I Spent Two Years Redesigning My Lifestyle, Then This Happened

In the Rockies, photo Martin Edic

No, it’s not all bad

Tim Ferris gets a lot of credit for the term ‘lifestyle design’, though I can’t verify that it originated with him. Nevertheless, he relentlessly promoted the concept with his books, podcasts, and blogging until it became a thing. I like to think of it as lifestyle redesign since at my age I can look back and see at least five times in my own life when I changed pretty much everything, including over the past two years.

It’s really a form of reincarnation that you do while you are still alive, killing off things that no longer work and becoming a new person, while retaining your collective knowledge. Two years ago I was a software marketing executive working in the big open office of a young company. All the perks and I was not really happy with it.

This was my third software management job and while it was a great company with a great enterprise product and a pair of young, brilliant founders, I was bored. One of the things that comes up often in Tim’s books is how much of work time is just busyness, filling up those eight hours. It reached the point with me where it just felt like watching me waste a chunk of my time here on earth. So, I quit.

I got a contract job doing marketing for four hours a day, which funded my planning time. But then my ‘boss’ there decided I needed to be onsite, sitting at a desk during those four hours each day. And I was right back where I started.

This was when my sense of urgency about change accelerated. But what was the goal? That had been the real issue. I’d come to see these well paying jobs as just a means of having money in the bank and paying my bills. I’d put myself on hold.

I bought an Amtrak ticket that allowed me eight stops over 30 days

A lot of people may not know that Amtrak sells tickets that cover a time period and allow you to get off the train a number of times, then book your next leg with this special ticket. I love trains and always wanted to take one across the country. But I wanted this ability to choose where I stopped and started, while keeping costs predictable. This ticket accomplished that.

So, with little planning I quit my contract, packed a bag, and walked to the train station. My only plan was to use the long hours on the train to rethink the path of my life. This is not a story about that trip. I’ve written about it here. But that monthlong trip was a year ago and I succeeded in initiating change, in spite of the dreaded curse of 2020.

Three dimensional visualization

I got pretty far out of my comfort zone on the train trip. It had a layering of darkness that I had not anticipated and that was a kind of test for my ability to adapt. When you do these kinds of things, even in your sixties, you really recharge your engines and revamp your point of view.

This gave me some clarity about what my optimal lifestyle would be. The idea was simple: Find a way to make a living without being tied to anyone else’s agenda. On those trains, in the November dimming daylight, I had a lot of time to think this through.

It became an exercise in three dimensional visualization. I needed to see myself in a place where I could accomplish my goals. Fortunately I had a few advantages to help with this:

  • No family obligations
  • A skill set
  • Very low overhead
  • No accountability to others

I’ll touch on how I got to this circumstance over the past year and what changed (because in 2020 things change wildly).

I’m solo, and that makes things a lot easier

Being single without kids is, for once, an advantage when initiating change. For all the talk of minimalism, it is really a luxury that few families can focus on. But for me it has been a guiding idea, to work to lower my responsibilities to others.

It probably sounds selfish but I really don’t owe anything to anyone. On the negative side, I am on my own in this life- no kids to help me through old age. But I have siblings and very close friends who I consider family. And they are onboard with these changes.

Writing is the most portable skill set

I don’t travel through life with a lot of requirements. Being a writer for hire means I need very few tools, in my case an iPad, a connection, and coffee. That’s about as lightweight a toolbox there is. I rarely even talk to any of my clients and I think they like it that way.

One of the secrets of successful freelancing is to not require managing by your clients. If you can deliver the work they have specified, without a lot of back and forth, they will happily send you more and pay your bills promptly. You’re saving them time and you are helping them look good. I can’t emphasize this enough: don’t be high maintenance. Deliver early, give them more than they asked for (or expect!), and edit your work mercilessly.

As obvious as it sounds, it took me years to get this down. But in my redesign, it showed me how to minimalize the amount of interaction required as a freelancer, meaning I make more per hour of actual work and have more time to enjoy the mobile lifestyle I envisioned.

No debt, three monthly bills, spending money on experience, not stuff

This is the number one liberation strategy. Not having a big monthly bill for life. I no longer own houses. I pay rent in a building where I can lock the door and go away for weeks or months at a time and feel pretty secure about my stuff. And I really don’t need or want any more stuff.

The exception here is tools. If a tool will help me save time or accomplish a task, it is an investment. In the past year, aside from monthly bills, food, and travel costs, I have purchased very few luxuries. And my luxuries are often the simplest things like my new bread knife, which I use every day when I’m home.

But there is a luxury I allow myself. It is the luxury of experience and conversation. To sit at a bar and talk to a stranger. To try different foods. To absorb art. To walk in strange neighborhoods and get out of your comfort zone. To learn a new skill from someone who knows their stuff. I’ll spend time and money for those things.


I’ve already mentioned that I’m not accountable to many people. But I think about this a little differently. For me, there is power in being invisible. I can lock my door, walk to the train station and leave and no one will be concerned. My clients could care less as long as I deliver. My family are all pretty independent. I’m pretty sociable online so they know I’ll be in touch.

So, a year later, I have redesigned my lifestyle. The reality is that I already had all of these things but I was not leveraging them. Getting away and traveling 3500 miles on a train gave me perspective to see that. But there was a snag…

Along came COVID-19

The universe is a trickster. I set my life up to travel and just when I was getting ready for my next long trip, a pandemic set in. Lockdown for at least a year. I can be a nomad, resource-wise but I cannot justify any long distance travel. It is just reality.

But my redesign was also intended to reinforce my flexibility and openness to change, good and bad. 2020, with all its nightmarish aspects, has been a good year for me. A lot of that is luck. I haven’t lost anyone to the virus. I’ve been exposed and quarantined but no symptoms and a negative test. Being mentally set up for remote work in a remote work world has been a marketing advantage.

This piece is probably the most self-centered thing I’ve written here. But there is a reason why I’m writing about this. Redesigning your lifestyle is doable and essential once in a while. As Covid has shown us, life can be turned upside down in a heartbeat. Addressing change proactively makes us looser and less stressed when things get challenging.

My redesign is sticking. When things open up again I will be ready. And then I’m out of here! My message? You can do this.

Former software marketer. Former musician. Writer, nine non-fiction books, two novels, Buddhist, train lover. Amateur cook, lover of life most of the time!

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