Lifestyle Experiments I’ve Learned From
last updated 4/19/24
My closest friends and family know I’m the last person in the world who enjoys drawing attention to himself.
I don’t even like celebrating my own birthday. Not because getting older bothers me, I just don’t like being fussed over.
Sharing my lifestyle experiments from the last 24 years with you is actually a little uncomfortable for me. I’m not sharing them to show off or to even encourage you to follow in my footsteps.
You are you and I am me.
I want to share my lifestyle experiments to show you what’s possible.
Most of us make assumptions or have limiting beliefs about our options in life. I’m spent my career challenging the status quo.
I never accepted the options put before me. I pursued alternatives that made sense to me for how I wanted to work and live regardless of how much money, time or status I had.
I know you can do the same. The most effective method for learning about yourself and your potential is by conducting lifestyle experiments in my humble opinion.
Action is a better teacher than listening to the monkey chatter in your mind alone.
Some of my experiments are small changes to my daily habits. Others are major life events. Some are personal and others are professional.
Some I conducted on behalf of someone else’s benefit.
All the experiments I conducted take less conventional approaches to common problems and desires we all face in life. I’m sharing them in no particular order.
If you have any questions about any of the experiments below, please contact me.
lived out of a bag for two years
After my divorce in 2019, I decided to hit the road and embrace my inner minimalist by living out of a bag!
I sold my condo in Boston and put everything in storage.
Uncharacteristically, I also had zero plans about how and where I was going to travel!
I left in June 2019 and spent the summer hitting a few conferences in the Northwest and visited one of my best “Internet” friends Mike Vardy at his home in Victoria, BC.
Later that summer, a member of one of our Accelerators invited me to join her and her family in the Amazon jungle! Her husband was originally from Marajó. It was the trip of a lifetime!
As part of this experience, I also wanted to live life with family and friends. In between trips, I would live with my parents in Florida or other friends for up to a month.
I have also met loads of amazing people through my work and life on the Internet, so I had the opportunity to visit them all over the world, including friends in Melbourne, Sydney and Noosa, Australia.
Just as the pandemic was breaking out in March 2020, I was doing yoga daily in Ubud in Bali. I left there and spent the first seven weeks of the pandemic living with friends and their young children in Cleveland, OH.
I decided to put down roots again in June 2021 when I bought 10 acres of land to build a tiny house in Florida, MA. I soon discovered building a tiny home is much more expensive than I realized, so I bought a duplex with my sister in North Adams, MA!
I’m itching to start traveling again in 2025!
What I learned: Discovering what it’s like to 100% live how you want and to be guided by your feelings.
I have a tendency to plan, but found it liberating to not know where I was headed next on my journey. I had so many varied experiences I couldn’t have possibly planned, but because I was so open, opportunities found me.
I also felt validated about my minimalist tendencies. Life for me is really all about the accumulation of experiences and not possessions.
Ran my business from Spain for four months in 2010
I wanted to be able to work from anywhere, so I tested out my desire by working abroad in Seville, Spain.
This was well before the whole “digital nomad” thing.
At the time I was running my online sales training business LocalBroadcastSales. I never told any of my clients and learned a ton of new ways to run my business more efficiently.
Everything went smoothly and working abroad exposed me to more efficient ways to run my business I don’t think I would have ever discovered if I stayed home.
What I learned: I made a huge discovery. How to live two days in one!
Seville is six hours ahead of where I was based at the time in Boston. My “American workday” lasted from 4pm to 9pm in Seville, so I had the entire day to enjoy living in Spain and could even go out for tapas after I finished my work!
Helped get a friend out of $20,000 in credit card debt in two years on a $50,000 a year salary
The trick to getting out of a mountain of credit card debt on a limited salary is to design your lifestyle around your commitment to eradicating your debt. Period.
I worked with my friend to make some dramatic changes to her lifestyle. She ended up living with her aunt to wipe out her largest expense for six months, her rent. She made deep cuts to her entertainment budget and put every penny she saved toward paying down her debt.
However, it’s important not to completely cut out expenses that give you pleasure. You need some treats to help you stick to your financial diet. My friend loved going out to eat. She ate our less, but didn’t cut that expense out altogether because it was one of her top enjoyments.
Once you create the habits for getting out of debt, you’ll never look at your money the same way again. It’s your first step toward financial freedom. Once my friend paid off her credit card debt, she started saving for a down payment on a house.
What I learned: You can get out of debt on your current salary.
It’s true, you might have to make some uncomfortable choices, but those changes are temporary. All it takes to make yourself debt-free is to commit to designing your life around eliminating your debt.
Eradicated paper from my life
My life has been fairly paper-free for the last two decades. Paper is one of the key sources of clutter in the home. I don’t like clutter!
Clutter is draining because it requires you to have to make a bunch of decisions you don’t want to think about.
I still use toilet paper, but will be installing a bidet this year (2024) to remove that last bit of paper use from my life!
What I learned: When I first started eradicating paper from my life in 2005, I discovered getting rid of paper was more than eliminating clutter.
It showed me I had much more control over my life than I realized. It provided me with a template for purging other areas of my life that made me feel drained or inauthentic.
Stopped consuming all news media for three weeks
I was a history major and I’m a lifelong news junkie. Up until this lifestyle experiment, giving up news media for even a day was a huge deal for me. Sometimes you learn the most about yourself from the toughest challenges.
Funny story, as a result of this experiment I missed the coverage of one of the biggest news events of my life: the capture of Osama bin Laden! Even stranger, it took 48 hours before I even heard about it!
A friend finally told me about it. I lifted my news media ban for 12 hours and gorged on the coverage. It made me feel angry, sad and anxious.
It immediately made me realize the purpose of my experiment: how things out of your control can unnecessarily distract you from living your life on your terms.
What I learned: Most information from media is designed to entertain, rather than inform.
If you want to be a truly informed citizen you need to be intentional about the information you consume and where it comes from.
I still struggle with my news addiction and regularly take week-long breaks from it. It never ceases to amaze me how much more positive I feel when I live without consuming “the news”!
been off social media since 2021
I admit it, I was never a fan of Facebook. That was the first to go. I started to abandon it in 2015. I finally deactivated my account in 2019 along with my Instagram account. I had no regrets and still don’t.
As part of my decision to pause Life Skills That Matter in 2021, I stopped using Twitter and LinkedIn for the most part.
I still use YouTube because I consider it a publishing platform. Fortunately, I never got sucked into TikTok.
I admit, I loved Twitter. I was on it since 2009. I met loads of incredible people who became friends. Its design was simple, elegant and useful.
It was a useful source of information until slowly the volume of noise from those seeking attention on the platform grew too much for me to handle. I deleted my Twitter account at the end of 2022.
I love keeping up with my family and friends, but prefer meaningful in-person visits and phone calls. I enjoy using video chat for business.
They are more personal, human and engaging (needs for my personality type). Yes, it might take more time, but it forces me to slow my life down to focus on the people who are most important to me.
What I learned: I’m not missing out.
I stayed on Facebook as long as I did because I thought I was going to “miss out” on something. I haven’t missed much because all my friends keep me up to date with what’s happening on Facebook anyway!
My colleagues keep me in touch about the latest trends. They act as a filter by sharing stuff they know I’m curious about or is aligned with my values. They prevent me from wasting time sorting through all the clutter on social media.
Performed a cleanse
I decided to try a cleanse in 2011 because I was curious about how my food consumption affected my energy levels throughout the day. (You feel how you eat.)
There are lots of different types of cleanses out there, but I chose the one by Dr. Alejandro Junger after reading his book, Clean. I was drawn to it because of its focus on detoxing the body. I also liked the fact that I was NOT going to have to survive on fluids alone like many other cleanses!
It was more of an elimination diet to see how different foods affect you. It took three weeks. I’ve never had to worry about my weight, but the cleanse made me realize, how much I ate out of boredom!
I was also able to identify foods that drain my energy (grains, sugar) and those that boost my energy (fruits and veggies). As much as I would like to be 100% vegetarian I realized I needed a little meat in my diet to feel satiated.
I know it’s common sense, but doing it versus reading about it made me “feel” the change, so I was more likely to commit to altering my diet.
What I learned: I want to eat to feel energized, not comforted.
Comfort foods feel good in the short term, but drain you over the long term.
Gave up watching television for four months
I stopped watching television for an entire summer. Sure it was a little easier to give up because summer activities offer plenty of distractions.
However, I was surprised how many times I instinctively reached for the remote during the first week. I never considered myself a heavy TV watcher (around 10 hours a week), but I was indeed hooked on the boob tube.
When I bought my current house in 2022, I decided not to own a television. I do still catch shows by watching them on my laptop, but I’m less inclined to watch on a smaller screen.
What I learned: Television was artificially keeping me up beyond my natural bedtime.
After a few weeks, I noticed I was getting up an hour earlier. I didn’t realize that I was starting to go to bed earlier because my old friend the TV wasn’t keeping me up!
I never ran more than a mile in my life until I completed a half-marathon after six months of training
I actually lost a bet. (It was the first time the Patriots lost to the Giants in Super Bowl XLII). I always enjoyed biking, swimming and weightlifting, but not running.
Once I make a commitment to someone, I always follow through. The friend I lost the bet to was an assistant athletic director at the time.
She helped me design a training regimen to get me ready for the race. A couple of other friends lost the best with me, so we provided each other with weekly accountability check-ins about our progress.
I finished in three hours flat. I never want to run one again, but now enjoy running a few miles from time to time!
What I learned: This is such a great example of challenging my limiting beliefs and my assumptions about my physical capacity.
I now use this experience as a frame of reference to challenge myself in other areas of my life.
Gave up alcohol for five months
I drank a lot in college. Too much. After college, I worked in New York City for nine years and went out three or four times a week. Drinking was part of the culture.
It was a regular habit in my life. By my late 20s, I wanted to experience life without alcohol. It wasn’t that hard to give up.
I discovered it’s harder for me to stop after three drinks than not to drink anything at all.
What I learned: This significant habit change in my life showed me how many of my social relationships were based on drinking.
It began a process of looking at how fulfilling my relationships actually were for me.
It also saved me a ton of money (about $400 a month, yikes!)
As of 2024, I no longer drink alcohol at all.
Conducted a social purge of all negative people in my life
In 2011, I was rethinking the direction of my life and realized I had a lot of negative influences in it.
I’m generally a fairly positive, optimistic and happy person, but I felt my energy being drained when I hung out with certain people.
I made a list of all the people I felt were too negative or I didn’t feel a meaningful connection with them any longer. I felt liberated. I felt energized.
I made room in my life for new people who were more in alignment with the direction I was taking my life. Within four months of this social purge, I started dating an amazing woman. I often wonder if I would have if I didn’t do this social purge.
What I learned: Breaking up is hard to do and is especially hard with friends.
Sometimes the reason that brought you together has faded because you have both grown in different directions.
You both are still great people, but you no longer fulfill each other in the way you once did. Sometimes those old relationships are holding you back from who you want to become.
Paid off my $5,000 credit card debt within a year of getting laid off
I love reading. The first book I read after being laid off in 2000 was Rich Dad, Poor Dad. (I strongly recommend you read this book.)
The first action I took after reading the book was committing to eliminating my credit card debt. Even while on unemployment I started hacking away at my debt.
The focus of my lifestyle was to become debt-free. Once I paid off my credit card, I maintained my rigorous habits to start building up my savings to eventually become financially independent.
What I learned: Spend below your means and always pay yourself first before any of your other bills.
Saved enough money not to have to work for the next decade based on my current lifestyle
Once I paid off my credit cards, I focused on building up my F**K YOU savings.
I believe a very simple method of defining your wealth is calculating the number of months or years you don’t have to make money by living exactly as you are right now.
First, you need to understand the cost of your lifestyle. How much do you spend to live the way you do?
Once you understand the cost of your lifestyle, you’ll want to assess all your spending to make sure it’s in alignment with how you really want to live your life.
Nothing will get you more motivated to cut your expenses than putting a spotlight on unproductive spending!
Second, you’ll want to save your first month’s worth of expenses and then another until you have at least a year’s worth of savings to cover all your expenses.
What I learned: I can’t express how empowering it is to build that kind of self-funding!
It gives you the ability to work on your terms like almost nothing else can.
Got rid of all my possessions I held onto out of guilt
I consider myself a minimalist, but even I was surprised to discover how much stuff I hung onto out of guilt!
After reading The Life-Changing Magic of Tidying Up I was finally permitted to let go of all the stuff I held onto out of guilt.
I held onto gifts people gave me because I felt like I had to and stuff my parents gave me when they moved out of our family home.
I never wanted any of it! I let it all go and it made me feel amazing!
What I learned: I realized everything has a purpose, not just living creatures, but inanimate objects too.
When you hold onto items out of guilt you are denying them their purpose.
Worse, you are weighing yourself down with guilt.
We hold onto stuff out of guilt because we want to honor the person who gave it to us.
A better way to honor them is by enabling the gifts they gave you to live out their purpose once again by giving them to someone else who will appreciate them in a way you never will.
(I still haven’t had the courage to tell my dad I sold his childhood train set he gave me! Honestly, the person who bought it was thrilled and I knew they would appreciate it more than I ever would.)
Worked from home for 24 years
I was a “reluctant entrepreneur” for a very long time. I was never taught about self-employment as an option. At the very least when someone did talk to me about it, I was told it was “too risky”.
Now I am happily and proudly unemployable. I am far more productive working from home than working in an office or even working remotely for a corporation.
I believe the pandemic was a big eye-opener for many office workers, who realized how unproductive offices can be!
I have always had enough income to sustain myself through all the ups and downs of the last 24 years.
I truly believe more and more people will become “reluctant entrepreneurs” like me, but I hope I can show you how to become “proudly unemployable” instead.
What I learned: Once you liberate yourself from the shackles of traditional employment, you have the opportunity to decide how you want to work and on your terms for the first time in your life!
Until you do it, it’s hard to imagine!
Designed a business that paid me a passive income of $250,000 a year
Before I even heard the term “passive income” I had created an online sales training business that did just that.
I spent a couple of years building an online archive of 600+ training videos.
The last three years I owned that business it paid me an average of $250,000 a year for roughly 20-hours of work per week!
Never did I think I could create such a lucrative part-time job! (Of course, I put in a TON of work the first couple of years to get it going.)
I ended up selling the online portion of the business in 2012.
What I learned: I now have a completely different view of my income.
Never again will I trade my minutes for dollars (even when I consult!)
I always want to create value and income by building systems that can run on their own and that I own.
Wrote two books in two years
I’ll admit these were not best sellers, but they did pay my bills!
I had never written a book before, but was paid $20,000 to write my first book!
It was a history of the New York State Broadcasters Association. I turned 100 interviews into 200 pages.
I was asked to write a second book on “how to get a job in media” while I was writing my first book.
It was an intense experience, but it taught me a lot about how to generate quality content very quickly. A skill that is still incredibly useful to me today.
What I learned: I could take on a daunting task I had never done before by making a plan first.
Making a plan makes huge projects seem more achievable. They help you understand how you can break them down into smaller, more achievable takes to tackle on a daily basis.
I know this might not sound like a “lifestyle experiment” per se, but when you want to take on a huge professional challenge like writing two books in two years, your lifestyle gets completely reorganized around that big goal whether you like it or not!
Saved $1700 by renegotiating all my monthly bills
You’d be surprised how much money you can save every year just by renegotiating your monthly bills once a year!
Typically, I save between $200 and $500 a year for a couple of hours of work each January.
I once saved $1700 by doing extra research on competing services for all of my monthly bills.
I negotiated with each of my service providers and told them it was cheaper to keep me as a customer than the cost of acquiring a new customer.
What I learned: Everything is negotiable. Everything.
Attend conferences for free
I’m a huge advocate for attending conferences. They are a great way to meet lots of like-minded people and acquire specialized knowledge very quickly.
As much as I like attending conferences, I don’t like paying for them. They can be very, very expensive.
I generally attend them for free by offering to speak or volunteer at the conference. I have also scored free tickets by covering the event as a “journalist”.
What I learned: It never hurts to ask for what you really want or to come up with an alternative value of exchange.
I ended up getting an apartment in Seville, Spain for ten weeks for free in exchange for consulting the management company that owned the apartment about video marketing.
Didn’t own a car the first 10 years of my adult life (except for one year)
I know cars are a necessity in most parts of the country, but they are a huge financial drain.
I was fortunate enough to live in New York City and Boston most of my adult life where you can live without a car. I did own a car for one year when I needed to commute to a job just outside of New York City.
Today, there are so many hourly car rental services, ride-sharing and Uber/Lyft that getting by without a car is becoming more and more possible.
The cost of your annual usage of these transportation alternatives is often much cheaper than paying car insurance for a year.
What I learned: Just because everyone else accepts things as they are doesn’t mean you have to.
Having a car is a “must-have” for living your life in America, but it doesn’t have to be. If you want to do something unconventional in life or your work, there’s always a way. You just have to be curious about finding it!
Got all expense-paid trip to 1998 Winter Olympics and got paid on top of it
This was the highlight of my career as an “employee”. I negotiated a temporary leave of absence from my job at CBS News to work for CBS Sports at the 1998 Winter Olympics in Nagano, Japan.
Everything was paid for, even my meals. I was paid a daily salary plus a “per diem” to cover any extra expenses I had. I ended up investing most of it. I was also able to get tickets to any event for free!
I never thought my boss would let me go, but I worked up the courage to ask her anyway. To my surprise, she said, “Yes”.
What I learned: I learned to never make assumptions and to just ask.
How many amazing opportunities do you miss out on because you were afraid to just ask?
Retrained my superiors to lighten my workload to create more time for the work I wanted to do
When I landed my second job at CBS News I was barely hanging onto the lowest rung of the corporate ladder.
Most of my responsibilities were very administrative, but I desperately wanted to learn how to produce television, instead of running around doing errands.
I quickly looked for opportunities to eliminate, delegate or automate my duties, so I had more time to help produce.
People would ask me to send their faxes (this was in 1997 folks), so I taught them how to send their own. I got endless questions about how to use Microsoft Word, so I had a computer trainer come in to teach the staff the basics. When producers asked me to do administrative work for them, I told them I would be happy to do it, but wanted the opportunity to help them produce their stories.
What I learned: Never settle for doing the job you were hired to do, learn the skills for the job you want. Managing doesn’t always come from the top down, it can also come from the bottom up.
I quit my job the day I was offered a promotion for my dream job that only paid $10/hour.
When you are starting a new career path, you can’t focus on the money. You need to show your passion for the work and your ability to do it.
Early on in my career, I was tempted to take a job with a more senior title and more money, but it was going to take me away from my goal of working in television news.
I ended up landing a job at CBS News that was actually a demotion and paid much, much less. Within a year I got a promotion and made even more money than if I accepted the promotion I was offered at my previous job.
What I learned: Focus on what makes you feel fulfilled and the money will follow.
I paid half the price for my MBA degree compared to my peers
The average cost of an MBA when I attended business school from 2002 to 2004 was around $100,000. I paid only $50,000 including the loans I took out!
I thought it was strange that business school students never used their business mindset to negotiate the cost of their MBA.
I managed to reduce my reliance on debt by securing a number of graduate assistantships, as well as working full-time during my second year of business school. Those two years were indeed challenging, but not having a lifetime of student loan debt was totally worth it.
What I learned: Don’t accept debt, even student loans (if you can). Countless students will be in debt for the rest of their lives.
When you have debt, it prevents you from focusing all your money, time and energy on how you want to work and live on your terms.
My Experiments Continue
I’m continuing to conduct lifestyle experiments. I stopped eating sugar in December 2015. I started working outside the house at a co-working space in January 2016.
I’m also happy to try out any lifestyle experiment you propose. I’d also love to here the experiments you’ve conducted as well! Send me your suggestions!
I encourage you to try your own experiments. Especially experiments that challenge your mindset, assumptions and fears.
I truly believe the only way to explore your potential is to test your limits through lifestyle experiments.
As you can see from mine they don’t always have to be dramatic to have a powerful effect on the direction of your life!
