Hi {{first_name | friend}},
Last week, Sara and I ran speed coaching sessions at the Button conference to help people work through whatever had them feeling stuck.
The prevailing mood: uncertainty.
Some people talked about their struggles to find new jobs—say, after taking a long pause, or with a resume full of contract roles, or at a certain age. Others brought up issues at the jobs they have—from being stuck in the weeds to pushing back against aggressive colleagues to feeling like their entire discipline’s reputation sat on their shoulders.
In so many of these sessions, under the surface the same question bubbled: how long am I supposed to wait for things to work out?
Since then, I’ve been thinking a lot about how much waiting we’re all doing right now. Crossing our fingers waiting for things to get better—for the job market to rebound, or a manager to recognize us, or the imposter syndrome to lift.
Or holding our breath waiting for things to get worse.
In these conversations, there’s nothing I want more than to give a genuine forecast. The market’s gonna turn around in Q1! Your team just needs a few more months to gel! We just gotta get through the next three years!
But I don’t have these answers. No one does.
What I do know: when uncertainty erodes your faith in yourself, you owe it to yourself to push back on that with all your might.
So if you feel like you’re on hold—waiting for things to fall into place or the chaos to end—here’s what I want you to ask yourself:
When have I survived uncertain times before? You don’t need to look outside yourself for wisdom—you’ve got plenty in reserve from all the times in your life you’ve taken a risk or stepped into the unknown. What helped make that process bearable—maybe even transformative? Remembering these moments reminds you that you can get through uncertain times again.
What rules am I following that aren’t serving me anymore? We’ve internalized that there’s one road to “success”—and it looks like a tidy, straight vertical line up. And when our lives don’t look like that, it feels like we’re failing. But whose path has ever looked like that, really? Now, more than ever, challenge yourself to think critically about what you “should” do.
Where can I draw inspiration? Just as remembering times you’ve gotten unstuck helps you believe you can do it again, so does looking to others’ journeys. Who’s taking a different route that you can learn from? Maybe it’s the designer who started their own small consultancy, or the peer who took leave to take care of their burnout, or the colleague who started speaking up more in meetings. What can you learn from them?
How can I make meaning right now? Maybe you can’t game out your next 10 career moves right now—but what can you optimize for today? Maybe it’s to be a little playful in an awkward situation, or a little bit bolder in a tense interaction, or just a little bit kinder to yourself. I bet there’s something you can be proud of yourself for every day—standing up for a colleague, or helping out a laid off friend, or even getting enough sleep. Take the wins now.
Even in times of transition, your life is still… your life. Yes, there is plenty that’s out of your control. But you are not on stand-by, idling while you wait for things to click into place. When forward momentum feels stalled, there’s still plenty of good to do right where you stand today.
—Jen
Let’s write design’s next chapter.
January 29-30, 2026 • Online
Two days. Zero nonsense. Just brilliant talks and workshops from…
Erika Hall | Ron Bronson | Candi Williams | Catt Small | Pavel Samsonov | Margo Stern | ÌníOlúwa Abíódún | Lisa Woodley | Shawna Hein | Ida Persson | Hang Xu | Farai Madzima | Amy Santee
The first 75 tickets before November 10 are just $299. Snag yours before they run out.
Registering a team? Save up to 60% off the individual price with a team pass.