Last year, I realized it was time to switch things up.
In 2010, my co-founder Nigel and I started Steamclock. The vision was to build products for clients, and use those profits to fund our own product development. Which worked! Mostly. We’ve built a client business that’s been growing and profitable for a decade straight, which has funded a lot of our own product exploration.
As we grew, though, a flaw in our plan became clear: trying to build your own products within a client services company puts both businesses at a disadvantage. Specifically, a focus disadvantage.
There are fundamental differences between building a product for a client and building a product startup. They justify different mentalities, approaches, and habits. When you have other revenue coming in, you can get away with hobby products – such as building a polished, well-loved app that gets a million downloads, yet loses money. For example.
These exploits may feel partially successful because they’re fun and educational and popular, but they distract from doing what’s best for the product or services business. While hobbies can be rewarding and informative, by definition they can’t support a talented team, iterating and improving towards something truly great.
Me personally, I like to build with a talented team, iterating and improving towards something great. That’s how we do our client work, and that’s what I want to do for product. But trying to do both in a combined team makes it hard to do either well.
So, last year, we started the process of splitting our client services and product development work into separate businesses.
From one perspective, it’s a simple change: despite our many product experiments, Steamclock is fundamentally a client services business. Given that, this change is less about splitting out a product business, and more about founding a new one.
From another perspective, it’s a complex change: I’ve been focused on our client services business for over a decade. Despite a lot of progress in giving our teams ownership and independence, I’ve still been a bottleneck for some key processes like hiring, marketing, and strategic planning. To focus in on product I knew I needed to push to the next level of delegation and handoff – but after 12 years I found myself a bit burnt out.
After some angst and coaching, I devised a plan:
- Take 3 months to systematically delegate, teach, coach, and document
- Take a sabbatical for the following 3 months, to recharge and plan
- Return and see what we’d learned
You know – an experiment. While I knew it was needed, I expected this process to be unpleasant and difficult. I was worried I’d come back to a bunch of firefighting and un-delegating.
I was happily wrong.
As a leader, you do two kinds of work:
- Work that’s clearly visible to your team. This is the easiest to hand off.
- Work where your team has no context for how and why you do it, or even that you do it at all. These are harder to hand off.
A big benefit to teams with a habit of transparency is that there isn’t a lot of hidden work. I’d been doing a few invisible tasks – “when we do strategic planning, this is how I prep it,” or “every quarter I run this analysis on the P&L” – but for 80% of my job, the parts of my work that needed delegation were familiar and legible to the team.
Once we had a map for me being away, a key question remained: how often should I check in? We considered a weekly or monthly checkin or review, but that would diminish the value of the experiment. Instead, we devised a very short list of emergencies I might be pulled in for – e.g. a surprise cashflow problem or the departure of a key leader. Then, we worked to set the team up with the context, docs, and explicit authority to handle everything else.
While I expected this prep work to be a grind, it was actually… fun? We have an excellent team, and the time-boxed nature of the mission felt very purposeful. I iteratively handed off my tasks, spent less and less time working in the business and more time writing docs and coaching (which I enjoy), and after 3 months of prep the team was ready to rock.
Since I am me, I knew that – without some structure – my sabbatical would quickly devolve into Allen unofficially working. I also knew that, after 12 years of full-time work, I had more side-projects I wanted to do than could conceivably be done in 3 months. I know going on a 3-month break is a huge privilege, so I didn’t want to fork it up.
To give myself some guardrails, I chose a theme for each of the 3 months:
- Month 1: Do nothing
- Month 2: Try new things
- Month 3: Prepare to return better than I left
I was not great at doing nothing. I did a lot of forest-walk thinking, reading AI papers, and completing projects around the house. While I didn’t do nothing, I successfully stayed out of my work email and Slack – and got no emergency pages from the team. Month 1 was a success.
The “Trying new things” month was glorious. I tried new instruments, technologies, fitness routines, restaurants, books, habits, movies, priorities, games, and mindsets. Not just things I’d been meaning to try, but stuff outside my comfort zone. It was joyous. Since that month, I’ve kept up the new mindset and it’s been wonderful.
I also got a lot out of the preparation month. I started going to new meetups, reading books about products and startups, and getting clear on my mission. I love product work, so I was happy to be digging into exploring and talking to potential customers, before my sabbatical even ended.
While I feared returning to a list of fires, everything pretty much… worked. In my absence, our team delivered good work, kept clients happy, and retained everybody. The preparation paid off. In contrast to the bad old days when I was the only person with enough context to make big decisions and keep things moving, in recent years we’ve developed excellent project management, operations, and Directors of Engineering and Client Services that support and execute for our clients. It’s pretty great.
Of course, there were some gaps in my absence. But having proven out what I was actually needed for – as opposed to what I was doing out of momentum – it’s been a lot easier to work through filling them with further experimentation. It’s a big level-up to go from “I worry that blog posts won’t move forward without me around” to “How do we get blog posts moving again, now that I’m not running them?”
Meanwhile, I’ve gotten my wish: I’ve been focusing more and more on product work. I’ve pursued product research questions like “How could team communication get far better?” and “How do effective leaders manage their time and attention?” Recently, I’ve led prototyping and customer validation on a tool that helps product teams work with LLMs. I’ve been learning more than I have in years, and am excited to ramp further on product work in 2024.
The lesson, at least for me, is that even when a big change seems risky, there’s a path to doing it well. In retrospect, that may seem obvious. Over the years I’d already reinvented my job repeatedly – from founder, to manager, to leader of managers – but this felt like the biggest and most daunting change yet. Still, the ingredients have always been the same: a team, a plan, and some experimentation.
And now, for more of that.