Side projects as cross-training

How side projects can make you better at your day job

One of the hidden benefits of side projects is they provide cross-training for skills which make you better at your core job.

At Amazon, there’s a big writing culture. Any proposal, strategy, or new project starts with writing documents in prose. Documents get a lot of scrutiny and can sometimes take a long time to write (the first 6-page strategy document I wrote at amazon took me over 60 hours and 10+ revisions).

As my day job has become more focused on strategy and operations, I’ve needed to write more documents.

Last week, my boss expressed concern about how many documents I was writing. Knowing how long it takes people to write documents, he was concerned about how many hours I must be working in order to produce that volume of Amazon writing.

That conversation clarified one of the hidden benefits of my writing this newsletter: it’s helped me constantly exercise my writing muscles and made me an efficient writer. For 40 straight Sundays, I’ve had to polish and ship a piece of writing that I’m proud of. While some people at Amazon often deal with writing block and other forms of inertia when writing documents, I’ve developed to muscles to open up my laptop, write for 3 hours and produce a strong draft that I’m willing to ship. I’ve also complimented the reps I’m getting with Amazon-style writing with a different type of writing. Writing different things in different styles has improved my pliability in writing. At Amazon, the range of documents I’ve needed to write is starting to vary more widely. Recently, some the documents I’ve needed to write are different from any documents I’ve previously written. My Amazon writing experience alone does not give me the requisite experience or skills to write my next document. But the cross-training I’ve done through writing this newsletter has built writing muscles that help me adapt quickly to the needs of the document I need to write and create a strong first draft quickly. Writing this newsletter has served as cross training which has improved my performance in my core job.

Side-projects-as-cross-training can be used in two scenarios: to add variety in your “training” for skills you’re already building in your day job (like my Amazon writing + newsletter writing) and when your day job is not giving you the reps you need to develop a desired skill.

With the first scenario, Steve Nash is a great basketball analogy. He talks about how cross training with soccer made him a better point guard. It game him better footwork, better court vision, and more creative passing skills, as he had to practice these skills across different contexts. Steve Nash became one of the best point guards of all time, and is widely considered to have some of the best court vision and passing creativity the NBA has seen.

With the second scenario, a good analogy is a basketball player who wants to become a 3-point shooter, but the coach doesn’t want him to shoot 3’s and wants him to say inside. Without getting to reps shooting 3’s in practice, the player can’t build the skills needed to demonstrate to the coach that he’s a capable 3-point shooter. That player would need to find ways to practice 3-point shooting outside of the typical day-to-day (AKA side project) in order to demonstrate to the coach that he should be involved in 3-point shooting drills in practice.

Back to my own reflections, my transition into a more internally facing role has helped me build new skills, but I no longer spend time in my day job coaching founders — a skill that I love exercising and want to continue improving. If I limit my “training” to the core responsibilities of my day job, my founder-coaching skills will not only not improve, they will atrophy.

Therefore, I’ve sought side projects (within Amazon and outside) which force me to continue getting reps coaching founders. I do my fundraising workshops and courses with partners like On Deck, which helps me continue to build those muscles. Despite not getting these reps with my day job, the fact that I’m building these founder-coaching muscles do make me better at my day job. They help me deepen my founder empathy and better understand what varsity-level founder coaching looks like — two things that are important for my role.

My day job gives me plenty of reps with skills of skills I want to develop — managing, operations, hiring, strategy, writing, and more. Complimenting that with cross-training via side projects force multiplies some of that skill development (e.g. writing) while ensuring I’m getting reps with other skills that are important to me (e.g. founder coaching). My side projects not only serve as a method for diversifying my time investments, they serve as cross-training which makes me better at my core job.

When thinking about potential side projects, it’s worth considering if they can be used as cross training to make you better at your core job. If you can figure this out, then your core job and side projects will create a flywheel of skill development.