Designing the Life You Want

This is a really scary essay to pull together, but there’s a lot swirling around in my head and I wanted to write it down. I needed a focusing lens, and this is the medium.

If you had the ability to take a year and retool yourself, with the benefit of 20 years of adult life experience, what would you do? This is my personal exercise for the next year.

I’ve actually been thinking about this day for a long time. I wanted to make sure I fully understood my rationale for, as well as my expected outcomes from, this decision to take a year off. I wanted to be clear in defining my North star principle, as well as the supporting philosophies.

They key issue is: I no longer wish to live the life designed by the person I was 20 years ago. Therefore, I have made the decision to focus this sabbatical on “designing the life I want to live.”

We grow and change in life. Who you are at 41 is unlikely to be who you were at 21. I was reminded of this fact a few weeks ago when my Facebook feed was flooded with pictures, messages, and updates from the 20 year reunion for the University of Pennsylvania class of 1996. Sadly, I couldn’t be there. It looked like an amazing time of reconnecting among old friends.

I did, however, spend most of that weekend reflecting on this impending decision. I also reflected on the person I am today versus who I was when I graduated. Specifically, I focused on:

  • What kind of person, husband, and father I am, and want to be
  • How I choose to spend my time
  • The type of people I allow to be close to me
  • From what I derive fulfillment in my work
  • My purpose; my why

Unsurprisingly, the young man I was when I left Wharton with my MBA (one year after undergrad) is in many ways different than the man I am today. Reflecting during that reunion weekend, the passage of time was front and center in my mind, and I kept asking myself, “what are you willing to do about it?”

Men are often imprisoned by the chains of their own forging.
- James Michener, “Texas”

As the time drew closer to finalize this decision, the thing I have worried about the most was what other people would think. It generated a lot of fear. For good or bad, my whole life has been an advert for type A behavior. As such, throughout this process I was constantly hearing the voice in my head saying that I must always be achieving more and more. That if I get off that path or do anything different than that, I am a failure, that I couldn’t hack it, that I wasn’t good enough, and that I didn’t have “it.”

That kind of self-talk is extremely hard to overcome. It weighs so very heavy on the soul.

Further compounding this negative self-talk is the amount of impact one’s job, position, or even product on which they work can have on an individual’s perception of self-worth. The internal conflict between everything that you have been told by parents, educators, and employers about the right thing to do, the right place to study, or the right place to work or even what type of job to have, and your own internal dialogue about designing the life you want to live can be quite straining.

And yet, here we find ourselves.

My wife once asked me if I had any big regrets in life. One was that I never served in the military. The other was that I allowed myself to rush through school, always with an eye on over achieving, becoming a ba-billionaire, and being the CEO of some such company or other. I went from kindergarten to MBA from ages 4 to 22. I was handed my MBA on a Sunday afternoon, and I was at new employee orientation for my job at Microsoft the next morning.

I used to tell myself that I rushed through school so that I could be self-sufficient. Having grown up in a single parent home of an alcoholic parent, it wasn’t the most nurturing of environments. I never worried about food or shelter, but I’ve been on my own income statement and balance sheet since April 1, 1994, thanks to a national minority engineering scholarship I earned from Microsoft, and running a tutoring business in college.

Even though I recognized the lies I told myself, I never took time to solve the real problem, which is that I never really figured out who I was.

So that’s what this year is really about. It’s a year long sabbatical to take the time to design the life I want, as opposed to praying at the altar of Restricted Stock Units, sacrificing to get one more promotion or more salary/bonus, or chasing a sense of purpose and meaning from working on “the next big thing” as opposed to “the thing that makes me happy.”

I have been UNBELIEVABLY FORTUNATE in my career. I cannot underscore that enough. I have worked in amazing companies, for amazing leaders (Bill Gates, George Soros, Jeff Bezos, Eric Roza), with amazing people, building amazing products (Microsoft Office, the first server blade, Windows Phone, Kindle), for amazing customers (the dev community is still my fav). Those are all, and will remain, very fulfilling things. I owe a giant debt of gratitude to all of the people who have enabled and or participated in that journey.

I am also incredibly fortunate to have met the woman I married. She and I couldn’t come from more different backgrounds. Seeing the world through her eyes helped remove me from the echo chamber that was responsible for so many decisions in my life.

About eight years ago, we started being very purposeful about our lives, and our lifestyle. Specifically, we focused on monthly budgeting, getting out of debt, and not growing our lifestyle to match our wages. Hat tip to Dave Ramsey. This sabbatical decision was many years in the planning. As a result, while I am paying for this time on our dime, the bill and the interest rate is so much lower than it otherwise could have been.

I have spent a good number of years in my adult life pursuing different forms of competition. In the last decade, I have been extremely focused on endurance racing. Mostly half and full distance Ironman triathlons, but also long distance mountain bike racing, and the odd marathon. The most important lesson I have learned since taking up this avocation is the same lesson, it turns out, that my wife and I took away from the planning and budgeting our lives: there are no hacks or shortcuts.

Progress is measured in the hours and hours of toiling away when no one is looking.

There is no hack to qualify for Ironman 70.3 World Championships. There is no hack to become financially independent. There is no hack to finding self-fulfilled happiness.

Progress is often undetectable because the timescale at which it operates is much longer than the short attention spans of those seeking hacks.

Some people are blessed with talent. Others develop skills to compensate for their lack of talent. Skill development takes time. And commitment. And understanding why you are doing it. And support. If you want to build new skills, or improve on the ones you have, it takes time and effort, with a dusting of luck thrown in for good measure.

There are no hacks. There are decisions, effort, outcomes, and time scales.

My decision is to design the life I want to live. The effort will be full commitment. The outcome is unknown. The time scale allotted at this point is 1 year to solve this problem.

It’s not in me to go forward without a very specific goal(s) or plan. Operating in such a free form mode is hard for me. Stressful even. Going against my ingrained habits, my current plan is intentionally high level and vague, to be flushed out over the coming weeks. In order of immediacy, my plan is to:

  1. Decompress. 29 years (high school through MBA through all of my employment to today) of super hard charging lifestyle imbalance takes a toll.
  2. Quests. My inner D&D nerd is coming out. Some quests will be small (i.e. dust off my SQL skills, write some python code, etc) and some will be large (be part of the construction crew for a house). Some make sense today (spend 10 hours of work each week helping my wife with her real estate business), and others make no sense in that they have no immediate applicability to my current situation but are of high interest to me (i.e. learn a third language). All of these quests are meant to make me a better, more well rounded person. I will be focusing my writing over the next year on capturing those adventures.
  3. Design the life I want. I do not know, at this time, what success looks like, other than “a happier me.” I do know that I love technology, and it’s ability to improve lives. I love building products. I love working with customers, and helping solve their problems. I love public speaking, which is something I miss doing. I really enjoy spending time outside, on bikes, running, swimming, skiing, travelling, playing with my kids, you name it. Put simply, going on adventures. I’ve been told by many people in the last couple of years that they are inspired by some of my adventures and racing. In a few cases, some have told me they started running or biking because of this inspiration. Seeing some of the transformations in old friends and family who are pursuing healthy lifestyle choices, and encouraging them to overcome their fears and help them plan for their successes, has been extremely rewarding. I’d love to do more of that. Somewhere in the intersection of those things is the life I want. It will need to provide a reasonable living wage, with reduced stress, more time for my family, and enable me to be around people who share my passions and values. I do not expect this to be easy to solve. I am open to any ideas if you have any that you want to share.

This isn’t retirement. It’s designing the life I want to live.

This isn’t jumping off the train. It’s getting off at a station to check my bearing, and then get on the right train.

This isn’t abandoning my career. It’s about cementing my current skill set, while mixing and laying the mortar for the skills I want to build.

This isn’t privilege. It’s years of hard work and planning coming to fruition.

This is, however, a privilege. This is a gift. This is an opportunity. This is a beginning.

This is one of the bigger risks I have ever taken in my life. I have no idea how it will turn out, but there is no time like the present.

Why now? It’s pretty simple really. I left Amazon to join a small software company, that was going public, as part of the executive team. Within a few months of joining, the company was bought by Oracle. Oracle kept buying companies to add onto the newly formed division. Instead of being the top product guy in a growing company, I was one of many senior product guys in a now very large division of an enormous company. It wasn’t what I signed up for, and 18 months post-transaction was long enough. With that as a logical stopping point, now seemed like the time to take the opportunity to avoid having a huge regret on my deathbed of that thing I didn’t do.

Time is the only currency that is constantly draining from your account. I didn’t want to lose any more of it by just showing up, going through the motions, and clipping a coupon. It’s time to step off the path and create a new one.

Do not go where the path may lead, go instead where there is no path and leave a trail.
-Ralph Waldo Emerson
It’s amazing how much thinking you can get done when you run outside. I’ve spent countless hours on this trail.

There are paths ahead, and paths that go backward. There is the great unknown of the path not yet forged. Which one you choose is up to you. The decision may not be clear, and clouds may lay on the horizon. Never forget your job. Be a better person today than you were yesterday. Be productive. Create things. Care for people. Learn. Read. Emote. Adventure. The rest will sort itself out.

This is day 1.

Originally published at Many Niches.