How I Built a Career With ADHD and No Marketable Skills
By Sean Weas
Sean Weas is a growth and product expert who has spent more than 13 years building technology companies. He was on the founding teams at GrowFlow, C-StoreAI, and Daily.ai. Find him on LinkedIn.
I’m doing that thing again: scrolling through LinkedIn job listings in a startup founder midlife crisis. Senior growth, marketing, and product roles appear on the screen, each promising a potential path forward, diverging from the startup wilderness I’ve wandered for the past decade.
Journeying back from the wilderness, I’ve had a singular goal: stability. I eagerly scan each job listing, enticed by the promise of a predictable routine, clearly defined roles, and a sense of security that comes with an established organization. Compared to the chaos of startups, the idea of a steady paycheck and a clear career path in a well-oiled corporate machine seems reassuringly stable. But the whole experiment collapses when I read the job requirements: 10-plus years in B2C in-app marketing, eight-plus years managing large marketing teams, and a laundry list of hyper-specific demands for experience that read like a corporate leader’s fever dream.
I watch the tabs flutter away as I close my browser. A familiar thought creeps in: What's the point of this search? After years of startup life—turning chaos into scalable systems, wearing more hats than a haberdashery—I've become a unique blend of experiences that doesn't neatly fit into traditional job descriptions. I'm overqualified in adaptability but underqualified on paper. I'm learning to embrace this unconventional path, recognizing that true stability comes not from a predictable career trajectory, but from my ability to adapt. It's a lesson I'm gradually internalizing.
If I’m honest with myself, these types of career paths never really appealed to me. I’ve always found it difficult to function as a smaller piece in a larger machine; having a clearly defined role of someone else’s design. Sometimes, being siloed on a predictable track sounds calming; a sacrificial trade of autonomy for consistency. But my mind is just too restless. Ultimately, I prefer forging paths in the wilderness to speeding down well-established roads.
The LinkedIn “stability search” is a symptom of internal tension between entrepreneurship and traditional employment. Startups afford autonomy but can bring hardships, while a W-2’ed role is just the opposite. To me, it’s an obvious truth: the idea of doing the same thing for eight-plus years seems incredibly boring. Until recently, I figured that stance was a personality quirk.
Adults with ADHD have a hard time hacking it when it comes to traditional jobs. Untreated, they lose 22 days of productivity a year and are 60 percent more likely to be fired than their peers.
My diagnosis came just over a year ago when I was 37, well into my meandering career path. In school, I didn’t struggle with lack of attention or being overly disruptive. I’d get bored and zone out, but it didn’t impact my academic performance. I didn’t get in trouble because of my hyperactivity. I wasn’t in detention or the principal’s office on a regular basis.
But I still felt different from my peers. I’d always had a suspicion that I had ADHD.
At the suggestion of my sister, I got tested. She was in school pursuing a master’s degree in mental health. One of her internships was with a group that focused on ADHD diagnosis. She had just been diagnosed herself, so I agreed to go in and get tested.
The interview with the psychologist lasted a few hours. It was revelatory. Nearly all of the questions they asked gave me a feeling like ‘that’s me’! I walked away understanding much more about myself, my thought patterns and my natural inclinations.
I learned that ADHD is increasingly recognized as a spectrum disorder. There are three primary presentations of ADHD:
Predominantly Inattentive Type (ADHD-PI) where symptoms are primarily related to sustaining attention, organizing, and following through. This is estimated to affect 20 to 30 percent of those diagnosed.
Predominantly Hyperactive-Impulsive Type (ADHD-PH). This manifests as impulsivity and restlessness along with constant mental activity. This is what I was diagnosed with. It’s less common, affecting five to 10 percent of those diagnosed.
Combined Type (ADHD-C). Combined symptoms of inattention and hyperactivity are the most typical presentation, accounting for approximately 70 percent of those diagnosed.
My diagnosis was like having new glasses. Through the new frame, everything in my day-to-day life became clearer. I started to notice thought patterns more closely and everything felt like it made more sense. Even though not much changed, everything looked different.
The tension I felt between what I felt I should do (find stability) and what I ultimately did (take risks) made a lot more sense. Natural inclinations, unknown to me before, were revealed. There is a good reason why I'm attracted to startup wilderness, and why getting curious and leveraging these traits has been key to my success.
Ever since I graduated with a degree in architecture, I’ve been hopping from one opportunity to the next. I never worked in architecture. Instead, I became fascinated by web development and web apps and I figured out what I needed to learn in order to join in the fray.
Reflecting on each new startup and each new step—starting my own web design and development business, building an app for predictive analytics for sales and marketing, a B2B compliance solution for licensed cannabis operators, an AI curated and generated newsletter tool for SMBs—I realized I’ve been trying to tie it all together. My mind wants to align everything into an orderly, linear path. Some premeditated and clear direction. But I can’t. It feels chaotic and reactionary, teetering on the brink of instability. Sometimes this bothers the hell out of me. That’s when I find myself on LinkedIn, scrolling the jobs.
In these moments, I need to create a bit of space; step back for a second. Temporary motion sickness is part of the experience, but it’s not a bad thing. The thing that ties everything together is the approach; a “curiosity-driven career.” There is no master plan. Instead, there’s merely a repeating pattern that goes something like this: I notice an opportunity, I get really curious about what it would take to capture that opportunity, I find the gaps in my skills and fill them in, and then I relentlessly chase the opportunity.
Two ADHD undercurrents make this possible: increased risk-taking and heightened curiosity which can lead to hyperfocus. Hyperfocus is a paradoxical phenomenon often experienced by people with ADHD, particularly ADHD-PH. Rather than struggling to maintain attention, hyperfocus is a state of intense concentration brought on by a spike in dopamine when engaging in enjoyable activities. The interaction between risk-taking and curiosity and the resulting decisions I’ve made has gradually turned me into a competent generalist—best suited for the chaotic environments of startups.
Let’s talk more about these two forces.
Risk? Startups are risk incarnate. Being naturally drawn to risk, or not even registering situations as risky, can be beneficial when you are trying to build something new. There is a downside to this inclination as well, but when you manage it properly, it can be a significant advantage.
Risk causes me the most tension. A large part of me craves order and predictability—creating systems and order is a big part of my role. A slightly larger part of me enjoys the thrill and possibility of the yet to be known. It’s exhilarating to imagine that something I build could help hundreds or thousands of people solve a problem. Risk is an irresistible pull towards possibility—a gamble where the potential payoff far outweighs the security of the familiar. It’s choosing to leap into uncertainty, knowing that the landing might be more extraordinary than anything I could have planned.
So you’re ready to take a risk, great. Now what about curiosity?
Startups, building things, and creating things require several different skill sets. These skills are diverse and unconnected, so there isn’t a clear way to learn everything you need to know ahead of time. Instead, you’ll pick up the different skill sets along the way. Curiosity drives this learning. The best way to learn something completely new is to be intensely curious about it—what it is, how it works, and how it fits into the larger requirements of the new thing you are building.
This is where the heightened curiosity of people with ADHD becomes a huge advantage. Curiosity comes in two types:
Epistemic Curiosity: The desire to fill knowledge gaps, which leads to extensive research and exploration of different subjects. This helps you rove around the startup environment and gather new skills to create something innovative.
Social Curiosity: An interest in understanding others’ thoughts and feelings. This helps you constantly improve the thing you built—taking in the feedback from your users and genuinely caring about their feelings toward it.
David Epstein covers a lot of this ground in his book Range. Specific to curiosity and startups, he shows that curiosity can be a powerful force for learning, particularly in complex and unpredictable environments. Curiosity sends you on an exploration where you gather a bunch of information that can be used in several different contexts.
When you’re trying to capture a new opportunity, you’ll naturally gravitate towards some systems-thinking. This involves seeing the problem or opportunity as a part of a larger system—a bunch of interconnected components or pieces.
Holding this constellation of parts in your mind, the next task is to assess whether you understand each piece. When you don’t, curiosity fires up. How does this work? Who has done this before? Who does this well? A rabbit hole opens up. You can’t help but wander inside. You’ll enter a state of hyperfocus akin to a flow state. Subverting the ADHD norms of being highly distractible, following your curiosity can turn you into a tranced-out knowledge collector.
As Epstein writes, “The most successful people are those who explore broadly and then focus deeply.” ADHD sets this in motion perfectly.
When you are in a startup environment, you’re running this program of curiosity over and over and over. You’ll apply it to many different problems in each domain of the company.
At one of my startups, GrowFlow, I followed my curiosity across various marketing strategies and funnels, learning how to cold call and sell, onboard new customers, build an onboarding machine, and address churn by getting curious about engagement. After a while, I led “growth” for the company by staying curious about each stage across the customer journey and working closely with each department head.
Slowly, over time, I collected a broad skill set and a broad understanding of how everything works. Did I become world-class in each domain? Hell no. Was I able to see the entire playing field? Absolutely.
Taking risks, wandering with my curiosity and cementing a broad set of skills across several domains is the most important skill I can have in today’s world, in spite of the side of me that craves order, predictability and a linear path.
This is where I find myself now. I’m the holder of varied skills, well suited for the startup wilderness and ill equipped for the well-traveled roadways of established companies. Reflecting on this more closely, I’m okay with this situation.
The thread I’ve been searching for, to tie everything together, is some version of “personal mastery.” That term feels a little grandiose for my tastes, but the concept is fitting: a lifelong discipline that involves personal growth and learning. Personal mastery is one of the five disciplines in Peter Senge’s influential book The Fifth Discipline: The Art and Practice of the Learning Organization. Senge frames personal mastery as the use of questions and being inquisitive in an effort to see reality more accurately. This is the feeling I get from my uncontrollable curiosity—I need to understand the reality at play.
This is what I need in all my confrontations with my experience—the ability to see reality as accurately as possible. This is what startups need too: they need to understand the reality of their users and the problems they solve for them. The goals are one and the same.
Even knowing all of this, I can’t honestly recommend my career path. It can be confounding, risky and unstable. Plus, there is luck needed in nearly everything. Luck in timing, luck in your idea, luck in the people you meet in the startup wilderness.
I also acknowledge that this approach may not help as much when you venture outside the startup bubble. Later stage growth companies create happy nests for specialists, and that’s a great thing. It’s not lost on me that my experiences are just that: my own.
What my example points to is a possible alternative to the eight-plus year grind or the rigor required by specialization. This is hope in following your curiosity, collecting a patchwork of disparate skills and finding your own unique connections amongst the tangle of your life experience.
Things are changing quickly, or at least it feels that way. Artificial intelligence may take some of the wind out of the sails of specialization. Work will look a lot different, and so will the job listings on LinkedIn.
Change favors adaptability and curiosity. Now is the best time to be curious. Go follow your curiosity.