The Glorious Walks

Below is one of my favorite passages from Roald Dahl’s “Boy” about his father:

He harboured a curious theory about how to develop a sense of beauty in the minds of his children. Every time my mother became pregnant, he would wait until the last three months of her pregnancy and then he would announce to her that ‘the glorious walks’ must begin. These glorious walks consisted of him taking her to places of great beauty in the countryside and walking with her for about an hour each day so that she could absorb the splendour of the surroundings.

His theory was that if the eye of a pregnant woman was constantly observing the beauty of nature, this beauty would somehow become transmitted to the mind of the unborn baby within her womb and that baby would grow up to be a lover of beautiful things.

Call me an optimist, but I’ve always believed that these ‘glorious walks’ were a perfect parallel to undergoing any kind of experience in this world (good or bad) as they provide the necessary empathy and inspiration for bringing your ideas to life.

Great designers often started their journeys by viewing and recreating as many existing designs as possible. A common thread amongst honest designers states that “All creative work builds on what came before. Nothing is completely original.”

One of the first things I was taught as a young budding product manager was to take apps or products that I admired and deconstruct them: breaking down each business model, user flow, visual design, and piece of the technology stack.

Understanding how these great products were built from the ground up gave me even more context and reference material to draw upon when it came time to build my own products.

In venture capital, I spend most of my days observing the beauty of new companies by speaking with 8-15 startup founders per week.

Increasing my reps of meeting with each of these companies is imperative towards building my mental repertoire towards understanding what makes great teams and companies tick.

This mode of thinking has provided a specific mindset that allows me to never regret or be intimidated by any kind of human experience. And that makes life so much more enjoyable.

Formalize Your Mentor Relationships

When I was much younger, I never quite understood the advice friends gave me around formally asking people whom they respected to become their mentors.

In my mind, life wasn’t supposed to feel so transactional. I built relationships with people over time and I never felt a need to directly ask someone to be my mentor.

Asking someone to be a mentor felt like the awkward dating phase in high school where you’ve both liked each other for a long time and you’re pressured into popping the “will you be my boyfriend / girlfriend” question.

Recently, I’ve gone back to square one to question my own beliefs and I’ve come to realize what a big loss it was to never formalize these mentor relationships.

Pop the Big Question

A few months ago, I met someone in my product community whom I immediately hit if off with online, so we decided to grab some coffee given he had recently moved with his family to San Francisco.

After chatting for an hour, I came to the realization that I had a great deal of respect for him in everything he had accomplished personally and professionally.

And so, for the first time ever, when the meeting ended, I verbally asked him to be my mentor. After a week of careful thought, he agreed to my request and we kicked things off.

Prepare for the Meeting

The first thing we did was establish a regular cadence of meetings. I initially felt bad about taking too much of his time, so I threw out the option of quarterly meetings. He immediately pushed back by suggesting monthly recurring meetings and we could scale back if necessary.

I came to the first mentor meeting prepared with an agenda in my notebook. There were a couple thematic areas of my life that I couldn’t prioritize and I wanted some advice on how to proceed.

We spent the hour talking through each of these “themes,” and he asked me to rate each on a scale of 1-10 (1 = not interested in pursuing this theme at all). Based on my responses, he was able to provide some objective 3rd party opinions on how to proceed.

After helping me prioritize my areas of focus, he put me on the spot and asked me to think about my one core life goal.

His objective there was to force me to distill various goals into one overarching goal that would act as an umbrella and north star.

(side note: funnily enough, this is a common exercise I do with seed stage founders that I work with. I’ll often keep digging with questions until we get to the one core KPI they want to focus on and we’ll figure out how to maximize that KPI)

We talked about a few other topics but I wanted to give you a sense of the value that I immediately derived from that first formal mentor meeting.

Document the Learnings

After that first meeting, I immediately created a Google Doc and wrote a recap of everything we had discussed, separating my notes into:

  • Raw Notes Transcript: Data dump of everything I could remember
  • Discussion Summary: Key bullet points summarizing the conversation
  • Action Items
  • Possible Topics for the Next Meeting

Writing this document is important because it reinforces the learnings in your mind and serves as a point of reference for future meetings to show that you’re actually making progress.

To recap, I no longer believe that it’s enough to have an unspoken mentor-mentee relationship where you both meet whenever convenient and chat about whatever comes to mind.

If you want to take your mentor relationship to the next level and show visible progress, formalize your mentor relationships by doing the following:

  1. Mutually agree to a formal mentor-mentee relationship (pop the question)
  2. Establish a regular cadence of meetings (try starting with a monthly cadence)
  3. Come prepared for every meeting with an agenda or topics you’d like to discuss
  4. Document learnings in writing after every mentor meeting
  5. Act on these learnings (show your mentor that you can walk the walk)