How to practice deliberately in knowledge work and manage a small organisation

Executive overview

Deliberate practice transforms skill in sports and music, but translating it to knowledge work is hard: there are no coaches, no drills, no direct feedback. The answer is to identify the skill that actually matters, build a project around it, and protect the time to execute it.

The best substitute for a coach is a publicly committed project that forces you to stretch — combined with carved-out, inviolable practice time.

Deliberate practice in knowledge work

1. Identifying the right skill is not obvious — knowledge work roles are amorphous and people rarely know what actually drives career advancement.
2. Interview people ahead of you in your field. Ask for their story, not their advice — people give better data when recounting specific career steps than when put on the spot.
3. Ask the differential question: what were you doing differently from peers who didn't get promoted at that same moment?
4. Once the skill is identified, design a project that cannot be completed without improving that skill specifically.
5. Make the project public — commit to your boss, a team, or a repo. External stakes simulate the coach's feedback loop.
6. Assign fixed, protected time to work on the project. Treat it like a dentist appointment: non-negotiable.
7. Done consistently over three to four months, this approach can produce a significant, career-relevant improvement.

Managing a small organisation without support staff

• Chronic overload stems from too many open loops competing for planning bandwidth — not just workload volume.
• Consolidate communication: replace ad hoc messages, drop-ins, and async back-and-forth with scheduled office hours and a booking link for one-on-ones.
• Clarity beats accessibility — people respond better to a known process ("Thursday office hours") than to unpredictable availability.
• Automate recurring small tasks so they become background routines rather than open loops the brain has to track.
• Limit simultaneous large projects to a number you can actually sustain; keep a queue and pull sequentially.
• Reserve one full day per week for deep, reflective work — sermon prep, strategy, or whatever requires sustained thinking. It refreshes judgment and models the behaviour you want from others.

Easy vs. effective in software tools

• Easy software reduces friction on individual actions; effective software aligns with how the brain works to maximise output quality.
• Easy is overrated in a world of chronic overload — the instinct to churn quickly through small tasks crowds out the slow, focused work that produces real value.
• Tools with a steep learning curve (Vim, Matlab, K edit) can extract more from a skilled user than polished GUIs that hold your hand.
• The preference for easy software is a symptom of overload: when the only metric of progress is throughput, friction feels like the enemy.
• Slow productivity reframes this — what matters is the value and quality of what you produce, not how fast individual actions execute.

Four ideas from the military worth keeping

1. Have a creed. Elite units codify their values so members can fall back on them when conditions are hard — a personal creed does the same.
2. Serving others is everything. Combat veterans consistently report that what mattered was the people in their unit, not accolades or status. This maps to something deep in human wiring.
3. Embrace the suck. SEAL training builds comfort with extreme discomfort. The civilian version: when hard things happen, acknowledge it and ask "what's next?" rather than falling apart.
4. Discipline is freedom. Arbitrary daily disciplines — made beds, shined boots — build the neural foundation for efficacy and self-control. Discipline enables options rather than restricting them.

On stock investing as a side hustle skill

• If your stock-picking skill is good enough to teach, it should be generating enough returns to make the teaching unnecessary.
• Consistently beating the market is extraordinarily hard; even highly compensated professionals with full-time access to information cannot do it reliably.
• If the teaching feels draining, stop. Focus on the primary skill. Invest surplus capital in index funds.