To Entrepreneurs Who Are Doing the Work Because You Think You Have To

By: Cindy Free

If you don’t have anyone on your team with a driven, proactive, self-motivated, raise their hand, helpful, entrepreneurial mentality, it’s time to hit pause, reset, develop a new strategy, and rebuild your team.

You’re an entrepreneur. You need a high-functioning team that’s willing to roll up their sleeves—just like you—and get the work done. That way, you can focus on your true value: doing what you love, and doing it with excellence.

The Quadrant Exercise for Entrepreneurs

I recently had the pleasure of participating in an exercise with a group of fellow entrepreneurs, led by my colleague Eliot Wajskol, a Certified EOS Implementer and co-founder of FiftyPages.

The Activity

We created a simple quadrant and labeled it as follows:

• Upper left – Things I love and am damn great at. (I wish I could do more of this, and I know it brings real value.)
• Upper right – Things I like and am good at. (Satisfying most of the time, but someone else could—and probably should—do them.)
• Lower left – Things I don’t like but am good at. (These tasks burn me out or make me want to scream.)
• Lower right – Things I don’t like and suck at. (My words, not Eliot’s.)

Here’s what we discovered: most entrepreneurs spend only a small percentage of their week doing what they love and are great at. The majority of our time? Spent doing the stuff we don’t like and suck at.

Why? What the heck? This is not what you signed up for as a business owner. And it’s not sustainable.

I consider myself one of the lucky ones who now spends most of my time doing what I love and do well, but it wasn’t always that way, and it won’t always be. As Eliot reminds us, there are seasons when we have to step back into roles we’ve set down or offered to others.

I also think about how leadership team members would complete this exercise. Are they focused on their greatness? Do we have the right people in the right seats, doing the right work?

Entrepreneurs, Let’s Talk About the Myths Holding You Back

Too often, business owners talk about their operational pain points as if they’re facts, but in reality, they’re just stories. Myths. Excuses we tell ourselves to avoid making decisions around hiring or developing our people.

Let’s unpack some of the big ones:

1. I can’t afford to hire someone to do these things.

That might be true today, but here’s the real talk: doing things you hate or aren’t good at (or even things you enjoy but shouldn’t be doing) is sucking revenue from your business.

Maybe it’s time to take a leap. Could you train someone internally? Split tasks across your team? You don’t always need to hire a full-time position to get help.

Also, what is your time worth? If you’re doing $15–$50/hour tasks, you are costing your business more than you realize. Spend your time updating job descriptions, creating task lists, and training people. That’s what leaders do.

 

2. I don’t have anyone who can do this as well as I can.

So what? Of course, you’re caught up in your own perfectionist loop. Get over it. Get out of your own way.

What if they don’t do it exactly like you—what if they do it better?

Being a great leader means recognizing that there are many paths to success. Set expectations, create clarity, coach as needed—but let people rise. You cannot grow if you insist on being the bottleneck.

 

3. My clients only want me to do these things.

No, they don’t. You think they do. Time for some tough love: You’re not that special. And if you truly are the only person they trust, you’ve got a leadership issue, not a client preference issue.

You want to scale? Start building trust inside your business. Train your team, delegate effectively, and stop believing you’re the only one who can do the job right. That mindset will keep you stuck in 80-hour workweeks with zero work-life alignment.

 

4. I don’t want to give up control.

Of what, exactly? (Eye roll.) Go back to your quadrant and obsess over the stuff you love and are great at. Control that.

Letting go of the rest will give you something better: a thriving, collaborative culture, diverse perspectives, and clearer paths for team growth. You are the conductor, not the one-person band.

Still want total control? Then stop planning for growth—because you’re not creating space for it.

 

5. I don’t have time to train someone else.

Yes. You. Do. And if you truly don’t, then empower someone on your team to help.

Most employees take a job because they want growth and development—not because they want to run the company, but because they want to learn more and contribute more.

People leave when they’re underutilized. I guarantee someone on your team already knows how to do something you don’t, and they’re staying quiet because they don’t think they’re allowed to speak up.

 

Entrepreneurs, want to talk more? Let’s connect.

Originally posted on LinkedIn here.