As my life progresses I find myself mentoring more and more people, generally a few a year.

Particularly so as I made a few huge decisions, for example to leave the professional workforce and become a traveller, writer, and motorcycle journalist.

There are two questions I ask every person mentor that really make them think. In many ways, these questions make people mentor themselves. This reflects how I like to work with people. I don't ever tell people what to do, I just help them think about it and make their own decisions.

Here are the two questions!

The most important question: Rank What You Value

The question:

Rank the following in order of importance to you.

  • The company you work for: E.g. Lyft, Google, the Government, yourself
  • The industry you work in: e.g. computers, mobility, motorcycles
  • What you do day to day: e.g. analysis, coding, talking to colleagues, pitching and selling to clients, travelling a lot
  • How much money you make (short- or long-term)
  • Inspiring leadership: How amazing either your boss, or the company senior management is
  • Great colleagues: How awesome, fun, noble the people around you are


Think how important each of these things is in isolation, and then compare them against each other.

Give a short description against each item in your ranking, which is more useful than the actual ranking.

It's useful to make acid tests, like for example "If you want to code, and you want to work for Google... would you rather be coding and working for another company, or not coding and working for Google?" or "If you want to work in tech and make a lot of money, would you work in tech and make $150K, or not work in tech and make $250K?"

There's no clean ranking, and everything "depends", but the descriptions are really informative to helping me understand people.

The second question: Define your 6-month and 5-year ideal vision of your life

This is a very hard question and often takes time to really answer.

The question:

Throw away every preconception of how you think you "should" lead your life, based on what you've done so far, and what your friends or people you know are doing.

Now imagine how exactly do you want to be living your life

  • In six months time?
  • In five years time?


This is a hard question to answer because it seems everything in our lives has led us up to a certain point.

This includes what we've studied, our parents, our friends, the country and society we live in, and even religion.

For example our parents might value medicine. Our religion or society might place a large emphasis on working in a job. Friends might be doing things in finance, or starting their own businesses.

Whatever we see around us tends to be what we perceive as being possible.

There are two time frames because in six months time seems really close. For example if you hate meetings and are in too many, you'll immediately think "Well I don't want to be stuck doing more of these damned meetings." You'll imagine yourself working on a startup or having fun or travelling or something.

Five years time is more ideal, but it really lets you picture a fantasy life. For example, you might think "I want to be in Africa, helping build a company that reduces plastic pollution, because that will feel really good." Or "I want to have published books and be living off the sales."

Whatever it is, it's extremely hard to make this vision and takes a lot of reflection.

Think about the things that give you great joy. For me these are things like

  • Learning languages
  • Being with the people I love
  • Writing
  • Riding motorcycles
  • Learning new sports

What are your answers?

If you want to share your answers privately I'd love to hear them. There are no wrong answers and they're likely to change over time!