Check out Phase 2, my podcast about quitting my job to find more fulfillment in my work life. You can find it on Spotify or Apple Podcasts. Below is a transcript of episode 4. If you haven’t heard episode 1 you may want to check that out first.
Well, I’m back in Seattle after traveling for 2 1/2 months. We spent 6 weeks in Minnesota with my wife’s family and 4 weeks on the road where we had memorable adventures exploring the national parks and wildness of the American west with our two young kids. If you haven’t heard about our trip, I encourage you to checkout the first 3 episodes of the podcast.
The good thing about being on the road is that I didn’t have to think about what’s next. As we got closer to home, I started to feel the weight of having to figure out a plan. I could almost hear the stopwatch ticking, and each tick sounds like a cash register ringing of the money slowly disappearing from savings.
In my first week home I felt pretty aimless.
Everyone else in the house was fully focused on getting started with school. We made the decision over the summer to home school our kids with all the Covid uncertainty. My wife took the lead on this and has formed a pod with our good friends and neighbors who have 3 kids around the same age as ours. So she was fully occupied while I was left with no remaining excuses – I need to figure out whats next.
One thing my coach Ravi had asked me when we started to work together was to think about what a great life looks like. I’ve thought about this over the past few months and I think it boils down to this for me:
- First, deep connections to my family and friends. I’m grateful to say I’ve got this.
- Second, a healthy mind and body. So far so good there.
- Third, work that I enjoy and that is personally meaningful to me.
Oh, and I need to make enough money to support our current lifestyle. And save for retirement.
I know what you’re thinking: no shit sherlock, everybody wants those things. Easy to say, not so easy to do.
This reminds me of that famous law of software development: A project can be High Quality, Low Cost or Done Fast. You get to choose 2 out of 3. What will it take to achieve everything? Will I need to break some laws?
Finding meaning in my past
I’ve been reflecting back on examples of times when I felt fully alive or there was meaning in what I was doing.
Creating this podcast has been a great recent example. I felt deeply engaged in the process of crafting them which felt equal parts creative and cathartic. The response I got from the first episode was quite overwhelming. Hundreds of people commented on the initial facebook post describing it as “courageous” and “admirable”. I don’t think there’s anything courageous about it – I was just describing how I felt and it’s interesting that people find that to be so unusual.
Many people private messaged me about it including complete strangers. Several people asked to meet so they could learn more about my rationale, share their own situation and ask for advice. I felt ill equipped to give them advice since I haven’t figured anything out yet.
However, for the first time in probably a year, I jumped out of bed in the morning to check the listener numbers, excited to work on the next episode. Thanks to all of you who continue to bug me to publish new episodes – they’re coming, people.
Looking farther back, there are a few other examples of times in my life where I felt truly alive:
One time was when I volunteered at a school in a Nepali village teaching English and Computer Science classes. Over the course of two weeks, we helped our students create a documentary about life in Nepal to help raise awareness for the volunteer program. It was such a fulfilling experience. We got to be creative devising interesting lesson plans while filming the documentary. We felt good about helping people who had so little but that were so grateful for our efforts. Checkout Volunteer’s Initiative Nepal for more info.
Another time was leading a product design workshop at Microsoft with low income middle school kids in the Seattle area. That was fulfilling because I got to use my expertise to support a group of motivated and enthusiastic kids. Checkout the DigiGirlz workshop.
Another time was my first year working at Upwork which was a bay area startup connecting US clients to freelancers around the world. There I got to observe the kind of transformation that is possible when people in developing countries getting access to opportunities they wouldn’t otherwise.
Another time was the thrill and terror of launching a brand new service at Amazon, which is kind of like watching a baby get born: its really messy, you don’t know if you’re going to make it but no matter what happens, you’re know you’re going to love it.
Finally, my friends and I used to traipse around Seattle creating music videos for birthday milestones. Those moments of goofing around with close friends while being creative together were some of the best memories of my life.
There are a few themes that emerge from these experiences: First, there’s a theme around creating a tangible output whether that’s a software product, a video or a podcast. Second, there is a theme around teaching or mentorship as a way to have a positive impact on people around me. Third, there’s a theme about working with people rather than in isolation – I know my best ideas come when I’m brainstorming with others rather than an office by myself. Finally, there’s a theme around wanting to operate within a realm where I can be an expert at what I’m doing.
So how do I find a job that has all of these elements in it?
Like it so far? Subscribe here
Friends who’ve transitioned
One thing my coach suggested I do doing this period is to seek out people who have made transitions in their own lives, or are doing what I want to do so I can learn from them.
Over the past month I’ve probably talked to more friends and colleagues from my past than I have in the last 5 years. Which is a bit of a sad statement – why did it take a life crisis to re-engage with all these people from my past?
I spoke to my friend John, who quit his job as an engineering manager at Microsoft after 10 years to become a high school physics teacher. He explained to me why he decided to leave, which was a combination of seeking a lower stress life, more family time and more connection to impact. He talked about how the impact he has on the trajectory of his student’s lives – many who are first generation immigrants. His impact has been more significant on them than any of his time in tech.
I spoke to Josh, who is a high school friend of my wife’s. He reached out to me after I posted the podcast about similar feelings he was experiencing around lack of satisfaction in his work despite financial successes. A discussion with his 10 year old daughter Isla prompted a recent career shift for him. Take a listen.
I spoke to my friend Steph, who I worked with many years ago at Microsoft. Recently, shes been taking time between jobs to figure out what’s next. She has been helping one of her college friends who owns a nail salon, figure out how to pivot her business in a post-Covid world. She told me that helping her friend in such a direct way has brought them so much closer together than they were previously. She also told me that she talks to her mom and grandma much more frequently than she did when she was working and that this extra time has also brought them closer together. If our connections with loved ones are what ultimately bring us happiness, why do so many of us have to leave our jobs to truly invest in those relationships?
What makes my friends come alive?
I’ve talked to various friends about what brings them alive. An investor friend of mine said he gets a thrill out of defending an investment proposal through hard questions from partners. Another friend talked about belting out a song that exemplifies a moment or emotion she’s feeling. My coach told me he loves being in deep conversation about the human experience. A designer friend loves doing the art she wants to do rather than the art she is paid to do. A skier friend lives for difficult and dangerous runs he’s not sure he can do.
While there were as many answers as people I talked to, the thing that jumped out the most was the theme of high performance in risky circumstances – whether on the stage, in the board room or the ski hill. There was also the theme of getting lost in the moment whether that is doing a design or conversation with a client.
Next I look at what kind of job can combine all these things I care about.
Product managers love defining requirements
Here are the requirements of the working life I’m trying to create:
- First, I need control over my time and ability to set my own schedule. Previously, working in Corporate jobs I was at the mercy of the cadence and demands of the company.
- Second, I want to work less than 6 hours a day to give me time to enjoy kids, exercise, get outdoors, etc.
- Third, I need to do something I’m naturally good at or can learn to be good at.
- Fourth, I need to find something involves helping people or solving a problem that really matters in the world
- Finally, its got to generate 20k+ / month since Seattle is a pretty expensive place to live and my wife doesn’t work oustide the house.
It seems that starting a business of some sort would be one of the only approaches that could satisfy all these insane requirements. So I started brainstorming ideas:
- First ideas is to create a community of people who are looking to make their own career transition and help them do it. This podcast has had a great reaction from my community and I am convinced there is a market need for people around my age who want are dissatisifed and looking for more in their working lives. I could turn my own journey it into tools and resources to help them in the form of courses, manuals or coaching services. This feels important in the world, would have a tangible output through podcasts and content and parts of it feel aligned with my abilities. On the other hand I’ve never done anything remotely like this in my working life.
- Second, I could start a consulting business of some sort focused on PM best practices or lessons learned over the past 10 years. I could build a community via substack, publish podcasts and videos. The downside is that there’s already a lot of content like this out there and plenty people more qualified / accomplished than me. The upside is that in the people out there who have my exact background and experience is… well… 1. I think helping others in their own career would be meaningful but no idea how big the market is for this kind of content.
- Third, I could start an ecommerce businesses of some sort. I have a few ideas for products, although, nothing that is particularly important for the world or that I feel very passionate about it.
- Fourth, I could try to start a software company. I do have a couple of ideas on problems that are personally meaningful to me. I would need to validate the problems with customers, recruit and hire a team, possibly raise money, then start the long path to finding product-market fit. While I have worked on software products my whole working life, starting something from nothing feels terrifying and exhilarating. Which makes it seem like the right place to start.
Samir Lakhani 