Thoughtful Ways to Approach a Career Transition

And how I eventually solved my years of burnout even though I was doing what I wanted

Last year, I perfected what I called “productivity procrastination”. It consisted of some actual work in the morning, lunch, the inevitable food coma, and then hours of what looked like deep thinking but was actually me lounging around in the living room checking Surfline to see if Ocean Beach was a windy mess (it always was).

Five years into running Interview Query, I'd convinced myself this was the baseline for what a dream job was running a lifestyle business. The truth was more uncomfortable. Each day I'd find increasingly creative ways to avoid my main business—reading books about niche industries, starting a SEO agency, listening to podcasts about venture capital, even launching a Vietnamese coffee supplement brand (which, ironically, hadn't helped my focus at all). I was like someone frantically trying every door in a hallway while pretending not to notice the room I was trying to escape was my own company.

What I didn't realize then was that burnout had me mistaking escape for strategy. I convinced myself the solution was starting something completely different when the real problem was my relationship with the business I already had. The psychological trap was elegant: a new venture with uncertainty promised unlimited potential while my existing company had the inconvenience of reality, with actual customers and real plateaued revenue.

But what helped me face down the real problem was stumbling upon the Double Diamond design process—a framework that forced me to separate problem-finding from solution-hunting. How it works is the first diamond has you diverge to explore all possible problems before converging on the root issue. Then the second diamond has you diverge again to explore all potential solutions before converging on the right one. This was my revelation: I'd been jumping straight to the second diamond without doing the work of the first.

When I finally admitted I was burning out, I used this framework to dig deeper. Was it that revenue wasn't growing fast enough? Was it the endless responsibility of handling everything myself? Was it FOMO watching AI startups raise millions while I bootstrapped? The Double Diamond made me sit with these questions rather than racing toward answers.

For most burnout sufferers, our instinct is to make the biggest change possible, like switching careers entirely. As a founder, my version was launching new businesses (hello, Vietnamese coffee). And I've watched non-founders make even more dramatic leaps—software engineers suddenly joining volunteering for Ayahuasca retreats, without considering the spectrum of possible changes between "do nothing" and "burn it all down."

And once you’ve identified your root problem in the first diamond, the second diamond's divergent thinking revealed something crucial: there are three main dimensions of your career you can modify, each with different levels of disruption:

• Your role: This is changing what you do day-to-day while keeping everything else constant. The software engineer who moves from frontend to backend, the product manager who becomes an engineer, or the manager who returns to being an individual contributor.

• Your company: This is changing where you work while keeping your role similar. The fintech engineer who joins a healthcare startup, the marketing manager who moves from a corporation to a nonprofit.

• Your larger professional industry: This is the most drastic change—leaving your entire professional ecosystem. The banker who becomes a teacher, the corporate executive who starts a business, or the tech worker who moves to Bali to become a digital nomad.

Funnily enough, all of these changes can be large outsized career transitions. But due to strange unnamed behavioral principle, I think many of us go for the most drastic option first, even before they consider all other options. But I would argue that changing your role or the company you work for also has an equally large impact that creates an equally strong solution alternative.

For myself, I noticed that even going from part-time COO and part-time CEO to full time CEO might not sound all that drastic (and I probably wouldn’t update my LinkedIn for it), but it could dramatically change much of my day to day job to something that I might enjoy much more. Over the years I realized I was never great at managing large amounts of people, projects, and initiatives. But I’ve loved having deep focus time to work through all of these ideas and cohesively place them together.

Similarly, a founder of one company who eventually starts a second will create a much different atmosphere. Going from a 20,000 person company to a 10 person company or working in the payments industry to working in small business payroll, you’re not just changing companies, you’re fundamentally changing your day to day, even if your role remains the same.

So what I started to do was create the matrix of creative possibilities to flow into the alternate realities that could exist. For example when I went through this exercise, I decided to run through the top three options in each.

Changing my role from CEO / COO / running Interview Query

• CEO / Thought Leader of Interview Query

• Owner / Board of Director for Interview Query

• Full time content creator for Interview Query

Changing the company I worked at

• Staying at Interview Query

• Running an SEO Agency

• Starting a new VC Funded AI Company

• Starting another bootstrapped business

Changing the thing I’m doing now

• Starting companies and running them

• Writing books and running a Substack for a living

• Becoming a value investor and picking stocks

• Becoming a monk or deciding to retire from capital endeavors

With these different option, I started to mix and match to see which combination really excited me. In some ways, they’re not all equivalent. You can't really be a value investor and then pick a company and a role, without then making pivotal decisions as working for someone else or raising money. But you can start from the role itself and compare how the opportunities might fare down the line.

For example, I compared being CEO for a new VC funded AI company or just doing it for Interview Query. What would I have to give up in each situation? What would the price that I had to pay? Or being a content creator for Interview Query or a new SEO agency? What does my day to day look like in each? What advantage did I have for starting over vs having a baseline following to build on?

Slowly as I did this exercise, I realized what resonated with myself. At the end of the day, it’s hard to really know until you commit to trying. But the initial thought exercise at least helped me knock off some immediate options I thought in a cursory glance would be a good idea.

When I started Yo Drink → I wanted to keep the role of "Founder" while switching the company to "Yo Drink / Selling D2C E-commerce” and continuing in the larger professional industry of "Entrepreneurship" and building companies. And when I think back on it, the mistake I made conflating finding a way out of my existing day-to-day role vs starting something completely different.

For a while I truly thought it would be a skater / surfer lifestyle brand too

One of the last crucial additional questions that helped me realize all of the options and select the best reality was isolating down to one question: if 90% of my day to day in this situation was still going to be a grind, a slog, and I wouldn’t continuously be seeing success in my results, would I still do it?

Realistically everyone’s career is going to be a slog most of the time. Work is called “the grind” for a reason. And part of the grind is understanding what day to day activities you’re willing to endure and build resilience on to achieve compound effects. Burnout I’m starting to realize, is somewhat inevitable. But some activities are inherently enjoyable and may last longer than others over a lifetime of working in that field.

What I ended up deciding was that I didn’t want to switch industries, nor did I really want to start a new company in another field. I really did enjoy the overall mission at IQ which is helping people land new jobs and up-skill themselves. But I was getting tired of managing my role as a whole.

It took me 9 months, but we finally hired a GM to take on the job of running Interview Query. How that goes, time will only tell. But it’s a good step to take, albeit costly, long, and overall surprisingly tough to execute on and put into motion.

Maybe this is too rudimentary, I don’t know. I would love some feedback on it. But it helped me really re-evaluate what I was doing. And ultimately I think it’s made me happier for it.

Some additional helpful articles that address this issue

• I think everyone is going to remember their own first few experiences working retail / entry level jobs in high school or college and reminisce and agree that the experience was better for them.