What If This Is Success?
Redefining "enough" (+ a check-in template to help you figure it out)
Working for yourself means there are no promotions. No performance reviews. No celebratory messages in the #general Slack channel to announce you’re doing a great job.
Which means you get to—and have to—decide when you’re succeeding.
And that can feel... wobbly. Confusing. Weird. Hard.
As we brainstormed this post, we noticed something interesting: Now that we work for ourselves, we feel confident in our personal lives—raising kids, building community, designing days that feel good.
But when it comes to professional success? It’s murkier. There are fewer milestones. Fewer gold stars. Fewer obvious markers of an impressive career.
Even though we’ve built businesses that support our families and our lifestyles…
Even though we’ve led client work we’re really proud of…
We sometimes still feel like we haven’t done enough.
This whole post started on a catchup call (as many of our best ideas do).
We were mid-conversation, trying to put words to this exact feeling—that working for yourself can be wonderful and weirdly hard to validate. And then we realized: “Wait… this is success. We just need to say it out loud more.”
Before we started writing, we each took time to journal about how our definitions of success have evolved. If you're curious to hear how that conversation unfolded, you can listen in here:
And then, we came across this quote from Justin Welsh (an excellent Substack follow, by the way). It put into words what we’ve been trying to live out:
“Most people build their career first, then try to fit their life around it.
It’s part of the reason why everyone's so exhausted and empty.
It’s much harder, but I’d recommend designing the life you want, then finding work that funds it.”
That one hit us hard—and summed up exactly why we’re building The New HQ. Why we’re so passionate about helping people* define success for themselves, not just once, but over and over again.
*(And yes, “people” includes us. We need the reminder, too.)
A 5-Minute Monthly Success Check-In
But how do you actually do the work of defining success? (Yet another thing they didn’t teach us in school.)
Just because we work for ourselves doesn’t mean we have to do it all alone. We’re lucky—we’ve chosen each other as colleagues on this independent work journey. And over time, we’ve learned that one of the most valuable habits you can build is surprisingly simple:
A short, honest check-in.
Just five minutes (we timed it for you!) to look back at what worked, what didn’t, and what you want next.
This practice is inspired by a template originally shared by Amber Rae, and it’s become a wildly contagious habit. We’ve pulled more than a few friends into the monthly check-in club.
You probably already track revenue or invoices. But what if you also tracked your learnings? Your growth? Your boundaries? The important-but-not-captured-in-a-resume wins no one else sees?
That’s what this check-in is for.
It’s not just a feel-good exercise—it’s a smart business move. It helps you recognize progress, surface insights before they get buried, and realign your goals with the season you’re in. Over time, you start to notice patterns: what drains you, what fuels you, and what success feels like—not just what it looks like on paper.
Monthly Success Check-In Prompts
Once a month, take five minutes to answer these questions. Do it solo—just jot them down in your Notes app so you can look back later. Or even better: screenshot the prompts (or copy the graphic) and text them to someone you trust. Hold each other accountable. Be each other’s cheerleader.
One moment I felt successful last month was…
Something I’m proud of that no one saw was…
This month, I want to feel more…
Success right now looks like…
I’m giving myself permission to let go of…
If I get stuck, I’ll remember…
Redefining success starts here. It’s a simple habit—with a wildly outsized impact.
Want to do it together? We’re trying something new, and hosting a (free! but limited spots available) Month-in-Review Session on Wednesday, August 27th. Learn more + RSVP here. It’s an accountability call to review the check-in together with the goal that you’ll leave grounded, clear, and maybe even feeling… dare we say it… a little bit more successful.
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Will be at next month’s checkin! Such a good idea.