When “do what you love” stops loving you back

Years ago, when I was trying to figure out what the hell to do with my career, a friend gave me some advice I’ll never forget:

“Follow your happiness.”

At the time, it sounded… ridiculous. Vague. Soft. Like something you'd find on a candle in HomeGoods. I nodded politely and went back to my project plans, wondering how anyone could afford to make decisions based on happiness.

But here’s the thing: I eventually did it.

I followed the work that brought me joy—work that felt useful, human, and a little rebellious. I leaned into coaching, content, and culture. I wrote Project Management for Humans to remind people that work isn’t just about tasks and timelines. It’s about people. It always has been.

Then I built a business to help teams communicate better, collaborate better, and maybe even feel better at work. We called it Same Team Partners. We have written a ton of helpful content and made things I’m proud of—like the Teamangle Conversation Cards, diagnostics, workshops, all of it.

And for a while, I was genuinely happy. Fulfilled. Energized. On purpose.

But lately… that happiness has been harder to hang onto. Not because I don’t love the work. I still do. But because the work, at least right now, doesn’t quite love me back.

The slowdown no one warns you about

Let’s just say things are... quieter than I’d like.

If you run your own business or freelance, you probably know the feeling. Inquiries slow. Budgets vanish. Projects that felt like sure things turn into silence. People are tapped out, overcommitted, and scared to spend. And no amount of personal passion can force a contract to close.

This spring, for the first time I can remember, I couldn’t take my family on a spring break trip. That’s not something I say lightly. We’re not flashy travelers, but we’ve always gone somewhere. Made memories. Unplugged.

This year, it just wasn’t in the cards—or the budget.

And yeah, it stung. Not because of the vacation itself, but because of what it represented. That even after all the years of doing the “right” things—leaving the 9-to-5, building the business, following the happiness—I’m still at the mercy of an economy that doesn’t care about purpose. A market that rewards scale over substance. And a culture that treats burnout like a badge of honor and slowness like failure.

Redefining what “making it” even means

I used to think making it meant stability.A steady pipeline. A thriving client list. Maybe a speaking gig or two. I worked hard for that. I built systems. I built relationships. I followed my damn happiness.

But the longer I do this, the more I realize: even when you “make it,” you can still feel like you're one quiet month away from questioning every choice you've ever made.

This is the part no one tells you about when they preach “do what you love.” That it can be incredibly meaningful and completely unsustainable. That you can wake up proud of your work and still feel anxious about your future. That passion doesn’t guarantee paychecks.

What I’m letting go of

I’m not giving up. But I am letting go of a few things.

• The hustle-for-hustle’s-sake mentality.
• The belief that busy equals successful.
• The pressure to always be building, always be pitching, always be “crushing it.”

I’m still building—just differently. I’m making space for creativity again. I’m writing more. Designing new offerings. Reimagining what I want this work to feel like. I’m even finding ways to make project management content more human again (yes, it’s possible).

And I’m doubling down on what I know matters: Helping teams. Helping people. Not with jargon or bloated proposals, but with practical, affordable, human-centered tools that actually make work feel better.

The wild part? That’s always been the goal. But it’s easy to forget that when your calendar’s empty and your inner critic has the mic.

If you’re in this weird, wobbly place too

Here’s what I know: You can love your work and still wonder if it will sustain you.
You can build something beautiful and still feel broken by the weight of keeping it alive. You can do all the right things and still need to grieve when it doesn’t pan out like you hoped.

If that’s where you are, I’m right there with you.

And if you're sitting with those same uncomfortable questions—about value, visibility, money, meaning—I hope this reminds you that you're not alone. You're not a failure. You're just living in a moment that doesn’t have easy answers.

Sometimes following your happiness looks like getting quiet. Rebuilding. Creating even when no one’s watching.
Sometimes it looks like helping people, even if they can’t hire you yet.
Sometimes it looks like resting.

This isn’t the post where I tell you it’s all going to be okay. I don’t know that.

But I do know this: You’re still here. You still care. And that counts for something.

TL;DR

I followed my happiness. I built a business around the work I love. And right now, it’s harder than ever. But I’m still here. Still believing in the work. Still showing up—just differently. If you’re navigating a slow season, a quiet pivot, or a loud identity crisis, I hope this helps you feel seen. You don’t have to hustle your way out of it. You’re allowed to feel it. And maybe—just maybe—happiness will catch back up.