I recently left Replit and now on a break—grateful for a memorable year there. My break started with a wonderful trip to San Diego, relaxing in the desert with loved ones, and now back up in the bay area. One of the people I caught up with was Bob Baxley, a design executive I look up to. who recently left his executive role as well. There are two topics Bob and I bond over: making software and sports. We equated both of our breaks as the offseason before going for another championship run with another team.

Let's use the offseason of a professional athlete as a tech operator taking a break between roles and teams. If you're not into sports, no worries. In this instance, the offseason refers to the period of time when regular activities, competitions, or events are temporarily paused or reduced in intensity. In the sports world, the offseason is the time between the end of one season and the beginning of the next. During the offseason, teams and athletes typically take a break from regular competitive play.With indefinite down time, I'll share a few areas I'm focusing on to fine-tune myself and be as effective as possible for whatever is next.

Rehabilitation and physical conditioning

Many high performing athletes ache and fight through physical damage throughout the season—playing through a litany of injuries until they no longer can. The offseason is when the much-needed surgeries and rehabilitation occurs. Tech operators endure a mental intensity like this through the grind. Our craft isn’t as physically demanding as a NBA basketball player on the court. However, our bodies are impacted by poor posture, terrible diets, and other aspects of inactivity that hurt our bodies. I recently went a traditional Thai massage, where my body got cracked back into place of how it was supposed to be positioned.

When we need to perform with our mind, we need physical stimulation to recover. They say if you work with your mind, rest with your hands. This is why it’s important to touch grass, make things with your hands, and do the polar opposite of nudging pixels and writing code.

What I’ll do:

• Work analog with pen, paper, and physical books to reduce screen time

• Exercise, diet, and physical therapy to heal the body from sitting like a shrimp

• Go on walking conversations to catch up with people

Skill development and practice

The offseason is a time to sharpen the blade. Performing at a high level day-to-do doesn't give you adequate time to develop new skills or improve skill gaps. Early in his career, LeBron James was a subpar three point shooter. Knowing that his body would give way later in his career, he invested in improving his three point shooting.

When I left One Medical, I wanted to improve my communication skills. I started teaching UX at General Assembly, which allowed a one-to-many setting where I needed to clearly communicate concepts for understanding. I started this newsletter in order to work on my consistency and writing. Skill development and deliberate practice is the critical area to focus because it requires large blocks of time to go deep.

What I’ll do:

• Reduce reading trends and hype about AI and read deeper research

• Design and build interfaces in various code frameworks

• Use Play and Xcode to get acquainted with mobile patterns

Strategy planning

Strategy planning for the coach of a team might be assessing team needs, reviewing game film, exploring new offensive systems, and re-thinking how you approach strategy in general—a time to be strategic about strategy.

A mentor once suggested committing a big block of time to reflect on the previous role while it's fresh on your mind. This provides insights and learnings for what you bring next—what you want to double down on or need improvement. I write an Impact Doc and Work Journal as ways to track progress.

What I’ll do:

• Re-read and refactor notes in Obsidian to see if there are sparks of ideas

• Write email updates to career advisors

• Review and update the Career Management Doc

Recruiting

If you're a manager, you should always be recruiting, even if you don't have a job. Many new managers are too short-sighted about recruiting and focus only on open headcount they need to fill. Instead, build a talent network of incredible product people, engineers, and designers that you'll recruit for the rest of your life. It's common for me to hire designers at a company where I've been recruiting them from 1-2 companies ago.

The offseason is my time to strengthen those relationships with previous team members and individuals I haven't head the pleasure of meeting yet. Start thinking about talent who will become free agents (AKA they're looking for a new role) and start recruiting.

What I’ll do:

• Update my Design Talent CMS and review who I should be talking to

• Scout designers by proactively looking at their portfolios and study their work

• Connect with my go-to external recruiters to understand how they're seeing the lay of the land

Looking forward to the next run

It's a place of privilege to take an offseason in the first place. For that, I'm grateful. I'm looking forward to my career offseason to sharpen the blade, heal, reflect, and reconnect. I'll be well-rested and ready for the next season to make another run at it.