“This isn’t big enough.”

A few words that put a pit in my stomach for months. I was sitting across from a VC, delivering my first-ever startup pitch. I had been flush with adrenaline when she agreed to hear my idea, spending the days leading up to the meeting organizing and reorganizing my research. Writing and rewriting my talking points. But two minutes in, she closed her notebook and succinctly delivered the KO. Months of work was torpedoed simply because I was thinking too small. I had found something that I knew real humans valued, but it didn’t seem to matter. I left the office in a daze — my founding dream rested on securing enough funding to hire engineers who could build the product. Was it over?

In retrospect, I probably should have seen that sweeping disappointment coming. As a product leader, I had spent years authoring and managing with career ladders that implicitly gave my teams the exact same feedback. The wording varies, but there are essentially two universal truths in product careers:

• You advance by thinking bigger. Product Managers only get promoted by shipping products with more and more impact.
• The more you advance, the less you practice the craft. As you get promoted, you  stop building products and start building teams.

Taken together, they paint a very binary view of the world. I either want to lead a large product org for a unicorn, or I don’t want to advance in tech. I’m either ambitious, or I’m not.

This was my brain’s ambient soundtrack in the following years. I had always identified as ambitious, but I was struggling to find blueprints that fit my values. I was demoralized when I looked at the lives of unicorn founders and my product exec bosses. I saw almost none of the types of work that made me happy, and a lot of the work that dragged on my psyche. When I scanned jobs at early stage companies (the lottery tickets of the software world), all I saw were HR code words for “probably won’t see your family much”. I explored “senior individual contributor” jobs as a way to stay closer to the craft, but they felt a bit like the Island of Misfit Toys. A temporary staging ground for people who don’t fit a company’s orthodox ambition. I had thought founding a company would be my path to designing an ideal job, but that door slammed shut with the VC’s notebook.

I realized I was surrounded by colleagues and friends feeling the same tension — we want to enjoy our craft and connect to the people we build for, but we grind away at huge, abstract market opportunities that feel less and less human. We want to go one way, but the incentives and career ladders of large tech are walling off the path. It’s alienating a growing population of tech workers — how do you grow in an environment where your aspirations aren’t valued? My brain churned — what did this mean for my goals, my identity?

Then I heard “soft ambition”.^[1]

Ambition is about taking up space with your dreams and choices, hopefully to make the world better than how you found it. You can do that in any context that matters to you.”^[2]

The words turned me into Truman Burbank, punching through an artificial sky.^[3] All of a sudden I was in an exponentially bigger sandbox, with the freedom to set the context for my own ambition. I love building products to solve people’s problems, and I aspire to be great at that. But I also want to feel energized when I’m not working. With finite time, I don’t want to waste hours working at something that will diminish my enjoyment of the other parts of life. I finally had the tools to realize that wanting those two things wasn’t a lack of ambition, it was optimization.

Emboldened, I began searching for new environments. I spent a year experimenting with different types of freelance work, trying to find the right combination of craft and freedom. In a poetic twist of fate, the answers were hidden in the research from my torpedoed business idea. I had interviewed a small army of professional chefs, mining for product ideas. They were all looking for career paths outside the ruthless world of restaurants. One chef was working 6-day weeks for $50k a year and no benefits. And this was the executive chef of a well-funded, reputable (albeit small) restaurant. Chefs loved cooking professionally, but were turned off by the relentless grind of pursuing restaurant success — the “viable” career path. Sound familiar? But fast forward a few years, and now we’re seeing those same chefs successfully running a variety of non-restaurant food businesses: specialty food producers, pop-up dinner series, virtual cooking schools, and more.

What changed? Chefs didn’t all of a sudden realize that restaurant life is hard. A quick peruse of Kitchen Confidential shows that it’s been a grind for at least the past 20-30 years, if not longer. Look a little closer, though, and you see that the emergence of creator platforms like Patreon and Substack happened around the same time. Virtually overnight, chefs could channel their soft ambition in a new direction. It was a tiny crack in the wall of opportunity, and chefs turned it into a flood.

I realized that a similar crack was staring me in the face. An idea had jarred loose the first time I coded with AI, when it dawned on me that I could build products solo. Stumbling upon soft ambition gave it form. These tools meant I didn’t need to hire engineers, which means I didn’t need funding. I had the power to explore non-venture tech businesses, to pursue my craft on my own terms. In theory, I could think “small”.

Armed with my new blueprint, I went back to the whiteboard. I looked at my wife and I’s goals and found our “enough” number — the number that would provide for our family and enable our ideal lifestyle. I did the math. It was entirely possible to hit that number with small tech. And selling a software product meant I didn’t have to sell my hours. I would be able to shape my life around my family. It would be hard, but the energizing hard — not the soul-crushing kind.

With the freedom to think small, I stopped feeling cornered by my career and started seeing opportunity everywhere. Without the pressure to think at venture scale, I had a much deeper pool of solvable problems to explore. I’ve started talking to specialty small business owners and “1000 True Fan” content creators. Researching Reddit communities and cohort programs. I’m hunting for everyday small problems that can be solved with well-made, focused software products. I’ve taken to calling it Craft Tech^[4], and if AI will be its engine then soft ambition will undoubtedly be the fuel. It’s by no means a given, but the sheer volume of simple needs that can be solved with software gives me optimism that I can create a career that fits my values. One where I can focus on my craft, build useful things, and spend time with my family.