Three Years In

If you love what you do, you’ll have to fight like hell to keep doing it.

I was driving home from my office this morning after a client session when it hit me:
I’ve driven these streets before—but this time’s different.

Back in the summer of 2022, around 10:30 on weekday mornings, I’d be driving home from a work session at Tala Coffee in Highwood.

I didn’t have clients.
I didn’t have a coaching certificate.
I didn’t have an office.

I didn’t have so many things.

But I did have a vision—faint and unfinished—for what I wanted my work to look like.
What I thought I wanted to do, and what I now actually do, turned out to be wildly different in scale and depth. What I imagined was small. What it became is something else entirely.

Now, I see myself partnering with local institutions.
I’m part of a coaching network.
I coach in person. I get to be impressed by my clients.

I’ve designed my own coaching tools.
I’ve coached at industrial artists’ retreats.
I’ve traveled to conferences.
I’ve met virtual clients in their hometowns.

People shout out of their car windows in Market Square: “Hey, Coach Dave!”
I see how good I’ve become—and how much more there still is to learn.

I see how different I feel, just driving the same street three years later.

I’m using partnership marketing again—the same playbook that worked so well at my last company.

I have an intern now. Ops and Marketing help. A coaching supervisor. An ACC credential. Friends in the field.

And now, I’m starting to envision a company.
Not just a coaching practice—a full-scale coaching company I’ll build over the next three years.

I see the number of people who trust me. With their goals. Their fears. Their achievements. Their dreams. Their stories. I see the days when I feel like I know exactly what I’m doing—and the ones when I feel completely lost.

There are moments when it feels like I’m grinding.
And then others that flow—like the work is moving through me.

I see how much of me I get to be in coaching sessions, networking meetings, sales calls. And how much people want me here.

I see how a blend of curiosity, preparation, and opportunism landed me my first office in Lake Bluff… which led to the office in Lake Forest… which now fuels my desire to build a full coaching center—for this region and beyond.

I think about the sheer amount of copy I’ve written. The hours I’ve logged on ChatGPT, Canva, Notion, LinkedIn, QuickBooks, Google Docs, Gmail. And the time I will need to spend in HubSpot and SquareSpace to get where I want to go.

Plus all the coach training programs still ahead.

I still wrestle with the same gaps in my working style.
Solo work exposes your patterns.

But I’ve also become a model—for people navigating job loss, reinvention, or exploration—who want to do it on their own terms.

I’ll never be younger, greener, or more naive than I am right now.
This moment is the lowest experience I’ll ever have again.
And that’s a gift.

I see where I’m magnetic, and where I repel.
Where I’m helpful, and where I can hinder.

I see how rejection and failure no longer scare me.
They’re not just part of the process—they are the process.

I’ve also realized something else:
That old cliché—“If you love what you do, you’ll never work a day in your life”?
Yeah, no. I think it’s the opposite.

If you love what you do, you’ll have to fight like hell to keep doing it.
And fighting is work.

It’s tension. Mystery. Strategy. Timing. Risk. Practice. Defeat. Victory.
It’s violent and graceful and exhausting and worth it.

For me, the Work is work—on three levels:

• The work of running a business

• The craft of coaching

• And the constant personal work of becoming a sharper, braver, more focused version of myself

Three years in, that’s what I see.