The hardest part isn't the job search

Mar 25, 2026 8:01 am

The hardest part of being an experienced

designer at a crossroads isn't the job search.


It's asking for help.


You've been the senior person in the room. The one others come to. The one who figures it out, navigates the politics, mentors the juniors, holds the project together.


Asking for help with your own career feels like admitting the thing that made you valuable — your ability to handle things — has stopped working.


It hasn't.


What's changed is the system. The system that rewards "figure it out yourself" inside a company actively punishes it outside one. The job market doesn't reward self-sufficiency. It rewards visibility, positioning, and the right conversations with the right people at the right time.


Every single designer I've worked with — all 50+ of them — hesitated before reaching out. Most waited months longer than they needed to.


Not because they didn't know they needed help. Because asking for it felt like a statement about who they were.


It's not.


If you're reading this and feeling that tension; the tension between knowing you need to do something different and feeling like asking for help means you've failed; that tension is actually a sign of something good. It means you still care enough to hold yourself to a standard.


The market changed. What it takes to navigate it changed. Recognizing that isn't weakness. It's awareness.


If you've been sitting on a DM for a few weeks — I get it.


DM me BACKDOOR whenever you're ready. Two questions. 3 minutes. Private. No one sees it but us.


Next cohort starts March 30.

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