The Biggest Mistake of My Entrepreneur Journey (And It Was a Whopper!)

For business owners, our start-up stories sound a lot alike. In those years leading up to the self-employment leap, we were burning out on bureaucracy, bosses, and bullshit, and we were starry-eyed about what awaited us as self-made men and women. We imagined:

• Making our own schedules.
• Answering not to a tyrannical boss (but only to the clients and customers, who we were sure would be amazing and collaborative and appreciative of our efforts).
• Achieving the coveted work/life balance we had always dreamed about.
• Doing deep work (the kind Cal Newport talks about) and never being bogged down by shallow “busy work.”
• Applying our best talents to the coolest projects and feeling “in flow” all the time.
• Building brands and celebrity and our bank accounts.

We imagined much, but we often planned too little. And I can’t be alone when I admit the biggest failure of my life as an entrepreneur:

In my attempt to become my own boss, I accidentally became my own employee.

Next year, my company will be 20 years old. I am full of pride and gratitude and awe about what I have seen, accomplished, learned, and survived. But as I think about what’s to come in the next 20 years (or maybe just 10 because, well, retirement sounds pretty sweet!), it’s time I got really honest about where things stand.

As a founder and owner, I call the shots. The proverbial buck stops with me. I have a career on my own terms. I make the schedules and choose the deadlines. “Blah, blah, blah.” You see, it’s all just a story I tell myself because, truth be told, I still sometimes come to the office feeling overwhelmed, behind schedule, beholden to others, under-appreciated, under-compensated, and like I’ll never catch up. And it all comes down to one problem and one horrible state of affairs.

The problem: When I transitioned from corporate employee to business owner, I never shed my people-pleasing instincts, my practiced art of saying “yes” to everything, and my unconscious belief that other people’s needs (e.g., demands, assignments, projects, requests) are more important than mine. I never learned to say more NO and less YES. As my executive coach told me many years ago, “You’re too nice, Kate. And that’s going to be a problem.”

The sad state of affairs: I’m not a boss or a leader — not in the sense that I want to be. I’m an employee, once again, who answers not to a flawed supervisor or a dysfunctional corporate culture or a ridiculous HR code of conduct. I am an accidental employee who has inadvertently let my belief in outstanding client service result in putting myself last (just as I have always done, even since my early days as an entry-level employee).

How to Know If You’re Not Really the Boss

Take a few lessons from me, I beg of you. It might be time to reassess your boundaries, your yes/no ratio, your mindset, or your daily practices if any of the following are true:

1. You feel guilty taking the time to read this 900-word article, because you’re “too busy” and it feels selfish to invest in your own development and self-awareness.
2. You haven’t written your own blog posts or created new content that builds your brand in months – or ever. (Because that’s not what you’re paid to do, and “ain’t nobody got time for that!”)
3. Your desk is a disaster, you can’t find a pen, and you’re running late to the meetings you scheduled. (Ahem. What’s up with that?)
4. More than 20 hours of your week are scheduled with meetings, and there’s nothing on the agenda for the next seven days that includes uninterrupted time for a project that you’re excited about and that helps you and your company grow. (But I thought you made the schedule?)
5. You have clients you don’t absolutely adore, and you have no plans to cut them loose.
6. You come to your workspace each day with a head full of what you “have to do” and not focused on what you “want to do.” And all those “want to dos” are relegated to a someday/maybe folder somewhere that is beginning to feel like a “probably never” folder.

Sigh.

I’m sharing this epiphany with you for two reasons. First, because I believe that vulnerability is a strength and that honesty helps me grow. And secondly because I know that I can’t be the only entrepreneur who needs a post-pandemic mindset reset in this regard. When we know better, we do better. And I know, without a shadow of a doubt, I want to be my own boss, not my own employee. So I’m about to start making different decisions to drive different results.

If you’re thinking that I make “being an employee” sound like a drag or inferior to business ownership, that’s not my intention. There’s nothing wrong with being an employee. You can lead and grow and inspire and create value on someone else’s payroll. You can cash in on employee benefits and a subsidized retirement plan. You can love your job, every day and in every way. And you can even enjoy being led by your boss.

But if you’re a business owner who has discovered she’s actually just her own employee, it might be time to ask yourself, “Why am I paying the utilities around here?” Perhaps it’s time to finally choose: being an owner or being an employee. There’s nothing more exhausting than being both.