy title and a big salary, so I heard them out.

Related: Why Leaving Your Job Could Be the Smartest Career Move You’ll Ever Make

During in-person interviews, I met with eight different people — and I asked each of them the same two important questions: What would success at the company look like, and what would be the initial focal point of my first six months on the
job? All eight people had different responses. When I asked questions to clarify, there was friction. That was all I needed to hear.

If you know yourself well, then you’ll know how you thrive — and when you get frustrated.

The interview process helped me see my future at this company, and it wasn’t bright. The joy of running your own business is that even if you don’t have all the answers, you know what you’re focused on and what success looks like. If these are variables you value, then go wherever they’re guaranteed.

Option 2: Join the other business.

I was recently asked to be a founding member of the nutrition company Ladder. Despite owning several businesses, I was enticed by investors who offered me a piece of the startup and a chance to build something new. 

Related: How to Quit Your Job the Right Way

I asked myself four questions: 1. Why was I interested? 2. What would happen to my existing businesses if I took this job? 3. What was the upside and downside in best- and worst-case scenarios? 4. What might I regret by passing…or accepting?

Question number two was the trickiest because I wasn’t ready to let any of my businesses die. But I found a way to change their infrastructure so I could step away. With that settled, the answers helped me make my decision: I said yes to Ladder.

Option 3: Do it all.

“The rules” say you can have only one job. That’s a dumb rule.

If you know you can bring value to another business without it affecting your own operation, then it’s worth seeing if you can provide that value while still growing your entity. (But don’t be delusional — it will certainly impact the time you have.) 

Related: How Leaders Can Inspire Their Teams to Think Bigger

If a potential employer isn’t interested, you can always pivot to option 1 or 2. But there’s nothing to say you can’t destroy the boundaries established by others and create an outcome that is most desirable for you. As I love telling my two young boys: You never know what you can do until you try, and you don’t know what’s possible unless you ask.

If you can recognize and assess your options, you’ll see this is a big opportunity and a rewarding decision. Good luck!

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