The Question Every Entrepreneur Hates

Several years ago, I quit my job as an employee in order to become a consultant or “freelancer”. As many creatives do at some point in their career, I needed to blaze my own trail and fulfill the dream of being my own boss. Armed with the independence and fortitude that often got me in trouble as an employee, I was eager to build a business on my terms.

And that’s just what I did.

Under the fabulous name of “Schwanke Marketing” (creative, I know), I slowly built a network of referrals, which led to marketing consulting contracts and creative work. And that work led to more work.

I controlled my schedule, but realistically, I was working more than I ever had in my life — because I loved it. And business was going great.

But around the 12 to 18-month mark, people started asking me the question that every entrepreneur hates.

“Are you still doing that thing?”

I was puzzled. It wasn’t just from one person. I noticed it coming up with increasing frequency. And from different people.

“Um, yeah. You mean the consulting thing?”

They’d just smile.

“Yeah, that thing….are you still on your own?”

I smiled back, confidently.

“Yeah, I am. Why?”

They never really had a reason. But they seemed so insistent on asking. So I decided to dig a bit deeper.

At the time I had a friend who had moved from agency to freelance designer, and he was experiencing much of the same.

Why this question? Why now?

It turns out that 1–2 years must be some sort of threshold for “being on your own.” It’s make or break time.

What self-employed individuals often discover is….“freelancing, consulting, or being an entrepreneur” is rewarding. But it’s difficult because you’re no longer just “perfecting your trade” — there are a lot of extras that come along with paving your own way.

Sure, you have the independence of creating your own schedule and doing business on your terms. But now you have a new boss. Or a new SET of bosses. Those are called Clients. Receivables. Invoices. Taxes. Books. Sales.

What you thought you were going to do was build a career doing the thing you love. And then you realize that the thing you love comes with all these things you don’t love. In your former life as an employee, someone else did those things.

Your new life now contains functions like selling, bookkeeping, collection calls, managing expectations, taxes, and more.

I love the game of business and marketing. And thankfully, marketing is what I do. But marketing and business go hand in hand. I readily accept the challenge of these “side jobs”, knowing that the goal is to delegate and grow.

For many people though, they quickly realize their dislike of the not-so-glamorous side of self-employment is a strong sign they should go back to a job working for someone else.

Which is why people feel compelled to ask you the question.

“Are you still doing that thing?”

The question haunted me. Why didn’t anyone know I was building a company?

Nevertheless, the question forced me to take action. And what I learned in that moment is what I now tell every entrepreneur, business owner, and marketer:

We all live busy lives.

We have thousands of connections on any given social media platform — how can we be expected to keep up with people in a way that really matters?

We can’t. #facepalm

It’s up to us to kindly educate friends, clients, associates, acquaintances, and contacts about what we do. To show, tell, and share — in a way that makes the world a better place. Not just a place that’s overrun with people talking about themselves. We have enough of those people already!

Everything and everyone are vying for our attention. Starting something has never been easier. It’s the ‘sticking with it’ that’s hard. No wonder we have more one-hit wonders than ever before.

It’s not about standing out. It’s about being consistently valuable.

It’s showing up each day in a way that’s unique, memorable, and helpful.

When you’re intentional about telling your story, you’ll see the needle start to move.

Stop expecting others to stop and watch you. It’s your job to reach out and deliver value.

A couple of years ago, when I got asked the dreaded question — “Are you still doing that thing?” — I knew I had to take action. I slowly transitioned my “consulting” company to a marketing agency under a new brand name — Simple Strat. I began building a team and creating an entity that was much larger than myself.

As the founder of a marketing agency, I still have to tell my story day in and day out. I have to take my own medicine.

And if anyone asks me, “Are you still doing that thing?” — I realize I still have work to do. And I gladly accept that.

What about you? Are you still doing that thing?

Let the world know.

Founder of and Host of HubSpot Hacks on YouTube.