Writing to Yourself

What might your past and future selves tell you?

I was lucky enough to officiate our friends’ wedding this weekend. We were surrounded by great friends, strong families, and an ecosystem of relationships all around the bride and groom. Lots of love.

In the words of DUNE, “A beginning is the time for taking the most delicate care that the balances are correct. This every sister of the Bene Gesserit knows.” Weddings are always times to look back and look forward, and times to bring positivity and energy out into the open. It made me think about the beginnings of some of the projects and companies I have started, and the hopes and dreams that are floating in the air at that time. What you might say to people going through those moments.

Have you ever tried the exercise of writing a message to yourself in the past, or in the future? It gives you a perspective on yourself and your current problems, and creates a stronger thread in time between the past and future versions of yourself. And when you read it later, it creates a snapshot that connects your current self to both of those versions.

I feel like it is a good tool for creating more empathy for yourself, which is powerful. Empathy for your past self allows you to learn from and move forward from mistakes. Empathy for your future self helps you create the right path and good habits for the future. Empathy for your current self helps you give yourself a break! Who might you write to?

For example:

  • Write to yourself AT the age of 80 - what are things you want this person to know? What are things you hope to give them?

  • Write to yourself FROM the age of 80 - what are the things your 80-year-old self might say to you now?

  • Write to yourself at the age of 15 - what advice do you wish you had received from a wiser, older you?

  • Write to yourself going through a difficult time in the past - a relationship breakup, a business failure, a medical emergency, a death. What did that person need to hear?

When I speak to startup folks who are early in their journey, of course a lot of things come up from the start of Farm.One and Gengo. So this week I decided to write a letter to myself in 2009, when I had just started the company and we had just a couple of employees. We were working out of a co-working space in a concrete building next door to a place selling very affordable Chinese bento boxes, which formed the bulk of my diet that year. We were obsessed with launching something great and finding a way to market it to customers. Early on I had brought on co-founders to help me tackle the huge technical job of building a distributed work platform, and in late 2009 we were just starting to hire new folks and expand the team.

Dear Startup Founder / 2009 Rob

You are so full of energy, ideas and plans. You seem to have few doubts or second thoughts, and an unlimited passion for designing, building, making things. You share your plans with everyone who will listen, and look out for new friends everywhere. You are trying to solidify a grand plan.

You are excited to build something fun, something light, something positive. The imagery and tone of voice and the ethos of what you are building is designed to be fun. You are inspired by the folks around you who have done the same. You want to get something out there, and try for the first time to have something of your own out there in the world. You see the web as a place of opportunity, a vast new land to explore and stake your claim to. Making a webpage, making an app is incredibly fun and feels like an accomplishment. You feel like you are bursting with potential.

You are not sure of the scale of what you are building. You are sure you don’t want to work on it for a long time, because you have a hundred ideas. You think this is a short project that you can complete, and sell.

But you may be on a longer journey than you think. The code you are writing now might persist for a long time, and form the core of a much larger system. The people you are working with now might form a bigger part of your life than you expect. The energy that you are putting in right now might need to last for a long time. The decisions you make, or avoid making, might stay, and bounce around for years to come. The small choices you make every day might turn into culture.

If you accept this might be a long journey, how might you remember what is important outside of this project? While no one will blame you for missing the occasional birthday or event with your family, nieces and nephews, how will you find a balance over the long term? You might be driven to put every ounce of creativity into this new shiny thing. How might you make sure you have something left for yourself?

The passion and fun that you bring to making things will be infectious. Less obvious cultural things might be infectious too. What culture are you creating? You know how to respect people because you’ve always been brought up that way — but might you be taking that culture of respect for granted, as you grow? You’ve always easily understood technology and handled complex design problems — are you taking it for granted that everyone can do that too? How might you find ways to appreciate these talents in yourself, so you can appreciate them in other people? How might you find ways to make clear the important things that you have always had, and you have never felt the need to talk about?

You are delighted when others are interested in what you are doing. You feel grateful for their support and camaraderie. You feel like you know each other, and exactly what each other wants, because it is laid out as a startup roadmap by tech journalists and startup founders who have gone before. You know there are some small areas of tension, some slightly different ways of doing things, but you are all busy and focused on what is right in front of you. How might you keep awareness of these things, and keep this vessel in good repair as it travels? How might you tighten loose knots, repair small nicks and scratches as you go along?

As you launch, and attract customers and workers, you are making small decisions that only affect a few dozen people. Decisions about pricing and pay rates and how to qualify people. These small things can of course be adjusted, but how might you talk about the reasons behind the decisions? How might you give people who are coming on board a voice, and a way for you to know what adjustments you need to make over time? What might happen when these decisions are multiplied by a thousand, or a million? What might happen when you have multiple management layers, and things are done and said that go against principles you never realized you had to communicate? How do you recognize the intangibles?

You are bringing on new team members, just a couple of folks at a time. You bring the culture of your previous companies, consciously and unconsciously — you work hard, you have drinks after work, you gel with comrades who are cynical about bullshit, you are suspicious of folks overly-obsessed with money and commerce. It is incredibly fun and feels rebellious and cool. How do you keep the good parts of this, and identify what might not serve you in the long term? How do you bring in new voices?

May you have space to enjoy the present, and space to nurture the future. May you know that the problems of today are real, but many will not exist in a year’s time, and others that you were not aware of will have turned out to be more important. May you keep that incredible energy and infectious enthusiasm, and keep building positivity into what you do. May you create the future, and see that as a joy and a responsibility.


2024 Rob

I coach CEOs, founders and executives on how to reach their full potential, become great leaders, and scale strong, impactful companies. It works.

If you like reading about leadership, work and culture, but are also OK with forays into subjects like creativity, worldview, psychedelics, farming, startups + reality, then I recommend you subscribe to this newsletter. It’s free.

Join the conversation

or to participate.