Overcoming The Downer Of No Longer Making Maximum Money

Do you know what is really hard? Deciding to walk away from a whole lot of money in your prime. If you decide to retire early or take a lower-paying job out of joy, you must accept the death of your maximum money potential.

Over the years, many readers looking to retire early or do something more fun but less lucrative have found it difficult to walk away. After all, working for just one more year will boost your savings that much more!

Then ten years go by and they regret sacrificing so much time for money. Time lost with friends and family. Journeys not taken. Businesses not built. Passions not followed. The list goes on.

If you don't enjoy your job, this regret of pursuing more money will sting even worse. Therefore, make sure if you choose money, to make the most of your free time.

This post will share how you can quit the pursuit of always making more money to live a more fulfilling life. Because once you get to your target stretch income, the joy won't last for more than a month. You'll then naturally try and make even more money.

The cycle never ends until you learn how to break it.

Breaking The Golden Handcuffs Is Hard

At age 34, I was making a base salary of $250,000. Come year-end, my bonus would range between $0 to $500,000. Instead of suffering from the one more year syndrome for one more year, I decided to quit the money by negotiating a severance instead.

If I hadn't left my job and averaged a realistic $500,000 a year in total compensation since 2012, I would have made $5 million by now. And if I had gotten regular raises and promotions, maybe I would have made more than $7 million after ten years.

Damn, perhaps I should have stayed in finance after all!

The more you make, the harder it is to walk away. Conversely, the less you make, the easier it is to take more chances.

I told myself back in 2011 that if I didn’t leave soon, I probably never would break free from the golden handcuffs. Many people who dislike working in finance, management consulting, and big tech after a while have this same problem. It's hard to drop your maximum money potential.

However, if you’re unhappy with your current situation, as I was, you must find a solution to overcome the desire for more money. Once you make enough to have your basics covered, more money truly doesn't bring more happiness unless you enjoy what you do.

How To Be OK With No Longer Making Maximum Money

Everybody has the ability to make a certain amount of money. Income has a range that usually increases the older you get.

Rational people are also realistic with how much money they can potentially make. If you decide to work for the government, you know your pay will be within a very tight band. Alternatively, if you decide to become an entrepreneur, your income upside is unlimited.

Let me share with you the steps I took to be at peace with no longer trying to make maximum money. In the process of walking away, I also lost my title and became a nobody. For some, walking away from status and prestige is even more difficult than walking away from money. We all want to stay relevant somehow.

To clarify, this post is not so much about early retirement. It's more about saying no to a promotion or a job transfer that requires more work for more money. It's also about taking a new job that brings you more meaning, but doesn't pay as well. Early retirement is an extreme example that isn’t for everybody.

1) Envision What Your Life Would Be Like Making More

The easiest way to imagine how your life would be different if you made maximum money is to analyze the life of your boss.

The two most observable things include their house and car. The type of car your boss drives may be misleading given they may drive their dough car to work and leave their show car at home.

However, when you make a lot of money, the one thing you tend to splurge on is your home. After all, we're spending a lot more time at home post-pandemic.

Find the address of your boss's home and ask yourself whether this is the type of home you aspire to own. Just be aware your boss may be a Financial Samurai reader and purposefully downgrade the features of their home to stay more stealth.

The next step to discover what life would be like making more money is guessing whether your boss has a happy home life.

Is s/he single, happily married, or bitterly divorced? Are his or her kids well-adjusted or in rehab? Do his or her kids attend good schools? Are they still living at home as adults because they were neglected by workaholic parents? Obviously, these are judgement calls you must make.

The final step to deciding whether you want to make maximum money is to rate your boss's overall happiness at work. Use a scale of 1 – 10 after deciding what your rating is.

Is she coming into work and leaving at a reasonable hour? Or is she constantly burning the midnight oil? Or maybe she's living the dream working from her vacation home in Hawaii while commanding you to work in the office. If your boss is making big bucks while hardly working, then you will certainly be more motivated to stay on!

After several years of working together, you should be able to get a good idea of what your boss's lifestyle is like. You must then make a calculated decision as to whether your pursuit of more money is worth it.

Not An Exact Science Analyzing Your Boss's Lifestyle

Of course, you won’t necessarily replicate your boss's lifestyle. Maybe he is generally a moody and miserable person. And maybe you are a jovial person who takes a more optimistic outlook on things. However, a lot of stress in life comes from your responsibilities at work and the activities you do to make money. Therefore, be realistic with your comparisons.

Personally, I liked my immediate supervisor. She was the most hard-working and optimistic person in the office. Go Kathryn! However, she didn’t have jurisdiction over my pay or promotion. She was more of a figurehead given we worked in a satellite office. My career was determined by my bosses in New York City and Hong Kong.

My boss in NYC was actually the same level as me, Executive Director, but five years older. I knew he had to get promoted to Managing Director first before I could. Therefore, at minimum, I had to wait another three years. That was too much time to waste.

My NY-based boss was an OK guy. But he was not charismatic or inspiring. He also looked very unhealthy, which is something that disturbed me. I was paranoid that if I worked as long and as hard as him, I might one day look and feel like him.

There are many stories of relatively young people dying from heart attacks in high-stress work environments. Further, I was already suffering from plenty of chronic health issues due to all the stress.

I had the belief the richer you are, the fitter you should be because you can afford to eat healthier foods, hire trainers, and so forth. Therefore, his poor health made me wonder whether our work was somehow taking years off his life. If I worked until his age, would my health also disintegrate? I became a little paranoid.

There is no point having a lot more money if you are unhealthy or die young. Having to work for 5 to 10 more years to potentially make 100% more was no longer worth it to me.

2) Calculate The Minimal Amount Necessary To Be Happy

The minimal amount of money necessary to be happy equals being able to cover your core living expenses: food, clothing, shelter, healthcare, and children (if any).

Some researchers believe once you make over $75,000 a year, your happiness no longer increases. Inflation adjusted, that figure is about $100,000 today. $100,000 might be great for someone living in Des Moines Iowa, but it’s not that great for someone living in an expensive coastal city. Adjusting for the cost of living is important.

In 2012, after carefully analyzing my income since graduating college in 1999, I decided that making $200,000 a year was the ideal income for maximum happiness living in San Francisco or Honolulu.

My investment income was generating about $80,000 a year, my wife was making about $120,000 a year, and I was earning some supplemental online income as well. Thus, I felt taking a risk and leaving work behind was OK in 2012. Worst case, I would go back to work after a couple of years.

By the time my wife retired in 2015, we were able to generate closer to $150,000 a year in passive income. Although we were $50,000 a year short, I had confidence that we'd eventually get to $200,000 and beyond if I regularly reinvested my growing online income.

Analyze your budget for the previous three months to calculate your core living expenses. Treat your analysis like a pop quiz since. For the next three months, observe whether your core living expenses truly are enough to make you satisfied. If not, keep spending a little more each month until you find that perfect minimum monthly expenditure.

Now work backward and see whether your existing capital and supplemental income activities can cover this annual lifestyle expense. If it can, then you can take things easierl. If it can't, then keep on saving away until you can get there.

Be Careful Not To Overestimate How Much You Need

Since leaving work, I realized we overestimated how much we actually need to be happy by about 30% for the first five years before we had children. It's as if we forgot that after we retire, we no longer need to save for retirement. But we calculate a savings rate into our retirement income anyway since we're so used to the habit.

If you have a net worth equal to 15-20X your average annual household income for the last three years, you can probably retire comfortably. If your net worth is equal to at least 40X your average annual expenses, you should be able to retire as well.

I wouldn't use 25X your average annual expenses as a multiple to declare financial independence anymore given how low interest rates are today. The proper safe withdrawal rate is lower today than in the 1990s. Further, unexpected expenses pop up all the time, not to mention the occasional bear market!

However, these multiples are used for those who want to retire and not make ANY active income ever again. This article is about how to walk away from making your maximum money potential, not all money.

Therefore, if you have enough passive income or capital to cover your core living expenses, you should better be able to overcome the pursuit of maximum money. In other words, we're talking more Barista FIRE or Coast FIRE where work is more flexible.

3) Find More Joy And Purpose In Something New

If you find something you'd be willing to do for free, it is much easier to shun making maximum money. If you're making a lot of money, but not helping anyone, you'll eventually lose interest. Your soul might start hollowing out as well.

Let's say you're making millions as a senior executive at The Coca-Cola Company. Your company is producing artificial products with excessive amounts of sugar that are hurting the health of billions. The ingredients in the products are creating more diabetics and creating a larger burden on the healthcare system. Clearly, you're not helping the world.

However, you may trick yourself into thinking you're doing good due to a charitable foundation Coca-Cola or you have created. You can tell yourself the means justify the ends in order to take care of your family. But deep down, you know that greed is what's driving you to get more people hooked on sugar. The same goes for working at tobacco companies and maybe some social media companies too.

At the end of the day, you want to feel good about the product or service your company is producing. Once you've accumulated enough capital to cover your core living expenses, it's worth trying to switch jobs if you don't feel proud of what you do.

Experiencing A Wake-Up Call In 2008

Once the Global Financial Crisis hit, I no longer felt good about working in finance. Even though my job had nothing to do with the housing crisis since I worked in international equities, it still felt bad to be part of the system.

Yes, there is good in helping pension funds and retirement funds grow so that people don't have to work forever. However, after 13 years, a career in making money from money wasn't satisfying. So I left. I wanted to produce something instead.

Financial Samurai made very little money during its first couple of years. But I kept writing for several hours before and after work because I was having fun. Making money online wasn't the primary goal. Expressing myself and connecting with others was and still is.

As the site grew, I could see the reward in helping people solve their financial dilemmas. Empowering people gave me purpose, therefore I have continued until this day. The kind comments and supportive notes are supremely rewarding, way more than any amount of money can provide.

Thank you letter to Financial Samurai to encourage you to quit maximum money making potential

4) Make Sure You Actually Win Back Some Time

If you choose to walk away from maximum money, make sure you gain back more time in your day. Not only should you gain back more time, you should also make sure you're less stressed. Don't just go through the same motions with your new occupation. Be very purposeful about how to utilize your extra time.

One of my friends left banking to become a pastry chef. She went to baking school for a year and got a job as a junior baker at a restaurant. She went from making ~$300,000 a year to $15/hour standing on her feet for eight hours a day. The joy of baking the yummiest desserts quickly disappeared.

She told me, “If I'm going to constantly be yelled at, then I might as well go back to banking!” Two years after quitting banking, my friend returned. She's been back ever since.

Giving up 80% – 90% of my income was painful at first. However, being able to have 100% control over my free time made me incredibly happy.

More importantly, my chronic back pain, TMJ, and allergies started going away as well. My TMJ was so uncomfortable, I once paid a dentist $700 out of pocket to drill divots in my rear molars to provide jaw relief.

The health benefits of early retirement are priceless. The recovery in my health made walking away from maximum money much easier. More time is already more valuable than more money. The combination of more time and better health made quitting the money that much more of a no brainier. However, I didn't really appreciate the health benefits until about a year after leaving my job.

And once again, it was the noticeable deterioration in my mental and physical health during the pandemic that necessitated a need for a sabbatical.

I discovered what it was like to make more money online because I tried, but it didn't make me happier. Instead, it sucked me back into the never-ending cycle for more, more, more.

5) Try To Escape With A Win

Leaving a high-paying job with a severance package is a must. It is very common for high-paying jobs to come with some type of stock compensation or deferred compensation to keep you locked in.

A severance package helps pad your new lower compensation so the transition isn't as jolting. With a smoother income transition, it will also be easier to accept making less money.

By negotiating a severance package, I was able to make the same amount of money had I stayed for the rest of the year working. This felt like a huge win.

The severance package kept paying out a livable income for five years total. As a result, I wasn't as stressed as I should have been in my mid-30s. Further, I didn't feel rushed to make money online.

Three years later, my wife also walked away with a severance package in 2015. She had a lot of doubt she could negotiate one, even after I negotiated mine. But after much coaching, we were able to come up with a win-win scenario. She felt like she had won the lottery!

Other wins may include having your company pay for your MBA, parental leave, or a sabbatical before you leave. If you like your company, another win may include getting reassigned to an easier role with less of a drop in pay as you would have expected.

It's easier to walk away from maximum money when you are winning than when you are losing. Think about an NFL player retiring after winning a Super Bowl or a tennis player after winning a major. When you're losing, there's an inherent desire to prove to yourself and to your detractors that you can still succeed.

Knowing when to quit is as important as knowing when to keep on going. If you keep on grinding at something that is no longer worthwhile, you're robbing yourself of a better life.

Making Lots Of Money Will Not Make You Happier

One of the goals I have from posts like the ones below is to make you question your pursuit of making maximum money.

In big cities such as New York and San Francisco, where I have lived since 1999, I meet people all the time who are miserable making multiple six-figures.

They went to good schools and feel like they have to follow traditional industries that pay the most. If not, what will their friends and family think of them? I'm assuming many of you reading this article fit the profile as well.

After I started focusing more on entrepreneurship, I began meeting people making millions a year. But they seem to have even more issues than the six-figure crowd!

One went through his third divorce. Another is constantly annoyed at dealing with HR issues given he's the big boss. Yet another is dealing with a lawsuit that wouldn't have happened if he wasn't so rich. And another has been so stressed out by the markets he hasn't been able to play tennis for six months due to a psychosomatic injury.

As you climb up the income stratosphere you simply start comparing yourself to a new set of highly-accomplished people. Just like making more money, the comparison never ends.

Make The Effort If You Feel Like Something Is Wrong

I know it’s hard to quit the money, but you must try if you are not happy. No matter how much money you make, if you don't do something meaningful, you will eventually fall into a pit of despair. You might find yourself becoming more irritable, more moody, and more cynical.

Please calculate the minimum amount required to cover your living expenses to get understand your base income need. Then pursue something else that brings you joy. Stop moving the goalpost by appreciating more of what you have.

Although I left behind millions of dollars in finance, I gained back time. And if time truly is priceless, then giving up lots of money is no sacrifice at all.

Readers, are you pursuing your maximum money potential at a cost to your health and happiness? If you have been able to quit the money by taking a lower paying job, retiring early, or changing fields, I'd love to hear how you did it.

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76 thoughts on “Overcoming The Downer Of No Longer Making Maximum Money”

  1. Hi Sam, I appreciate this article, I think about this topic every day. I am 39 and am approaching the $3 million mark in the next week or two, most of which I have earned in the past few years. I trade low latency arbitrage strategies that I’ve discovered myself and haven’t taken a day off since 2019, mainly because I have been figuring that these opportunities won’t be around for very long. The cost of even not trading for a day feels unbearably high, yet the constant work and pressure are making me miserable and taking a toll on my health. If I knew I could come back to the market after a year or two off and have this waiting for me, I’d take a long vacation immediately. I had told myself earlier that $2.5 million would be enough. Now with inflation, I have my eyes on $4.2 as a safe exit point a year from now, but my real fear is that as I earn more the cost of walking away will become higher and higher to the point where I’ll wake up one day in my 70s with a fortune and realize my life passed me by. I think the hard part is putting a dollar value on what your time is worth. I don’t have a family so it’s not like I’m missing time that I could be spending with my kids as they grow up, but still, this is time I will never be able to have back again for any price. I appreciate hearing how you were able to walk away and I hope I will be able to make a similar decision before too much of my life goes by.

    1. This is the exact question we must all answer but with different variables (kids, no-kids, married, single, dependents, aging parents, paid off home, mortgage and the list goes on). Common denominator is that we only have so many years and how to spend them vs incremental earnings and the flexibility created by more $$$ and the wall of safety that we perceive from each dollar bs the drain it creates to grind on

  2. Great article. As a miserable (albeit highly paid) Corporate lawyer living in a very expensive city (Hong Kong), the struggle between exploiting my max earning potential for a few more years vs quitting for a less intense job in exchange for a ~50% pay-cut (in pursuit of happiness!) is a daily one.

    I’m far from FI unfortunately but trying to get closer with insights afforded by great FI sites / blogs like FS.

  3. Thanks Sam, your article was very timely. I just finished writing a draft email declining the opportunity to be on a shortlist of candidates to replace the company’s CEO. My current position allows me to spend a lot of time with my wife and two young children while making approx. 600k. It was actually an easy decision to make but your article helped confirm the decision was correct. I am working on a way to get out (early retirement), not to move up.

  4. Thank you Sam! This message I exactly what I needed to hear today. Although I reached FI in my late 40s, and promptly left my c-level income to enjoy freedom and creative pursuits, I admit it’s hard to quit the mindset of maximizing my earnings.

    I continue to get recruiter calls about CMO jobs, and even though I love everything about my new passion project helping others advance their careers to make more money, my first reaction is to explore the role/company and compensation oppty (before I get my senses and politely decline).

    Hopefully this instinct will go away completely someday… but until then, posts like yours offer a great reminder that gaining back time is priceless!

  5. In my career so far of 20ish years, I’ve found the no. 1 factor for work happiness is the PEOPLE you with with. The work, commute, pay etc. are all things you can make adjustments with, but if the people suck it will affect you the most in terms of stress and unhappiness.

    I’m blessed that I haven’t had the Sunday evening blues for almost a decade because I love the people I work with!

    1. That is a great point. You are blessed! More than the money are the people you get to work with is so true. The finance industry is cutthroat, a dog eat dog world. Eventually, most people want to get out.

  6. I don’t understand the premise. I understand that surveys are not exact, but I am considerably more happy making $500k then I was making $150k several years ago. For me money is security and freedom. With the other 350k I:

    1. Joined a nice CC (I love to golf/tennis).
    2. ventured into real estate investing – I didn’t make enough before to do more than max 401ks
    3. no longer stress about buying a car or appliance or major home repair.
    4. stay/live first class on nice vacations instead of always looking for “deals”
    5. saving $200k a year for early retirement.
    6. Increase giving
    7. Simply treating my grown kids a bit lavishly at times.

    If you aren’t considerably more happy making 250k or 500k than 75k, for instance, then it seems like maybe you have no hobbies or no zest for life? Maybe the “more happy” is “less stress”? To me less stress = more happy.

    From the standpoint of “early retirement”, now that many of us have banked alot, perhaps 75k in retirement doesn’t hinder our enjoyment of life. But if you are starting from scratch I seriously doubt the majority of people would claim they wouldn’t be more happy making 250k than 75k.

    1. The premise of the article is exactly if you are no longer happy making more money, how to break free to do something else that will make you more happy.

      If you have found a job that you love that pays well, then by all means keep on doing it. That’s the jackpot scenario.

      What do you do and how long have you making the $500,000+ a year?

      1. Engineering with a consulting firm. About the last 10 years. Before that made about 150k. My job satisfaction – the work itself – hasn’t really changed, but I am much happier overall coming to work in my job BECAUSE I make so much more doing it. It’s enough of a difference to tip the scales and providing greater freedom and choices.

        I guess I was just simply questioning the premise that making more than 75k won’t chance happiness. Assuming you stay in the same job and do the same thing, wouldn’t someone making 500k be substantially happier than someone making 100k? Maybe I am rare in that. Seems obvious.

        Of course, if you hate your job so much that no amount of money would make it worthwhile to stay, then I would say just try to coast as long as you can. But I think those situations are outliers. I mean really hate the job or it is harming you. like yours did. I can see the financial industry being that way.

        1. Cool. How old are you? I really got bored of doing the same thing after 11 years in a row, so I had to change.

          The $75K figure is more like $105K now, inflation adjusted.

    2. All else being equal, yeah, I think most people would enjoy life more and be less stressed if they made more money. It sounds like that be the case for you. But for a lot of people (including myself), the nature of your job/work changes as you make more money and sometimes in ways that make you less happy / cause more stress. Sure- outside interests, family, friends and hobbies help, but even they can be overshadowed by the wrong career. I think it also depends on your personality- some people could work in a snakepit for years and wouldn’t bat an eyelash as long as they were maximizing their income. Others are more affected by what they are doing and who they are working wiith for 40/60/80/100 hours a week.

      1. Understood – IF you absolutely despise your job and/or the stress sends you to the doctor, then yes can’t relate money to happiness.

        Try not to fall prey to the fallacy that is the puritan ethic. People think because they get paid more they must work more hours. You can provide value, and “only” work 40 hours a week. IF you dislike your job but get paid great, work less and see what happens? Another benefit of saving and having financial freedom is you can just work as much as you want., let chips fall where they may.

  7. I had a lot of stress in my last job that used to give me literal nightmares. I’d dream about getting yelled at by clients and not knowing how to fix certain problems and the like. It was rough. But there were some aspects of the job that I really liked that kept me going for a long time.

    I was motivated by my superiors for many years. They had better tasks, authority, autonomy, and better pay that I wanted. That definitely propelled me forward to put in my hours and dues in order to get their titles. But once I reached a certain title, I realized the next rung up the ladder would be my boss’s role. Not only was that many years out of reach, it was also a role I sincerely didn’t want. Sure more money would have been nice, but I truly did not want his specific responsibilities and stress.

    That and too much stress in my last role was a big reason why I read your ebook How To Engineer Your Layoff. It took a while, but I was able to use it as a roadmap to escape and I’ve never been happier. So thank you Sam!!

    1. So wonderful to hear! So far, I don’t know of any better professional feeling than retiring early with a severance package.

      I’m sure retiring at a normal age with a pension feels wonderful as well. But being able to leave your job much earlier than 60 with a severance package has to be better due to the time it buys.

      People don’t have to retire early. But I hope we don’t settle on our occupations and find something we truly enjoy doing.

  8. Wow Sam, the part of watching your boss to see what your future could look like is eery, and a future I do not want. My boss texted me over the weekend while I was golfing, and he had been up since 2 am working on a project. I know the project he was working on, and it was really kinda ‘busy work’, so I’m not sure if he just texted me to make me feel guilty or what. Anyway, I don’t see his life as the future of mine. I’ll take unemployment before that.
    Very inspiring post as usual!

  9. Shortly after accepting a job in Silicon Valley, my manager-to-be informed me that I made more $ than he did. I took it as a compliment of my negotiation skills (naively), but I should have taken it as a red flag that I was about to begin an uphill battle being managed by someone who felt slighted and/or jealous that would end up standing in my way instead of helping me continue to soar. I was at maximum money. More than I’d ever imagined and actually working my dream job. But, the jealousy continued, manifesting itself mostly as extreme micromanagement and performance ratings that were fine but left me with no significant pay bumps especially compared to the efforts I was putting in; it was clear that I was being managed around this person’s next promotion which, from my optic, was a long ways away. A career coach told me years ago that bad situations at work will change because bad situations are not sustainable. The question you have to ask yourself is, can you wait for that change to happen and is the wait going to be worth it?
    After a couple of years it became apparent that this situation was not going to change soon enough. My contentions regarding my manager’s misinterpretation of the performance review system were not met with any substantive rebuttal (mostly anger) or any useful changes so I decided to leave.
    Certain parts of my industry are fraught with upper management roles that are not attainable for folks who do what I do. It just tends to trickle up to a certain type of engineering and hardly anyone in my industry has a degree, let alone an engineering degree. Which is to say, I agree with your advice on assessing your manager’s happiness/lifestyle/etc. and I’ve given the same advice regularly, but in my case, I would never have qualified for my manager’s role. I would have had to prove my role needed a different manager and that I was the person for that new role. My manager seemed largely discontent with his perceived place in worklife. In all honesty I kept seeing indications that his role and team were largely redundant after a couple of acquisitions brought in redundant teams.
    Leaving my dream job after a few years was actually harder than selling my company after 20 years and it took longer to decompress from thinking about work than I expected (similar to GoCurryCracker’s experience). The pandemic didn’t help but I still believe I’m healthier and happier for making and executing that decision. Big thanks to you, Sam, for your articles/stories that helped me reframe success and sort through the multifaceted decision.

  10. Perhaps the most beautiful aspect of FI is not the ability to retire… but the OPTION to retire, downgrade, stay on, or start a business. Money give you options, not happiness.

    I’m on track to FI in 14 years. In my mind, I’m going to quit work and coach my child’s sports team full time. But who knows? If I’m still loving my work, I might stay on. I’ll definitely use more of my vacation time though.

  11. I’m almost 50 and recently left a low 6 figure salary to pursue a much lower paying job but one that will suit me better and should be more enjoyable and meaningful. Financially we’re fine since my husband continues to work. Our retirement finances are good. I do some part time work, and am going to school but still can’t enjoy the down time I now have. I feel guilty for not making more money even though we’re financially secure, and live a simple life.

  12. Very informative!

    If I read this earlier on, at a time when I had to turn down a big job despite the desire to make more money I am certain that I would not have struggled with approach avoidance conflict.

    I am happy though that I got to read this at a point when do what I love for much less.

  13. Great article, Sam, I think this is exactly the mindset that I also employ in my path to financial independence.

    The one catch to the mantra “give up maximum money” is that it’s impossible to know when you’ve achieved maximum money. I know your point is more so about giving up maximum money once you’ve saved enough to cover your core expenses, but what we all struggle with is the knowledge that if we save up just a little bit more than that buys us even more flexibility and optionality. I know that once I give up maximum money I likely wont regret not having to work a full time job that isn’t as fulfilling, but I also know with 100% certainty that I will regret in old age not having saved enough if something happens (e.g. disability, unexpected medical expenses, financial shock). It’s very difficult to go back to work for maximum money after having already quit. The dilemma is striking that balance. The point I’m making is that if we know we’ve already hit the point in our lives of maximum money, then the decision on when to quit is easier, but most people don’t know when they’ve hit the peak and will therefore feel inclined to continue saving, perhaps longer than they need to.

    1. I think the maximum money range is relatively known for most people with normal day jobs. You can estimate what that Max Money is to a reasonable degree after your promotions and years of experience.

      It’s much harder as an entrepreneur bc the sky is the limit. And as an entrepreneur, you can literally do nonstop work to try and make more money.

  14. I have struggled with this issue a lot since my retirement last year at age of 60. I was making over $600k per year but the stress really got to me and I had nightmares, depression, anxiety and health issues.
    I was not happy for years but kept on pushing myself to go one more year then one more year….
    Wife is still working and make great money so we have been able to continue to save because our expenses are less than her take home pay.
    Our net worth is 8 digits so we don’t need more money, and we have very modest life style. However, giving up a big fat salary and a fancy job title has been more challenging than I had imagined.

  15. I retired in 2016 at total compensation of $140k/year. Since then, my wealth appreciation — equities 80% and RE 20% — has been climbing and is about to hit $1m/yr. I think one can eclipsed W2 income and continue to grow “compensation” and not lament a damn thing.

  16. I think about this issue myself, as I am investing in dividend stocks with the intent to retire abroad in about 5 years.

    I’m 25 with my own business that is location dependent, so moving abroad would require me to drop the business.

    I figure that $1,000 per month in dividends will cover my core expenses, but dropping down to that level of income may be a shock. I’m nearly certain that I’ll want to continue building my wealth beyond this point even though I may be able to live comfortably on this amount thanks to geo arbitrage.

    1. At 25, I keep grinding away hard for the next five years to see how much well you can really accumulate. Don’t waste your energy not trying your best to build your capital base.

      You’re older self will thank you. I promise you that!

  17. Enjoy your sabbatical, Sam! Health and family are most important. It sounds like you’ve made the right decisions for you and your family when you left ibanking. If you stayed on, maybe you would’ve had a whole head of white hair by now!

  18. I left NYC half way through the pandemic to live in a (still high cost of living) beach town outside of commuting range.

    I have to say it’s given me a lot of perspective. My wife and I never thought of leaving the city in 15 years, but now don’t really long to go back.

    We both work in financial services and the pandemic has been a big eye opener.
    Sitting in my 400 sq ft attic home office on zoom call after zoom call, but also dreading returning to the elbow to elbow trading floor where that 400 sq ft will be populated by 20+ other people blabbing away all day.

    Work hours have managed to expand to fill the void left by lack of commute and social life.
    Will be interesting to see how things readjust on return to office, but either way my wife & I have a totally different perspective and 10 year plan than in 2019.

    I’ve mentally run the numbers repeatedly walking the beach thinking of various scenarios.

    a) If we rent out city condo it would cover all our monthly costs there & probably produce a capital loss after depreciation. We would continue to accumulate equity, while putting the equivalent of 25% of our after tax income into savings. At some point it will even produce positive cash flow between now and when the mortgage is paid off.

    b) If we just sold the condo in the city, it would save us about 30% of our after tax income. We could also use the condo equity to pay off a chunk of the beach house mortgage, probably bring our total cash burn rate down by 35%..

    Either option leaves us in a position to increase our savings more rapidly and/or take on lower stress/pay jobs. Earning less would also reduce our tax bracket so our after tax income wouldn’t necessarily go down proportionally.
    Whether that happens now or later, we realize that the idea of retiring in the metro area was always insane, and we can have a great life out here at half the burn rate. This also means being able to retire earlier..

    1. A pandemic blessing for you guys to figure out a new path to life and financial independence!

      And you guys leaving also makes it better for those people who stayed behind in New York City. So it’s a win for everyone.

      I’m personally excited for a big city living again, and I’m trying to buy in New York City and more in San Francisco for my children. I think there’s gonna be a rush back with a lot more opportunities than before.

      I want to get a burger on a popular street in the northern part of San Francisco after a softball game last week. And it was ridiculously packed inside and outside for all restaurants with no masks.

      Best of luck on your new more relax lifestyle! And don’t work too much while at home.

  19. After leaving “maximum money” about 5 years ago and “near maximum money” about 2 years ago, I’ve been trying to find that elusive situation where I can coast a bit but still make some money. I’ve been doing some contract work in my field of expertise and I’m slowly coming to the conclusion that it sucks almost as hard as a permanent job, and for less pay. When someone hires you for a 3-6 month contract, the unspoken expectation seems to be that the only days you will take off are weekends and holidays. After all, when the contract is up, you can take as much time off as you want, right?

    The problem with that is that during the contract you actually have less flexibility than you would in a full-time permanent position that comes with a PTO bank. So I’m starting to think that, at least for me, semi-retirement is just not worth it. Need to either put both feet back in the workforce or none.

    1. Fascinating feedback about working as a freelancer. Thanks for sharing. What I did for about three months was take up multiple freelance clients $10,000 a month. It was really great money, but it wasn’t sustainable as it became too much work.

      Perhaps try to raise your consulting rates dance right in your contract about the amount of hours and stuff you plan to do to create more barriers?

      Or what about taking the next step and letting go of trying to be near Maximum money at all? That’s actually the whole point of this article. To let go.

      1. Sam, I have already let maximum money go, whether I like it or not at this point. My point is that I haven’t been able to find a sweet spot between near maximum money and fully retired. For me at least, it seems like I need to cut the tethers to the work life entirely or just go back and get a full-time permanent job for a few more years. What I’m doing now seems to be giving me more overall time off, but less flexibility when I am working and less money, so the question becomes: why do it at all?

        1. Do you mean like the phrase “have your cake and eat it too”? Where you want to make near maximum money and not have to do any work?

          If you finally find the answer, let me know! The only solution I’ve come up with is trying to make as much passive income as possible.

          But even with about $300K/year in passive income, that’s not close to maximum money I could have made while working. But it’s enough to provide for a family of four in SF.

          1. Not really. It’s more about maximizing flexibility, not money. What I’m finding is that contract gigs seem to be every bit (if not more) demanding than permanent ones. Many of the companies need contract help because they are behind the 8-ball on projects, so when you come on you’re instantly working 50-60 hour weeks and taking any time off is frowned upon.

            The money is decent, but far from the maximum money I made previously. So it just doesn’t seem like working that hard is worth it. It’s point #4 in your article: Make sure you win back some time.

            1. I am facing a similar dilemma. Currently work a full-time job but am trying to come up with workable ideas to scale back and work part-time. Considered contracting but knew I’d run into the issue you mention here. Could probably find a part-time unskilled job paying $15/hour or something but what’s the point- might as well just fully retire. Trying to come up with the elusive part-time “lifestyle gig”, but nothing has come to mind yet. Considred blogging but I just dont have the wealth of insights/ advice/ knowledge in a particular area that someone like Sam does.

              1. I used to own a contracting (staffing) company and so I am very familiar with the Department of Labor rules regarding independent contractors. That was key in speaking with my client managers about their expectations because they typically thought they were paying for time when really they were paying for work or in other words, a project. They also didn’t usually understand that if they tried to enforce a work schedule as they did with their FTE’s, they were in violation of the law. One manager I (thankfully) didn’t have to work with would regularly pull a freelancer friend of mine into his office and close the door. He would then drill into my friend that he was being paid an absurd amount of money and the expectation is xx hours per week no matter what even though the contract said, in essence, *do this one thing for this amount of money regardless of the amount of time it takes*.
                I know, different industries have different circumstances but it was immensely helpful having the knowledge of the Dept of Labor rules at the ready for when the client started (inevitably) breaking them.

  20. I retired early…soon after I went to see a movie…I was amazed! I actually watched it attentively, the whole movie, and enjoyed every minute it! It was because for the first time in 20 years or more…I wasn’t distracted by thinking of issues at work.. Work had become a 24 hour a day 7 day a week endless mental task that distracted me from everything else that meant so much in my life. Early retirement was the best thing. I’m in the present now. I’m not distracted from taking in from my senses or thinking about my family and friends and enjoying experiences. It took great sacrifice over 3 decades to achieve. Completely worth it!

  21. Where does age factor in to the need for 20x income or 50x expenses? I would think (hope) it’s different for 55 year old versus a 35 year old?

    1. 20X or 50X expenses is a target anybody at any age can shoot for. If you can get to those targets by 40, you can retire earlier if you want. It’s just a goal. Everybody has different pension amounts, including social security, life expectancy etc.

      See: Net Worth Targets By Age

      If you’re 70+, you probably don’t need to have a net worth equal to 20X income or 50X expenses any longer.

      Also see: Two Retirement Philosophies Will Help Determine Your Safe Withdrawal Rate

  22. You left out the most important part of leaving the position in finance. I’m surprised you didn’t mention it but it might be an effort not to offend anyone. You never have to use the word’s “my BOSS” again in your life (you used it a lot in this article). Having to only answer to yourself and family is the biggest reason and it has nothing to do with money!

    1. Most definitely. But this article is more about giving up making maximum money, not retiring early.

      It’s about not wanting to be a manager any longer or accepting the promotion, but still working. It’s above moving from a frontline sales job with clients to a back office job without clients.

      Or taking a less stressful job that pays less money.

      1. I would be curious to hear from people who gave up maximum money (including a commute and travel)to pursue a local entrepreneurial venture and ended up still working a lot but felt energized everyday (including that energy and presence carrying over to family life which is exceptionally important) vs feeling drained at the end of the day from corporate nonsense and wanting to tune out with a double vodka.

  23. The Social Capitalist

    Great post FS. And I’m not sure if this is a refresher post or not but keep doing so- those may miss the target audience the first time but I enjoy seeing something that I may not have gone back to look for.

    I wrote a lengthy reply and realized. Most of it was just for me. So I’ll just boil it down to:
    – You hit the mark with knowing your net worth and choosing what you want to have or give up.
    – The social aspect is incredibly important.
    – It’s wonderful that some of us are afforded this luxury.

    Enjoy the family, don’t think that kids have to be the most expensive item ever (usually we make the much more expensive than they need to be), they need love and support, we are the ones who really want more than that. And use money as a tool as much as a cushion. Otherwise, it will make your ass fat, arms thin and mind small.

  24. I think when the question is “I’m either going to be worth $10MM or $5MM…” it’s not that difficult to walk away. Your life is not really going to be that different from being worth $5 mil, $10mil, or even $100 mil, unless you enjoy the really finer things in life.

    If the question is I’m either going to be worth $1 mil or $500k, I think it’s difficult to walk away because one has a large cushion embedded into it while the other doesn’t.

    1. I agree on it being harder to walk away before $1 million, or $3 million, the real millionaire threshold nowadays due to inflation.

      However, walking away from $5 million to put you to $10 million is extremely hard if the path to get there is really clear through work.

      $10+ million is the ideal net worth figure before retiring. But if you can get to $10+ million, you can most certainly downshift and focus on a job that provides tremendous joy and purpose. This combo is ideal IMO.

      1. David @ Filled With Money

        Ah, to work a job because you want to not because you need to. That is the goal :)

    2. I think it depends how you want to play the game though. If you can keep yourself living like a college kid then sure that makes sense. However, even with the intent of not falling into life style creep it still happens. Multiple kids means exponential costs. And the standard of living goes up because you want to provide for them. You also think what if your parents gave you $XYZ. Then you start thinking well just x more years and I can do Y. It’s not so much about having yourself covered that’s easy. It’s the feeling that you can help cover others if you just give more of your time. So it comes down to goals I guess. In regard to $5M vs $10M I’m not sure I agree. Those are kind of major milestones. In your $500k-$1M I agree would be harder to walk and Truly if you can walk with $500k then I’m impressed. I just envision a life without doubt or questions. And if a couple more years gets you to that freedom and removes doubt then just plot the timeline and go for it.

  25. Sam – I’m curious how much of the maximum earning you really gave up after leaving investment banking and ramping up the blogging. I know you’ve mentioned that it wasn’t about the money but with an audience your size I’d guess that the delta of you $250K base and $500K per year bonus potential isn’t huge if not in excess of what you left behind by now.

    No doubt you left all the stress and politics behind – let alone the horrible hours you’ve shared in the past.

    I know you only share certain numbers and never the full enchilada, but it would be interesting to all of us – I think – to understand the real delta.

    My guess is that this site is earning $500K to $1M+ per year.

    1. I think the real delta is better health or less worsening health.

      My first gray hairs were starting to pop out in 2011 and 2012. I also had TMJ and chronic back pain and sciatica. All those went away within a year after leaving work.

      And after a year of taking time off, I spend more time trying to make some money online. But the percentage time online was mostly fun and not business.

      But when the pandemic hit, I started to spend 40% of my time online trying to generate revenue to protect my downside and see what was possible.

      It was interesting to experience what maximum money potential online was like. But I don’t care anymore as things return to normal. I want to live unencumbered by money over the next couple of years at least.

      Time with my kids is #1.

      See: https://www.financialsamurai.com/reflections-on-making-money-online-since-2009/

  26. I retired slightly early but kept consulting for entertainment for the first five years. That let me grow our portfolio by over a million more dollars. Now I’m not earning at all but Social Security will kick in a few years from now and I’ll be at 100X net expenses. I’ve had several job offers in retirement that were unsolicited, ranging from $200,000 to one million dollars a year but I never seriously considered them. Not even the $300K offer for a job in Hawaii or a similar offer to work in the Virgin Islands. I don’t live in a coastal HCOL area so my magic number is about half of yours. Earning more money has zero appeal to me now that I’ve internalized the concept that I already have more than I need. Volunteer work is my focus from now on.

      1. Thanks for asking Sam, my kids are doing well. My MD son is two years away from getting out of residency, working like crazy and not earning much, but his wife is a doc too so they are doing fine. My other two are more upper middle to middle class earners but they are frugal and doing well. My wife and I have loosened up on spending a little buying a couple of nicer cars. We cancelled a very nice hiking trip in Switzerland so we’ll try to do that when the borders all open. We are also talking about driving to Alaska in our old 4Runner but that will require Canada opening up which hasn’t happened yet. My guess is we’ll continue to spend around $100K inflation adjusted and hand a lot of money down to our kids. They are very responsible with money so I don’t fear them going crazy with a seven figure inheritance some day. Still looking for a mentorship volunteer opportunity, I’ve sent out some feelers and think I’ll have some chances.

    1. That is likely an enviable position… having the stability where you don’t need to work and the ability to say no to a 1 year $1M contract. I’d say you have won the game so many times over! Hopefully all else is well in your world family and health wise.

  27. In 2014 I remember vividly sitting at a beautiful outdoor restaurant with a gentleman trying to retain my services. The piece of paper had written on it a $600k salary, bonus which would equate to $400-$500k each year, plus all the other perks that go along with a role of running a company. There was never a more liberating feeling than to graciously thanking him for the offer but let him know that I had to respectfully decline as we were just too far apart. To say he was shocked and upset is an understatement.

    Best decision of my life. I went from a 60-70 hour pressure packed life sucking job, to being free in my early 40’s. I’m so glad he didn’t put a number in front of me that really made me have to think, made it an easy call.

    1. Wow! Super impressive you turn down a $1 million offer back in 2014!

      60 to 70 hours of stress a week truly stinks. 20 hours a week is about all I wanna handle.

      You’ll have to share with us one day what exactly you did for a living to command that much. Thx

  28. This article really resonates with me because my husband and I made the conscious decision to do this exact thing once we had our family. He began to plan his move away from big law and into the government when our first child was born. I made the decision to be a stay-at-home mom. Both decisions were unpopular among our peers and we certainly don’t have the high dual income that most couples have in our big metro area, but we have enough. We cut out unnecessary expenses, prioritize saving and investing, and are diligent about saving pay increases. We’ve learned to spend money on needs and the three things we value most: our kids, our home, and simple vacations while saving up for bigger ones for special future treats. Looking at you Hawaii when our oldest is in high school! Since we don’t overindulge in luxury, we appreciate it more.

    Our family unit is very close. We have time for “mommy and daddy” school to supplement public school education and help our kids reach their academic goals, my husband and I have a strong relationship and friendship, and we have down time to recharge to keep us mentally healthy. The stress of big law income and dual incomes wasn’t worth it to us and ten years and three kids later, the trade-off has been worth it.

    I am starting to work part-time again, now that my youngest is headed to full-time kindergarten, but I’ve chosen something that gives me purpose. Teaching preschool is definitely not up there on the list of high incomes but I like giving kids a positive foundational school experience, especially since they missed a year due to Covid. And the flexible hours give me time to be home for my kids in the afternoons.

    1. I love this! And thank you for sharing.

      I actually play softball in a big law league, and the person I’m closest with left big law and joined Dolby labs as an in-house counsel. He says life is so much better being the client.

      I think it’s great that you’re going back to become a preschool teacher now that your kids are in kindergarten. So wonderful. Working with young kids and giving them love, support, enjoy is truly priceless.

      I’m going to volunteer back at the foster home once my son goes to preschool again at the end of August. All kids need our support!

  29. tokyorealestateman

    benefits of health are the best Sam-agreed-don t need to take mandated injections that have not been approved beyond the emergency protocols.

  30. I had that very thought process of trying to picture myself in my boss’ shoes. And it was clear to me that I didn’t want to be him lol. He was always stressed, I didn’t like the type of work he had to do, and he seemed comfortable financially but wasn’t blowing it out of the water. So the upside wasn’t high enough for me to want to keep going to get to his level. I went as high as I wanted to and then started to find a way to get out and take a new path. I’m so glad I did!

    1. Yeah, I remember your boss. Nice guy, nice living in the suburbs, but I doubt he made mega bucks, and doing all that business development stuff it’s not you. I’m glad you took a different path as well!

  31. I had to leave my job last year to take care of our kids during covid, my husband quit his job two weeks ago, we’d both worked for the same employer for 14 years. We’d been looking for a change for a while and will be traveling full time with our kids for at least two years, maybe more. We’re looking at it as more of a sabbatical than retirement, but we know we’ll never be able to earn the same money as we have in the Bay Area. We’ve always been pretty fugal and have been long term savers and investors and that has really paid off now, giving us the freedom and flexibility to live life on our terms. We have some rental property and real estate syndicate investments that will fund our living expenses whilst allowing our nest egg to grow at the same time. Life feels good right now that’s for sure!!

  32. I quit the big income from finance post accumulating >33x expenses. Trying to do something that is more meaningful and also brings income. It is a tricky balance to find something that pays a bit but that you love so much youd do it for free versus a high paying career that you dont enjoy. Im trying to find a route that has good pay and fun versus little pay and little fun.

    But I love the flexibility and autonomy of knowing we have enough. We have options, and we’ve learnt much from this website.

  33. Sam, your site is so invaluable and appreciated. Sincere thank you!!!

    In my profession (small business owner, rental home real estate investor) I’ve watched many of my “Big Hitter” peers work 12 hour days to be recognized as top producers in our industry. What I’ve also noticed is, the divorce rate and problems with their offspring are exceptionally higher.
    I was fortunate to go into business with another guy in my profession that happened to be 10 years older. We share office expenses and staffing expenses. We also cover for eachother in the office and trade days out of the office. Our motto has been, “It’s a marathon, not a sprint.” Sure we don’t win the prizes for most sales but I would put our individual Networth numbers up against any of the “Big Hitters.” The cost of divorce or problematic children, greatly outweighs the benefit of a little more money and no free time.

    1. Thanks for reading Jim and I’m glad to have helped somewhat.

      Yes on the marathon. It’s funny how life is both long and short at the same time. I feel the shortness more of life now that I have young children.

      Enjoy the balance!

  34. First of all, to you Coke,or Jull, or Exxon, or Investment Bankers, or any other employees of companies the woke class deem deplorable keep your heads high. This is America, where legal products and service jobs should be celebrated, not vilified. A job is a job period!!

    Thank you for not collecting enhanced unemployment benefits and keeping my Cokes cold, my vapes full of tobacco, my gas tank full, and my brokerage account flush!!

    1. ‘Merica!

      And to be clear, I’m not talking about the regular person trying to make money to put food on their table to provide for the family.

      I’m talking about the executive who is pulling down $10 million a year after already accumulating $100 million thinking that they are doing some thing good. Forget about it.

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