#133 🧭 The Shame of the Shoulds

Welcome to Tech Atypically 👋, your weekly blog for navigating the challenges of ADHD and being in the tech industry.

I am an ADHD and product management coach, helping you change one belief and take one action each week.

Part 12 of the Things I Wished I Knew Sooner Series

Belief: I should have just picked one thing.

Reality: I wasn’t unfocused — I was practicing my values before I even knew what they were.

Action: Find your core values — they'll connect the dots on a life that already makes sense.

Welcome back to Things I Wished I Knew Sooner, a series about being diagnosed with ADHD late in life.

A few years ago, a friend of mine — an ADHD PM in tech, around my age — once said something that stuck with me: we’re both late 30-something year olds with the titles of late 20-something year olds.

I laughed. And then felt shame.

I’m in my 40s now. I’m a senior program manager at a fintech company leading a nine-figure budget. And I still occasionally look around at colleagues younger than me with higher titles and more money and feel the pull of that question: had I just picked one thing, would I be further along?

For years, the answer I gave myself was yes. And that, yes, carried a lot of shame.

Here’s a partial inventory of who I’ve been:

• Thai Kickboxing instructor, professional fighter, and scholar

• Published neuroscience researcher

• Fulbright Scholar to Thailand

• Professional photographer in beer and alcohol

• Beer festival founder and owner

• Sales engineer, analytics

• Business intelligence engineer

• Product manager (since I was a bad engineer)

• Program management operations

• ADHD and product management coach

• Whiskey company co-founder

And those are just the ones that stuck.

When I look at that list without context, it looks like someone who couldn’t commit. Someone who chased novelty, jumped ship, never built deep enough in any one direction to really matter. It looks like I was always running from something.

My mom had a version of this critique she delivered regularly: why can’t you just do one thing —you’re just like your father. You can’t grasp one thing. It was meant to hurt. It did.

(She was really asking me why I wasn’t a doctor yet)

And for a long time, I internalized it. I looked at friends who had stayed in one lane — directors, VPs, people clearly further up the mountain than me — and felt shame. Not just envy. Shame.

Like my choices were evidence of a failed human who couldn’t focus their life. Someone couldn’t just work a little harder and “make it” at one thing.

It felt like reciting the story of my life was a confession of failure.

One of the most important books I’ve read is Dare to Lead by Brené Brown. In it, she defines values as

“a way of being or believing that we hold most important. Living into our values means that we do more than profess our values — we practice them.”

I didn’t read that book looking for how to tie my life together. But somehow it did.

When I did the values exercise — narrowing a long list down to just two — I landed on curiosity and inclusion.

And suddenly, the chaos made sense.

Curiosity is why I’ve moved across so many domains. It’s not that I couldn’t commit — it’s that I genuinely love learning new things, new industries, new ways of thinking. Neuroscience, kickboxing, crypto, analytics, photography — these weren’t random. They were me, being fully myself, following what genuinely lit me up.

Inclusion is why I coach. It’s why I co-founded a whiskey company in an industry that has historically been very specific about who it welcomes. It’s why this newsletter exists — to make sure that neurodivergent people in tech feel seen and not alone. Every time I’ve started something, I’ve been trying to open a door for someone who wasn’t sure they were allowed in.

I wasn’t making erratic choices. I was practicing my values — whether I realized it or not.

That realization didn’t just reframe my past. It released me from it. The shame of the shoulds — I should have picked one thing, I should be further along, I should have what they have — started to lose its grip. Because when I looked at my life through the lens of my values, it didn’t look like chaos anymore. It looked like consistency.

Theodore Roosevelt said it best: comparison is the thief of joy. I had been robbing myself for decades.

Brené Brown’s values exercise is simple and genuinely useful. You can find it at brenebrown.com/resources/dare-to-lead-list-of-values. The instructions: review the full list, and narrow it down to just two. Not ten. Not five. Two.

The constraint is the point. Most of us can name things we care about. Fewer of us know what we care about most. That’s where the clarity lives.

• Start with the list. Circle everything that resonates. Then circle the ones you can’t let go of. Then ask yourself: which two, if I lost them, would make me feel like I’d lost myself?

• Use your values as a lens on your past. Once you have your two, look back at your major decisions — career moves, hobbies, relationships, side projects. Do they connect? For most people, more than they expected, the answer is yes. That connection is what replaces shame with coherence.

• Use your values as a filter for what’s next. Before you take on a new role, a new project, a new commitment — ask how it lets you practice your values. If it doesn’t, that’s useful information. If it does, you can move toward it with confidence rather than guilt.

Shame still shows up for me occasionally. But now when it does, I treat it as a signal — not a verdict. If I’m feeling the pull of I should be further along, I ask: am I actually drifting from my values right now? Usually, the answer tells me what I’m really feeling. The shame has become the compass of my fear instead of my captor.

I haven’t climbed as high as I could have on any one mountain. But I’ve scaled a lot of different ones. And when I’m honest with myself, I know that staying on just one would have made me miserable.

My values wouldn’t have let me.

Curiosity and inclusion aren’t things I chose to care about — they’re things I’ve always cared about, long before I had language for them. The Fulbright, the photography, the coaching, the whiskey company — none of it was unfocused. It was me, practicing who I am.

In an era where AI is reshaping what tech careers look like, I’ve found unexpected comfort in this. The fact that I’ve never stayed in one lane means I know how to learn. How to adapt. How to walk into a new domain and find my footing. That’s not a liability right now, it’s a necessity.

I wish I’d known sooner that my life made sense. It would have freed me from decades of shame I didn’t need to carry and that mid-life crisis I had in my 20s.

God, I hope I don’t have another one in my 40s.

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