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Coping with impostor syndrome

While discussing impostor syndrome with friends recently, I was shocked to realize that for me it had mostly…gone away??? So much of my career has been plagued by (often very painful) feelings that I’m no good, and sooner or later everyone else will figure that out too. This current state of freedom would’ve been inconceivable.

That got me thinking about what helped inspire this change. I found this came down to three basic strategies:

  1. Recognizing the good in discomfort
  2. Getting in the reps
  3. Documenting evidence of personal growth

Note: in my experience, marginalization-based impostor syndrome requires an additional set of strategies, and these may be more deeply personal or individual. This blog post is focused solely on the strategies I’ve developed for dealing with feelings of “insufficient” skill.

Recognizing the good in discomfort

Way back in 2013, I shared this quote from Ira Glass:

Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you.

I wish I had internalized this earlier, because it’s true: your frustration is telling you that you have a good sense for quality, and you know you’re not there yet. This is something to be celebrated! You have a target to move towards, and you can trust your judgement to guide you closer to where you want to be.

Getting in the reps

Patience with our evolving abilities is hard, though, so pairing the internal work with action can help. I found the best way to grow my skills is to get in the reps, and to be intentional and specific about the skills I’m trying to build. I do this in 3 steps.

Step 1: get specific on what I’m “not good at”

What specifically is bothering me about my work? Have I heard any thematic feedback about these projects? Could I ask for that feedback? What limiting beliefs do I have about my work? Which of these do I wish weren’t true?

Examples for a product manager might include…
  • My written communications tend to be verbose (hi, it me)
  • I don’t know how to run effective correlative analysis
  • My market research isn’t as systematic or structured as I’d like it to be
  • I don’t talk to customers frequently enough

Step 2: pick one skill to develop during my next project

I might choose by what’s bothering me most, or what opportunities are currently available. Often I’ll dream up a personal project to learn something new, or find a low-stakes opportunity at work. Lower stakes can grant us additional psychological safety when building a skill.

Example: I’ll work on brevity in communications for the duration of my next roadmap initiative.

Step 3: do the work!

In the brevity example, I might…
  • Research and apply frameworks for clear, concise messaging
  • Set a word limit
  • Imagine the audience is reading my message on their phone (thanks for that 🔥 tip, Joel!)
  • Practice getting words down in a first pass, then editing for brevity and clarity

I’ve found it helpful (for some tasks) to focus on generating as many options as possible within a timebox. When I’m in pursuit of volume, I 1) don’t have the mental bandwidth to spiral and 2) am more likely to stumble upon a compelling option.

If my brain does get yelly again, I can redirect it back to my intention for the project:

Thank you, brain, for trying to protect me. But right now, what this project needs is a brief Slack message that will prompt stakeholders to review the product requirement doc by the date requested. Hmm, what if I try “signposting” techniques here?

Objectively centering what the project needs, instead of my own “shortcomings”, has helped me take the heat out of these frustrations. I think this would be even more powerful if I were to write my intention down at the beginning of a project:

For the Flimflam integration initiative, my intention is to practice crafting clear, concise internal communications.


Repeat this process enough times and you might find that your “weakness” becomes a strength. My brother, a sequential artist, used to say he wasn’t good at background design. He practiced by drawing a LOT of backgrounds…and then a gaming company hired him to do exactly that, full-time.

Documenting evidence of personal growth

Take note of daily wins

At the end of each work day, I write down 1-3 personal wins from the day, no matter how small. I later highlight 3 favorite wins in my weekly review. Attention creates our reality, and so I find this practice makes continual progress more obvious.

Keep a “brag sheet”

At the end of each two-week sprint, I tend to my brag sheet (Julia Evans has a good write-up on brag documents).

What goes in my brag sheet
  • The opportunity we were solving for and why
  • The goals and solution
  • My role, including special contributions
  • Specific learnings
  • Outcomes, including success measures and feedback

This format is very easily to translate to annual performance reviews and “STAR”-style interview stories. Importantly for impostor syndrome, it’s also a growing body of evidence that I’m becoming more effective at what I do.

These brag sheets are very satisfying to look back on: it’s amazing what we actually accomplish over time!

Keep an “encouragement” document

While internally-sourced evidence has been most effective in building confidence and self-trust, external validation doesn’t hurt. I keep an “encouragement” document where I file any positive feedback I’ve received regarding my work or my character. If I’m having a rainy day, it can be really nice to glance through that document. Just seeing how short the scrollbar thumb is getting is quite gratifying.

The encouragement document also helps me find patterns and pinpoint my strengths. I recently realized: “oh, caring is actually my superpower” (great news for a person who Feels their feelings).

The corollary here: it’s just as satisfying to liberally share genuine gratitude and appreciation for the people around me!

A note on transferable evidence

Several years ago, I made a career switch from web design-and-development to product management. Everything I learned in my designer trajectory shapes who I am as a product manager today.

Please don’t discount transferable knowledge: all your past accomplishments “count”. Your time working in retail “counts” towards your ability to talk to customers. Your self-initiated web projects “count” towards your grasp of technical concepts. It. All. Counts.

My impostor syndrome story

Over the years, my impostor syndrome has mostly dissipated thanks to recognizing the good in discomfort; getting in the reps; and documenting evidence of personal growth.

I’m sure impostor syndrome could return in significant “stretch” periods, but I’m now feeling more confident to handle it when it does. I hope my story helps you find strategies to try, and I’d be curious to learn what else has worked for you!


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