The YOLO Economy Is Here To Stay: How To Live Your Best Life

Are you ready to live your best life in the YOLO Economy (You Only Live Once)? I sure as hell am! I believe the YOLO Economy is here to stay for the next 10 years. Everybody get excited!

When September 11, 2001 happened, I had just moved to San Francisco from Manhattan as a 24-year-old. The event was traumatizing, especially because I was at the top of World Trade Center North Tower hosting a Latin America conference that January.

9/11 reminded me again that life was fragile and uncertain. When I was 13, I had experienced similar trauma when a friend had died in a car accident.

By age 22, I had already decided I needed to save and invest as much money as possible to be free. A career in finance was not sustainable due to the long hours and constant stress.

The Decision To Live The YOLO Lifestyle

Then on November 26, 2008, there was a terrorist attack at the Taj Mahal Hotel and Oberoi Hotel in Mumbai, India. Just a month earlier, I had been staying at the Oberoi Hotel for an Indian Investment Conference my firm was hosting at the Taj!

When I saw the events unfold on TV, I remember asking myself, “Is death catching up to me?

I didn't want to go to India that year because I had already been with a client several years earlier. Back then, it took 24-hours to get to Mumbai from San Francisco. Further, I didn't want to be away from my girlfriend for that long. I had an engagement ring burning a hole in my pocket since the spring. I wanted to propose!

But my big boss in Hong Kong insisted I go because we were just launching our new India research and banking initiative. If I had died in Mumbai before being able to propose I would have been pissed.

When you compound 9/11 with my close call in Mumbai and the subsequent Global Financial Crisis, I really wanted to get the hell out of finance once things recovered. It felt like spending a career trying to make money and helping institutional clients make money wasn't the best use of time. So in 2012, I left.

Preparing For The YOLO Economy

I've been living the semi-YOLO lifestyle since 2012. The lifestyle entails doing exactly what I want to do when I want to do it. It is mostly because of living this lifestyle since a relatively young age that I feel rich. Yes, I gave up a crapload of money to be able to live free. However, the freedom has been worth it.

It is obvious the YOLO Economy will be here for quite a while. The daily messages of death from the doomsday media since 1Q2020 should have done something to change the way you want to live.

In my newsletters and with my posts, I've done my best to stay positive during these difficult times. But man, the mass media has a great way of beating us down IF we pay attention to it!

The YOLO Economy has the following attributes or desires:

  • More flexible work locations
  • More flexible work hours
  • A more purposeful and interesting job
  • An increased amount of wealth due to increased savings and investments
  • Less patience to deal with work and social BS
  • More desire to spend more of your money before you die
  • A permanent desire to live better with the money you have (nicer home, better travel, etc)
  • An increased occurrence of highly speculative assets rising and falling

The best time to work could really be right now given the flexibility and higher pay. Let's now discuss how you can live your best life in the YOLO Economy.

Living Your Best Life In The YOLO Economy

Here are some things I think you should do to live a better life. It is now more acceptable than ever to do these things. This acceptance is one of the key benefits of the entire world going through a pandemic together.

1) Look for a new job already.

If you are bored with your job, don't believe in the company's purpose, or don't like your colleagues, you owe it to yourself to find a new job! The economy is rebounding and companies will eventually find it extremely difficult again to find high-quality talent. As a result, more work perks will be offered. Be bold in your job hunt and in your demands!

Many publicly-listed companies have much larger hiring budgets because many companies are trading at all-time highs. Further, private companies are cashed up because the amount of funding available is at all-time highs.

If you are happy with your job and don't want to move, then by all means be more aggressive in asking for a raise and a promotion. The job market is hot and there is more flexibility for employees than ever before.

You don't have to follow my path and leave work altogether. If I was 34 years old today, I would be ecstatic at all the new opportunities that are becoming abundant in the YOLO Economy. Although, if you're thinking about retiring early, definitely go through my pre-retirement checklist so you do it right!

2) Calculate your Boot and spend it.

So much money has been made since the pandemic began. Your Boot is the amount of EXTRA money you've made thanks to the pandemic.

Take a moment to calculate your investment and net worth returns since January 1, 2020. Now take 13.4% off those gains (ex. 30% return in S&P 500 – 13.4% = 16.4%). The difference is the boot. The 13.4% comes from taking 10% from 2020 and 3.4% after a quarter in 2021 to get to a 10% return for the year.

If we assume the S&P 500 would have returned 10% a year had there been no pandemic, then any excess gain is a bonus. That bonus can and should be used guilt-free to pay for a better life.

The other portion of the boot is the amount of extra savings you have accumulated thanks to the lockdowns. Compare the difference in savings between the start of the pandemic and your normalized savings pre-pandemic. That difference should also be freely spent.

Using the boot is a great way to revenge spend. It is also a way not to let the pandemic defeat you mentally. As an optimist, you must always look at how bad things can help us keep moving forward.

In my case, I'm using the boot to get back to early retirement life again. I've always had trouble spending lots of money since I was a kid. But not any more! When economies fully open, I am spending my boot on first-class flights, the best meals, hotels, and entertainment, new sports equipment, massages, coaches, and maybe even a new car.

3) Build an online platform to make money and share your voice.

A part of the YOLO Economy means being able to do your work in more flexible locations thanks to the internet. I clearly remember the immense joy of earning $1,000 when I checked my phone at the top of Santorini, Greece in October 2011.

A UK-based advertiser wanted to advertise something on Financial Samurai and I obliged. Just 30 minutes after I put up the ad, he Paypaled me the funds. I ended up ordering another over-priced Mythos beer while overlooking the crater because I felt so rich.

The money was completely unexpected on my hike up the hill. Further, the ease at which the funds were made helped give me the courage to leave my job the next year.

The YOLO Economy
My YOLO moment in Santorini, October 2011

There is special joy in making money from your website while exploring new places. It's all about being able to do two enjoyable things at once. This way, you feel like you're not really working. The joy of making money on your own is at least 5X greater than being able to work from your laptop for another company.

Making Money On Your Own Is Addicting

First of all, it is satisfying knowing that if you didn't build your brand or your business, nothing would have happened. Second, you have more flexibility making money from your website than you do for an employer who allows you to work from anywhere.

Once I was paid the $1,000, I turned off my phone and drank more beer. Yum! If I was working for a company, I would have likely had to keep my laptop or phone connected for hours that day.

Another benefit of having your own online platform is that you can speak your truth. It feels great to share your thoughts about issues that are meaningful to you. If you grow large enough, you might even have the ability to positively affect change.

Having an online platform is key to benefitting from the YOLO Economy. If you can work remotely, it's easier to start your website because your employer can't track everything you're doing anymore.

Perfect! Just be smart and use your personal computer to setup and work on your side business to keep it on the down low. Some companies track browser history and usage on company devices.

4) Be properly invested in the YOLO Economy.

If there is really going to be a boom for years to come, you want to be properly invested in the YOLO Economy so that your net worth continues to grow.

Calculate the percentage of your net worth that is invested in risk-assets like stocks, real estate, art, collectibles, cryptocurrencies and more. If you believe in a bull market because everybody will be spending a lot more money to live a better life, then you want more exposure not less.

Here are my suggestions for how much risk exposure you should have by age:

20s: 100% of net worth exposed to risk assets

30s: 90% of your net with exposed to risk assets

40s: 80% of your net worth exposed to risk assets

50s: 70% of your net worth exposed to risk assets

60s: 60% of your net worth exposed to risk assets

At 43, I have about 85% of my net worth exposed to risk assets, maybe more if I include this website. My website helps give me more confidence to invest at this stage because it is a cash cow.

Of course, some assets are riskier than others. However, I have always had between 10% – 20% of my investable assets invested in growth stocks or highly speculative investments.

Since college, I've always been hunting for unicorns too. Books-A-Million was my first hit. VCSY was my second. Tesla was my third. Even if my unicorns blow up, I've still got 80% – 90% of my investments in less volatile assets.

If a recession eventually comes, at least we'll find solace knowing that everybody else investing in the YOLO Economy will have taken a hit as well. That's the beauty of continuing to all be in this together.

5) Find the right, leveraged YOLO job.

Step one to benefiting from the YOLO Economy is changing jobs if you aren't happy. However, to fully take advantage of the YOLO Economy, you also want the right job to gain the most amount of wealth.

In my opinion, there is no better YOLO Economy job than being a Venture Capitalist. You get to risk other people's money, get paid a handsome salary while you wait, and earn a good percentage of your client's profits if the investments hit big. If the investments all turn out to be duds, you don't have to pay your clients back. Further, there’s no need to grind and build anything! The risk/reward ratio is the best there is.

Another great job is being a hedge fund manager, although it is more stressful than being a VC. For example, despite Melvin Capital being down a whopping 49% in 1Q20201, the owner was still able to buy a $44 million mansion in Miami!

How sweet is that? Even a donkey can do better than a -49% loss. But a donkey like me still can't afford a $15 million beachfront property, let alone a $44 million mega-mansion.

You don’t want to be the reporter reporting on the YOLO Economy. Instead, you want to be the VC or hedge fund manager making bank from the YOLO Economy!

You must find a job that takes full advantage of people with money to burn, who don't care if you actually burn it! There's a reason why things like NFTs are gaining so much popularity. There is more money out there than we know.

Bonus: Run a 7-minute mile or less

Given we're all going to be more active and free, it behooves all of us to get back in fighting shape. Being able to run a 7-minute mile should do it, regardless of your weight.

The fitter we are the healthier we will feel. The healthier we feel the greater our endurance and self-esteem. If we get really fast, our anxiety about getting crushed by a coronavirus will likely go down. Therefore, our mental health will likely improve as well

Your goal should be to feel as healthy has possible in the YOLO Economy so you have desire and ability to do as much as possible. If you don't want to be able to run away from an angry bear, at least run a 7-minute mile for your children and loved ones.

Finally, there's another benefit of being in great shape. You have less of a chance of going to the hospital and dying from COVID!

Life Will Be Wonderful Again

Most of us have permanently decided we are going to live it up with the one life we've got. We will spend our Boot, do more meaningful work, and find ways to help others along the way.

My true hope is that all of us reprioritize the things that mean the most to us during the YOLO Economy. Chasing prestige and status is a low priority in the YOLO Economy. Instead, we should work on improving our health, our relationships, and our purpose.

Having enough money to do what you want will always be a necessity. Therefore, we must continue to save and invest wisely to develop that valuable passive income. However, there will come a point where we have to ask ourselves how much money do we need to truly be happy. I found my enough back in 2012 before I had children. Today, I have found my enough again with a family.

The goal is not to win a financial argument or have the most amount of adoration. The goal is to live a wonderful life! Only you can decide whether you are living one or heading towards one. At least consider taking a well-deserved sabbatical to reassess your life.

2020 derailed my YOLO lifestyle. But at least I'm wealthier and my family is safe. I'm not letting the next few years screw things up any more! Instead, I will focus on doing what I want for the rest of my life.

Recommendation Before You YOLO And Leave Your Job

If you plan to quit your job you might as well try to negotiate a severance. A severance package provided my wife and I years of financial runway after we left our jobs. As a result, we didn't feel stressed or rushed to do something new.

Check out, How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye. The book has been refined over the years and was recently updated for post-pandemic life. I literally wrote this book to help everyone who wants to YOLO to leave in a financially better position.

How To Engineer Your Layoff Ebook New Edition
Get The eBook Now button

I was able to negotiate a severance package worth six years of normal living expenses. As a result, I was able to travel to 20 countries for a year and pursue my passion of writing on Financial Samurai. The safety net was a huge catalyst for me to quit my boring job and live life only terms!

Readers, how do you plan to take advantage of the YOLO Economy? How long do you think the good times will last? How geared are your investments to the YOLO Economy? YOLO stands for You Only Live Once.

For more nuanced personal finance content, join 50,000+ others and sign up for the free Financial Samurai newsletter. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009. I help people get rich and live the lifestyles they want. 

56 thoughts on “The YOLO Economy Is Here To Stay: How To Live Your Best Life”

  1. John and Rosemary

    Enjoyed your article and thinking about yolo Dogen.

    We’d appreciate if you or your readers could riddle us this. MSN Money recently had an article on some research on countries which ranked highest in happiness (admittedly an abstraction), air quality, sanitation, biodiversity, and habitat. Some of these categories are quantifiable. Happiness isn’t. Anyway the U.S. ranked 20th. The top finishers were (drumroll): Finland, Norway, Denmark, Sweden, Switzerland, Iceland. (Noticing anything).

    So as we pack up the RV to head to warmth and light for the winter, what are we missing here. Besides the people in these “happy” countries being popsicles for the majority of their happy lives, what else??? What have they got makes their lives so happy? E.g. ethnically homogenous populations? 30 hour government mandated work weeks? Cradle-to-grave Healthcare? Better beer? Ski boots that actually fit? Better looking blonds? Hygge?…..?

    Why should small countries that are itchingly cold most of the time be so much better than here. Interested in your thoughts.

        1. John and Rosemary

          We always have the same reaction to Maui. Once we get there. We try to avoid the big hotel thing, usually renting someone’s condo near Kaanapali 3 for as long as they will part with it. Amazed we had never had huli huli sauce before we first visited.

          We don’t care much for the plane ride and the day it takes to get there. But as the saying goes, “people in hell want ice water. That don’t mean they get it.” :)

          We’re thinking maybe we could consider dropping our dollar $tore mentality, and just once bumping ourselves up to first class to see how it is?? :)

  2. For a 73 year-old, w a PhD who has always been close to, or for the past ten years, below fed poverty level, this is an eye-opener. Loved the comments, so many people interested in a quality life and doing good. I have lived the YOLO life, but that meant no family – all my time went to study and writing (almost nothing published, btw). While poor, I lived on the upper East side in Manhattan for several years, and had my own house for 25 years. Etc. HOWEVER, best is to be here now, fully present. “To see the world in a grain of sand, and heaven in a wild flower. Hold infinity in the palm of your hand, and eternity in an hour.” Thanks again for the excellent thoughts, and to all the thoughtful commenters.

    1. Completely agree Richard. It’s always best to be here now, fully present. I am happy to know that you’ve pursued your passions and have found what makes you most rich in life— your gratitude, your knowledge, and sharing that knowledge (as a writer).

      Sam I loved this post, appreciate you reminding people that life IS good and that it will continue to get better (this pandemic is not forever as nothing ever is), and most importantly how the times have changed and with that, so has our opportunities.

      I stress to my students constantly (most are teenagers) that knowledge is LITERALLY at their fingertips. It has never been this way in all of human history!

      You can read and learn how to do anything and everything. And that means you don’t have to work for someone else anymore to have a comfortable lifestyle. Nor do you need a ton to be happy (which I have found many people have realized once COVID stopped them from being able to spend, spend, buy, buy, buy). Glad you’re inspiring others and thanks for this post Sam.

  3. Hey Sam!

    Thanks for the article – lots to think about. I was wondering about your thoughts on taking a year “off” and doing freelance work? I’m going to graduate with my bachelor’s degree in computer science and around ~280k in savings next year. (This number is from getting a full ride, various AP/college credits, winning several extra scholarships/awards, co-op work terms, and a lot of side hustles.) However, getting to this number has been extremely draining and I’m feeling very burnt out – I pull 70-80 hour weeks, and even switched to polyphasic sleeping to maximize my time. While I could take a few years to grind at a FAANG immediately after college, I’m thinking of taking a year off and doing some freelance work to destress. However, I’m quite worried about how taking a year off will look on my CV, and how this will affect future savings and compound interest later on. Let me know what you think!

  4. Hello Sam – how much does one need to make – gross pay per annum to survive worry free in California? Is it 150k? or 200k? 250k? Age 40, single, male, no kids, renting, no real estate. And wanted to retire by age 60.

  5. I think there are a lot of positives and good perspectives in this article as is the case with most FS posts. Enjoy life; enoigh said.

    It’s also equally disingenuous though to not recognize that most people are living paycheck to paycheck and don’t have the opportunity or support network to live by such a lifestyle. At the end of the day YOLO is more a luxury and less a way of life.

    1. I think that is why most of us keep volunteering, donating money, and writing for free online to help others improve their finances.

      A very important thing to remember is that it’s hard to save the world if you are struggling yourself.

      So many people I know were able to help so many other people because they first got there finances and mental health right.

  6. I’ve spent the last 5 years building my business and working 12 hour days plus 3-4 hours on the weekends. Fortunately, my business grew during the pandemic by just under 50% and still growing as we come out of lockdowns.

    I have decided for me it’s time to start living a little more YOLO. Instead of putting all my money to work for me (as I end up with a very large nut after taxes and expenses yearly).

    That said, I’ll be leaving CA and relocating to Coeur D’Alene, ID. Can you say 6.92% state income tax rate (capped) vs the 13% (and likely to go up) I’m paying now? The tax savings alone will be huge and I can use to YOLO it up!

    I plan to take up fly fishing, become handy with a firearm, 4 ski resorts are within an hour away for midweek skiing when I feel like it, water skiing and golf in the summer. When I get tired of gray winter days I’ll either visit my family here in So Cal or just book an airbnb for a business trip in Miami for a couple weeks since I have clients in that area.

    But the real YOLO thing I’m looking forward to is living closer to my 6-year old son who lives in Bozeman, MT (5-hour drive). We’re going to take month-long trips to foreign countries every summer so he can see, smell, touch, taste, hear the things most kids only get to learn about in a classroom.

    I can’t say enough how much starting a home-based business has changed my life. I can work from anywhere with a laptop and a phone and still have income. Can’t imagine working for someone else ever again.

    1. Great you are taking action! Never heard of the place, but it sounds great. Maybe there is an investment opportunity :)

      The best thing is living closer to your son. Glad you started a home-based business. You might consider thinking of things you could by with your business that could also help improve your personal life as well. Talk to an accountant!

      Related: The Easiest Way To Make Money From Home

  7. This has been my life philosophy for a while now:

    “Chasing prestige and status is a low priority in the YOLO Economy. Instead, we should work on improving our health, our relationships, and our purpose.”

    Our Soul Purpose, Health, Relationships, and Finances are interconnected. People who don’t pursue their Soul Purpose will never reach their full potential – including their earnings.

    If your Health takes a turn for the worse, your Finances and Relationships are impacted.

    If you go through a tough divorce, your Health and Finances will be impacted.

    If you mismanage your finances and have to declare bankruptcy, your mental Health and Relationship with your life partner will be impacted.

    Maintaining the delicate balance between your Soul Purpose, Health, Relationships, and Finances is the key to a life well lived. This is what it means to be truly successful ;-)

  8. I love the idea. I wonder how you think of it from a dad’s perspective though. I could quit working and live the yolo lifestyle (keep my standard of living and not work) about now. But….I have 4 kids. They would have a great childhood and college paid for but in terms of the rest of their life it would be on them. I know that’s okay, and what I had to do. But, I don’t really want them to do what I had to do. Do you want to/think your kid will have the work ethic (yes probably), luck (not a choice), and opportunity that you did?
    My kids are looking pretty bright, which is probably my bias, but I wonder if they’ll be set up to do as well as I have by society. You start taxing everything at 50% or so and it becomes pretty hard to build up wealth that amounts to much cash flow.
    I’m wanting to live YOLO but more than that I want my kids to live the life they want. The more I put aside the better chance they can live a productive life doing what they want without worrying about paying the mortgage.
    Tax laws change much and I may just say that the advantage to what I can do for them just isn’t worth it anymore. But for now: another couple years of a job I’m annoyed by but don’t hate makes sense.

  9. Ms.Conviviality

    Everytime I see a dip in my equity holdings I remind myself that the market always moves up to the right.  BUT what if the U.S. market experiences what Japan’s market did and stays flat for decades?  Japan’s market crash was caused by high valuations and isn’t that the situation with many U.S. stocks?

  10. I’m definitely YOLO’ing the hell out of 2021! My net worth has gone up over 25X my annual burn in the last year alone, and my part time side hustle is throwing off an additional 4X my annual expenses that’s been going to into savings (after tax and paying all current living expenses). Time to open up the purse strings and keep this economy rolling!

  11. Yes! As always, this is the extra motivation and support I needed. My husband and I decided to buy a waterfront home (new build to be completed in late August with a beautiful community center including pool and gym) because we want to live our best life now! Everyone keeps asking us why we are moving, but isn’t it obvious? We want to enjoy the “retirement” life while we’re still young and healthy enough to enjoy it. I’m in my early 40s and my husband is in his early 50s, which I feel is the beginning of our prime years in life. We’ve been so cautious and delaying our gratification for the sacrifice of our 4 kids, but Now is the time to YOLO!! We already got our 2nd vaccine shot and can’t wait to move in to live this active dream lifestyle – boating, fishing, swimming, biking, exercising, yoga, and drinking wine on our dock, of course.

    It’s such a dream come true…there’s no stopping us now. The pandemic has taught us that life is so precious and we’re here to enjoy it and make our mark. It’s now or never.

    1. Brendan Mirque

      My goodness, that sounds like heaven! I would love to do the same, how does one go about finding places like that?

  12. Welcome to the Millennial mindset, Sam! As WSBers will say, “he’s one of us!”

    Just kidding.

    At some point, people definitely want to spend, let loose, and do liberal things like job hopping a lot more. Heck, I’m tired of being cooped up for so long. That pent up demand will be UNLEASHED like the likes of which no one has ever seen before.

    1. Love the millennial mindset! Wish I had more of it growing up in my 20s and 30s. But then again, maybe I wouldn’t have as much well today if I did. But then again, it’s never too late to try!

  13. I am investing all of my “boot”, rather than splurging on unnecessary things….

    SAAS sector. Crowdstrike, Datadog, Okta, Cloudflare….

    I would rather spend 5 boots in 10 years than spending one boot today…..

  14. I am happy to read your take on status. I enjoy your site but the one thing that bothered me before was you talking about seeking status. IIRC you couched it as helping your kids to get in school. Status seeking is anathema to living with meaning and purpose.

  15. I always have a hard time loosening up and spending money. This year, I’ll try harder.
    We plan to install a pergola over our deck so we can use it more. Unfortunately, lumber is a lot more expensive this year. I should have done this last year! A
    Also, we hope to travel more. We got our first shot and should be fully vaccinated by summer. We’ll head to Yellowstone and take another trip to the beach later. Should be a great summer.

    1. You and me both! Spending money, or more money than normal is difficult to do after a lifetime of being so frugal. But I don’t care anymore.

      And thanks for mentioning the word, pergola. Had to look it up. You so fancy!

      Can’t wait for your wife to finally retire next year!

  16. I’m at Pebble Beach this week and the YOLO perspective is real. Most everyone I’ve talked to is a Pebble first timer. After last year they all said no more putting off the bucket list.

    I eagled the 8th hole. I decided that takes the place of the 7 minute mile:)

      1. Lol! 525 up hill. Driver, 4 wood and a 90 yard sand wedge in the hole. Made my trip!! Gonna YOLO it up at dinner

    1. Eagled the 8th hole?!?! If you said you’d made a million on dodgecoin I’d call you a liar….but that’s too incredible to make up. I took a photo when I par’d a 3. Nice play.

  17. Yes to spending YOLO money, but it’s easier said than done after a lifetime of being a saver!

    Also, I will be a contrarian here and say that being a VC isn’t always rainbows and butterflies -for many, their required capital commitments take up much of their after-tax “handsome salary”, and many don’t even return the fund or enough of the fund to get to carried interest, and when they do, it’s often a very long time out. And they’re on the road all time for fund raising and board meetings. And if the investments are duds, they’ve lost their OWN money and their investors’ money, which makes it extra hard to raise a subsequent fund.

    1. Nah. Own money? I don’t know very many venture capitalist who invest a significant amount of their own money into their fund.

      By the time people find out their investments are no good, they will have collected massive sums of money from the fees for the past 10 years. People have short memories. They can just start another fun!

      At least the pandemic enabled VCs not to be on the road.

  18. Thanks for sharing. I read the NYT article and have been a reader of your blog for a while. My struggle is whether to quit a lucrative career as a software executive. It’s not fulfilling, but I have the golden handcuffs and am also influenced by the status/comparing myself to others. I also don’t think it’s realistic for me to become a Venture Capitalist in my early 40s, so what now? Many of us are searching for more meaning, but it’s very hard to find (career) purpose in the world as it’s currently constructed.

    1. I had the golden handcuffs as well, with three years worth of deferred stock and cash compensation, and a 5-year private investment I was forced to make during the Global Financial Crisis. My solution? I negotiated a severance and got to keep all of my deferred compensation. I left in 2012 and it kept paying out each year until 2017 as if I was still working there.

      The severance was my biggest catalyst to make a move.

      1. How many folks are successfully negotiating a severance in 2021 and in what industries? The only people I have known to successfully negotiate a severance that exceeded the very strict internal guidance regarding severance terms are those with HR issues with written documentation of something like overt discrimination.

        Companies are very savvy these days and spent a lot of legal hours refining documents to protect the company from a massive severance payout.

      2. I’m curious how many folks are still negotiating a severance in 2021 and if so in what industries? The only folks I have known who have received a severance past company policy are those with clearly documented HR issues like discrimination.

        Indeed, due to the payout of severance many companies have invested significantly in a legal team that constantly refines terms to protect the company such as in the case of an exorbitant severance. Any at will employment is an employer’s ability to dismiss an employee for any reason.

        1. Many more than you think. These negotiations are always on the down low, because that is what is required when he signed the documents.

          So many good performers I’ve been able to negotiate a severance. The thing is, a lot of people just don’t believe in themselves to be able to negotiate. It’s because they don’t understand the other side of the equation.

          Here are some posts:

          People are free to quit and retire early and leave lots of money on the table. It is actually a manager’s preference. But I don’t recommend it.

          1. Alex Hamilton

            Thanks Sam, good to read these again. I’m due for a promotion and if I leave the company, they’re screwed for 6 months minimum similar to the story about your wife. However, I have found manager / company pride sometimes supersedes revenue decisions when an employee makes an ultimatum of promotion or gonezo.

            In my experience, corporate decisions are rarely rational. Good case examples though and hopefully I can make some moves this year.

  19. It’s funny, two things struck me here. 1. The boot/revenge spending, and 2. the 7 minute mile.

    1. I decided that since I couldn’t take my wife to Italy this year because of COVID, I could recreate it. So I made her a Italian day and ordered all kinds of Italian food throughout the day, and gifted her a brand new Vespa. Figured, if she couldn’t go there, she could at least live like she was. BTW I’ll get to ride the Vespa as well – so it’s a win win. We live near the beach now and taking the Vespa on quick jaunt and being able to park anywhere is amazing. The summer will be extra fun.

    2. The 7 minute mile makes me laugh. During COVID lockdowns, I was working way more than I should while adjusting to the “new normal”. I was previously a 10-12 hour a day kind of person but because of guilt of working around kids and not realizing I was more efficient without the water cooler drama, I ended up working more like 16+ a day. Add that with more liberty to drink and take on poor health habits, I felt like my body was in decline. For no real reason one day, I decided enough if a enough and logged out of a meeting, drove to a local highschool that has a large looped road – roughly 1/2 mile loop. (I couldn’t use the track because it was closed for COVID). And decided to test my fitness. I went threw on some running shoes didn’t do any warm up and just started my watch and ran as hard as I could for a mile. I ended up running a 6:03 mile. {side note, I used to be a sub 4:30 miler for context} I hadn’t run in months prior, I was easily 15-20 pounds above my fighting weight – COVID lifestyle binge. It felt amazing, to just break out of the cycle. The next day my legs hurt and my body hurt, but I knew that COVID was taking me the wrong direction. So, from that day on I’ve been working out more regularly – I cycle, erg, run, and lift 6 days a week. I’m back down towards fighting weight, still some to go.

    All the while, my stocks have exploded. I took a new higher paying job. I sold my house, and bought a new one that is 3x the SF (COVID would have been so much easier working and living in this house with the young kids). And my life is getting much better! Why not be in the best shape of your life to enjoy it. I want to live healthy forever!

    1. Nice gift! Always nice to give a gift that you can use and benefit from.

      A 4:30 mile is fast. Given that is your baseline, it’s time for you to get to at least 5:30. Everything is relative!

  20. Thanks Sam. Love the positivity. Been dusting off the old cobwebs too! I’m down here in Orange County and people are spending like there’s no tomorrow. Feels like a combination of HELOCs, stock trimming, and people that have been packing it away for a while. Can’t take it with you!

  21. Ms.Conviviality

    Already spent our YOLO money back in November. With all the money saved from having no social life or travel and my husband’s booming handyman business, we bought a fixer upper. The house gave us something fun to work on since we couldn’t go anywhere anyway.

    Regardless of our savings goals, we always say yes to group get togethers and trips, whether with family or friends since these take effort to coordinate so they don’t happen too often. These are the moments we work so hard for so it doesn’t make sense to turn them down. First post-pandemic group trip will be hanging out in a NH cabin with 4 other families this August.

  22. finis temporis

    Love the comments and your reflections Sam! Also love the pace of the posts! You are on F.I.R.E. lately! (pun intended!).

    I’m 54 and considering a career change. C-level position a decade plus. The last year has been crushing both in terms of work and family (2 career couple, 2 year old and no real child care b/c of COVID). I’m toast.

    Your reflections on the Zeitgeist really helped me process what I’ve been thinking. I hope others are thinking it as well. I’m kinda expecting half of the leadership at my company are all going to walk out the door too.

    If I’m right (and you are right) what the hell happens to these companies – especially when money isn’t what’s driving people’s motivations like previous years.

    1. Ah, I think there will ALWAYS be a hungry young gun waiting in the wings to take a leader’s spot. Don’t worry about capitalism. The desire for money and power will never end!

      Just make sure you stay invested in the most money-hungry and powerful companies if you want to grow your wealth without having to work so much. It’s sad, but true. Hard to fight capitalism!

      1. Two weeks ago, I took my six person family
        on vacation. First class for a 5 year old. Two beautiful rooms at a four star hotel and spa. $1300 for one week car rental. Immoral. Hope they go bankrupt like Hertz. We ate wonderful food and did everything we wanted. Cost $14,000. Sold four shares of Amazon and rest from cash. I did not work for this money. My investments paid for it. This is the joy of investing. Next trip to Hawaii. Go Amazon

  23. As always, great info Sam! Thanks for sharing.



    I especially took this paragraph to heart:

    ‘My true hope is that all of us reprioritize the things that mean the most to us during the YOLO Economy. Chasing prestige and status is a low priority in the YOLO Economy. Instead, we should work on improving our health, our relationships, and our purpose.’

    1. Paper Tiger

      That was my favorite as well, especially that last sentence. I retired 6 years ago at 57 and I’ve been focused keenly on all 3 of those priorities, “health, relationships and purpose.”

  24. “If I had died in Mumbai before being able to propose I would have been pissed” cracked me up. Thanks.

  25. I don’t. The jobs you mentioned, venture capitalist & hedge fund managers, are clearly mobile. But there is a large percentage of the work force that prefer work directly related with a product or service. Industries like construction, manufacturing, and K-12 education allow for less mobility. In exchange, you may get more meaningful relationships generated through, sense of accomplishment when seeing a tangible product (like a completed building you worked on), etc.

    Just because the lifestyle is accepted does not mean it is desired by all.

  26. You have such a great positive attitude in this post. And really clever idea on calculating and spending one’s boot. I don’t really have much I want to spend on at the moment, but am looking forward to more freedom this summer. I would love to go to a spa in the mountains and have a nice summer vacation.

    I love what you said here:
    “My true hope is that all of us reprioritize the things that mean the most to us during the YOLO Economy. Chasing prestige and status is a low priority in the YOLO Economy. Instead, we should work on improving our health, our relationships, and our purpose.”

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