Your Window Of Opportunity Is Smaller Than You Think

While watching some competitive 5.0 tennis, a top 1% level, I suddenly started to reflect on why the window of opportunity that many of us have is smaller than we think.

From 2015 until 2021, I played at the 5.0 level. I lost 69.3% of my matches, but USTA's computer algorithm wouldn't drop me down to 4.5, so there I was, stuck in purgatory.

Today, at 46, I can no longer effectively compete at the 5.0 level. My right shoulder has lost about 15% of its strength and my eyes can't see the ball as well indoors or at night.

My window of opportunity only lasted for about 13 years, from 2009 – 2021. 2009 is when I began playing USTA tennis given the world was falling apart back then. But for the first six years, I had to get better and finally work my way up to 5.0. And then COVID took away one year of competition.

Let me share some more examples where we have less time than we think.

School Connection Through Coaching

For three years, I coached high school tennis. During this time, I developed a good relationship with the athletic director, who was also the head tennis coach. I figured, if my kids ever needed a friendly connection to get into the school, he would be it.

However, the AD retired in 2023. In eight years, when my boy will be applying to high school, will his recommendation carry any weight? I hope so, but it won't be the same as if he was the existing AD. I guess he'll have to get in based on good old fashion merit.

My window of opportunity for leveraging this relationship has closed. But that's OK, we had good memories of winning Northern California Sectionals twice.

Being A Writer With Fading Eyes

Around 2021, I noticed my eyes started to get really dry after only thirty minutes of looking at my laptop. They sometimes felt like they were bulging out of my eye sockets.

So I went to an optometrist who said I was staring at the screen too long and not blinking enough. One of my tear ducts was clogged and I needed to take breaks every 20 minutes by looking 20 feet away for two minutes. She then suggested I use preservative-free eye drops four times a day and use a hot compress to open up my tear ducts.

After 12 years of writing three-to-four times a week on Financial Samurai and publishing two books, I began to doubt my writing longevity. With my eyes getting so tired so quickly, my productivity will surely fade. As a result, I decided to record more podcasts.

If my eyes go, at least I can still use my voice. And if my voice also goes then hopefully my kids will be old enough and have an interest in continuing Financial Samurai.

For the past 14 years, I thought, “If you can speak forever, you can write forever.” Alas, my window of opportunity to be a writer may only last for 20 years. After 2029, at age 52, I suspect my productivity will go way down.

Having Children Is A Big One

Because I'm a man, I couldn't fully appreciate the concept of having a biological clock until we started trying for kids. After years of false hope I finally realized we should have had kids earlier.

No matter how much you want to believe having children after age 35, let alone 40, is easy, it isn't for the majority of couples. Your window of opportunity to find a suitable partner is really only about 17 years after you become an adult.

Even if you meet someone, you'll probably want to enjoy child-free living for at least two-or-three years after your union. Therefore, your window of opportunity to have children or stay child-free may be shorter than you think.

For those of you who want children and financial freedom, it's worth spending as much time finding a suitable partner as you do managing your finances. I've met many people who regret working so hard their first 15 years after college graduation because as older couples, they could no longer have children.

Fertility chart - best age to have a baby

The Perfect House For The Ideal Time

The perfect house might come along once every five years. But even if the perfect house is for sale, you might not be able to afford it. Even if you can afford it, you might still miss out due to a bidding war.

Let's say you successfully purchased your dream home. If it took 10 years of saving and investing after your last child was born, your window of opportunity to provide the nicest home possible for your youngest kid will only last eight years before they're off to college.

Ideally, you buy your dream home the year your first child is born. But the average age of a first-time homebuyer in America is about 36. This means the average 36-year-old is buying a starter home, not a dream home. In addition, if the mother is anywhere close to 36, then getting pregnant and staying pregnant may be more difficult.

This line from Death of A Salesman really hits home, “Work a lifetime to pay off a house. You finally own it, and there's nobody to live in it.” By the time some of us make enough money to own the perfect house, we may no longer have anybody else but ourselves to shelter.

Spending Time With Your Kids

For the average parent, 90% of the time they spend with their kids is over by the time the kids turn 19. As a result, it's best to spend as much time with them as possible while they're still living at home.

Go on every playdate. Teach them how to ride a bike and swim. Go to every soccer game and recital. Before we know it, our kids will be grown.

You may also think your window of opportunity to spend time with your kids is 18 years, but it is probably shorter. By the time your kids are around 12, they may prefer to spend time more time with their friends instead of you.

But if you've just bought your first home with a mortgage at 36 and have a lot more responsibility at work, it may be hard to find the time to spend with your kids. Juggling career and family well is mission impossible.

After a long day's work it can be difficult to muster up the enthusiasm and energy to play with your kids. All you may want to do is have a beer and veg out in front of the TV.

Who American spend time with by age

The Opportunity To Start Your Own Business

When I started Financial Samurai in July 2009, I woke up every morning at 5 am to write until 6:30 am. Then, after a 12-hour day, I'd come home, eat dinner, and often write and respond to comments from 9 pm until midnight.

Working 60 hours a week in banking while spending 25 hours a week on this site on the side for almost three years was untenable. As a result, I engineered my layoff with a severance package in 2012 to free up more time.

In retrospect, I'm glad I started Financial Samurai at age 32 because I still had plenty of energy. Ideally, I would have started at age 29, when I first came up with the idea. However, if I had had a full-time job and two young kids, Financial Samurai would have been unlikely to have ever been born.

Living in San Francisco, I've come across countless entrepreneurs who frequently work 70+ hours a week. Their work is all-consuming because the landscape is so competitive and the potential rewards are so high.

Once you hit 40, your desire to work long hours as an entrepreneur tends to drop off. You may begin to prefer working for Big Corp instead because it's easier to work for someone else than it is yourself. Once the clock hits 5 pm, you can mentally check out. Weekends once again become a time of rest.

Thoughts About Entrepreneurship From Jensen Huang, CEO of Nvidia

On the Acquired podcast, Huang responded as follows after being asked if he'd start a business again, “If we realized the pain and suffering and how vulnerable you’re going to feel, the challenges that you’re going to endure, the embarrassment and the shame and the list of all the things that go wrong,” he said, “nobody in their right mind would do it.” 

The Window To Get Rich

Getting rich requires luck, hard work, and longevity. Sometimes there are lost decades where your investments go nowhere or down, like from 2000 – 2011. If a bear market happens to wipe out 30% of your net worth over five years, you'll likely have to grind for many more years just to get back to even.

If you decide to go to graduate school, your window to get rich is even smaller. Knowing I couldn't last in investment banking beyond age 40 was one of the reasons why I got my MBA part-time. Those three years were beyond exhausting.

In a way, I believe the first million is the easiest because you have the most amount of energy and can take the most amount of risk when you're young. Once you have kids, a mortgage, and older parents to take care of, you have less energy and a lower risk tolerance.

Ideally, you want to get rich young enough so you can enjoy your riches. Getting rich after 65 is like getting a Ferrari after 65. Not as fun or impactful as getting a Ferrari by age 40.

In addition, your interest in getting rich as you age will likely decline because you realize there are more important things in life. After about age 40, you may finally begin to put your physical and mental health ahead of wealth and status.

Today, I no longer swing for the fences with concentrated single-stock investments. I mostly invest in private real estate funds, venture capital funds, and the S&P 500 index. Capital preservation and having appropriate risk exposure are key.

Buying The Dips

One of the reasons to be a long-term investor is that it's almost impossible to regularly time the market.

For example, there was a window of opportunity to buy the S&P 500 index on October 31, 2023, after a 10% correction from its July 28, 2023 high. However, that window closed in just one month and now the S&P 500 is much higher.

If you are still aggressively building your net worth, you should probably take advantage of stock market corrections and bear markets. Over time, the S&P 500 has proven to build wealth for investors.

S&P 500 stock market performance over various durations of time

Enjoying Old Age Can Be A Very Small Window

Nobody is guaranteed to live until the life expectancy of 73 for men and 79 for women according to the CDC. Your life could end abruptly at any time.

But here's another sad thought. Health can decline much faster in old age once you get sick. I used to play golf with one of my dad's friends every time I went back to Honolulu to visit. He was diagnosed with cancer one year and died within 12 months.

When we're younger, we feel like we're invincible. We can heal quickly like Wolverine. But when we're old, getting sick could be fatal.

The last thing you want to do is spend 40 years working at a career, retire, then die soon after. To hedge against not enjoying a wonderful retirement, live it up more today or retire early. You just never know when the end will be.

life expectancy for men and women in the U.S.

If you have debt and dependents please get an affordable term life insurance policy. My wife and I got matching 20-year term policies through Policygenius. We felt so much better after we did.

Compete For The Most Amount Of Time

One of the biggest mistakes we can make is thinking we have time. Don't be fooled. Life speed accelerates as we get older because every subsequent year is a greater percentage of the time we have remaining.

Hurry up and do the things you want to do, say the things you've always wanted to say, and spend more time with friends and loved ones before they go.

If you want to compete for anything, compete for the most amount of time to do what you want. Even billionaires don't live forever. But if you have more freedom than them, I dare say you are richer.

No Regrets

Looking back, I don't regret giving up my career and lots of money for having more freedom since 2012. More money wouldn't have made me happier because my job was making me miserable.

If you're thinking about taking things down, I say go for it! You can always go back to work after two or three years if things don't work out. Just don't forget to negotiate a severance if you do.

Now I'm cash poor after buying a house, so I'll have to find a way to earn again. At 46, however, my window of opportunity to get another full-time job is almost closed.

Will fortune shine again on this old man? I don't know but I will find out.

How to engineer your layoff - learn how to negotiate a severance package and be free

Reader Questions

What are some other examples where you have less time than you think? How do we counteract the loss of time?

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40 thoughts on “Your Window Of Opportunity Is Smaller Than You Think”

  1. Hey – been an avid reader for a long time. Sorry to hear about your eye and tear duct issues, have you considered lymphatic massages to clear the ducts and fascia manipulation around the neck areas to reduce eyeball strain? (i know it sounds crazy)

    I had similar issues and those improved my condition massively. If you ever come out to NYC let me know and I can connect you with a massage therapist that does work for professional athletes and actors. He doesn’t see retail any more except for referrals.

  2. Spending time with your spouse and expressing your appreciation in specific terms…which may initially sound strange. However for 2 people working full-time and if there is even 1 child, the window shrinks alot.
    People think that the person sitting, sleeping beside them knows how well they are appreciated. You must be explicit on what your spouse has done for you or how fantastic they look. Don’t just say how fantastic they look. Praise that colour on them, etc. I would suggest people look at Harriet Lerner, a well-know family therapist for some of her blog advice. She has published some books over the past few…decades.

    Window for travel can be narrow. Yes, it costs money and now with some more severe climate /weather conditions, rethink this and don’t it off in 10 yrs. Everyone knows all the hiking, walking up and down ancient hundreds of steps..requires good health and fitness. We did alot of multi-day day, multi-wk. bike touring trips with our own gear/clothing.

  3. Sam – a very sobering blog post! But to suggest you’re somehow washed up at age 46 is nuts.

    I’m 23 years older than you (age 69), and I feel that an exciting new phase of my work life (as a tech transactions lawyer) is just beginning with the advent of AI tools. I’m still pumping iron and doing high-intensity classes on my Peloton. Next month I’ll join my youngest brother, my daughter and my daughter’s boyfriend in Cancun to learn wing foiling. Maybe later it will be a surfing or a spear fishing trip. I’m still traveling a lot – mostly for fun – and haven’t flown economy in ages.

    I admire the vulnerability you share on your blog. But if your self-image becomes one of a man with fading eyesight, fading strength and limited opportunities, that self-image may become reality.

    Obviously windows of opportunity do close. I’ll never step into the MMA ring with Sean O’Malley or go on a concert tour like Taylor Swift. But plenty of opportunities remain, regardless of age.

    1. Thanks. I’m just trying to be realistic about the future.

      Consider yourself lucky to learn wing foiling at 69! Please take care and try to avoid injury.

      Enjoy your new work life as a tech transactions lawyer.

  4. A thought provoking post, but also a very depressing post. Life really is fleeting isn’t it. In the blink-of-and-eye we will all be dead. And to think that 1 or 2 hundred years ago, life was significantly shorter than even today. Had I lived 200 years ago, I probably would be gone by now (I am 58). I find it kind of depressing that at my age, while active and healthy (for my age), you know already you are in decline (reading glasses are required, your physical (and should I add, sexual) energy it not what it was). Lets face it – the window of opportunity for every item mentioned in your article is closed by age 58. Either you have done it, and can look back on it, or you can regret if you have not done it. By the time you get to your late 50’s all you really have to look forward to is 20 to 40 years (if you are lucky) of continual decline with your ability to acomplish and achieve diminishing year by year.

    Oh well ! Enough of this depressing talk. It is the reality – We just need to remember that the most valuable asset anyone ever has is TIME.

    Happy Christmas and New Year!

    1. Is 58 it? If so, man, I got 12 years to really make the most of life! But I feel I’ve tried almost everything I’ve wanted to do in my life so far. So I feel content.

      Happy New Year!

  5. Another great article. I started a business this year and within a few months it did better than expected. At the same time we have two young kids, are FI, and I already have a part-time job where I work about 9 to 13 hours/wk (which covers all our expenses). I love the business minus the networking, marketing, and time suck thinking about how to grow it. I’ve learned I don’t actually want to work a lot, nor do I want something to occupy my time to the point that it impacts me from being fully present. So I stepped off the pedal and will gradually let it go as clients graduate. 10 years ago would’ve been a good time to start, but right now, time is way more precious and there are many things to enjoy that don’t involve making money. This is the opportunity you get from financial independence (courtesy of real estate).

    Btw-just gave you a review on Amazon for your book. Your content is much appreciated!

    1. Thank you for the read and the review. I really appreciate it! Every review makes a difference.

      Working part time while financial independence is a great combination. With kids taking up so much energy, I think about 20 hours a week of work is ideal. Until they go to school full-time.

  6. I don’t know, Sam.

    Yes, life is harder than what we thought life was going to be like when we were kids but window of opportunity is not as smaller as we think. A year is an *insane* amount of time to pass. Many think “life is short”. Nope, life is long. People need to stop lamenting that life is too short.

    For example, your window of opportunity to play USTA at 5.0 lasted 13 years. Playing tennis for *over* a decade is an insane amount of time.

    Life is hard but it’s not bad.

    1. Windows are partly short, because it takes time to recognize an opportunity, and then take action.

      I didn’t really have 13 years to play at the 5.0 level because I had to train and get better over five years to get to that level first. And then Covid stopped the season for one and a half years. So this demonstrates unexpected variables can take away opportunity.

      The older we get, the more I think we will recognize time is short. There’s a reason why there’s the saying, “time is wasted on the young.”

  7. As the country song goes, you can always do it.. till you can’t. – Cody Johnson

    You can tell your old man
    You’ll do some largemouth fishing another time
    You just got too much on your plate to bait and cast a line
    You can always put a rain check in his hand
    ‘Til you can’t
    You can keep putting off forever with that girl who’s heart you hold
    Swearing that you’ll ask some day further down the road
    You can always put a diamond on her hand
    ‘Til you can’t
    If you got a chance, take it, take it while you got a chance
    If you got a dream, chase it, ’cause a dream won’t chase you back
    If you’re gonna love somebody
    Hold ’em as long and as strong and as close as you can
    ‘Til you can’t

  8. James Winston

    18-35 is the window to join the military, and 18-28 is really preferred.
    I served in the Marine Corps for 6 years. Glad I made the choice when I did.

  9. Buddhist Slacker

    You have less time than you think to fly out to see one of your elderly loved ones when they start the process of dying. I thought I had so much experience estimating how much time I had to get there but you never know. I delayed leaving too long and my mother-in-law died before I got there. Please don’t make the mistake I did and regret it for the rest of your life.

    I have so much less time than I think to get all the things I need to get done in a day. Minutes turn into hours and fly by. But somehow, the years until my retirement date drag on and on and on.

    Samurai, you’re nowhere near an old man. I’m 61 and I’m just getting started on the next best two decades of my life. Recoup your perceived lost time by pivoting into something new which at the same time leverages your existing skills for the next 20 ears of your life. Then do it again for the 20 after that. There are more steath 90 year olds walking around than you realize. Talk to some of them and ask them how old they are. We just notice the unfortunate people who have limited mobility at 70 or 80. Working is the best way to stay young.

    1. Sorry to hear about your MIL. Thanks for the reminder.

      I’ve felt like an old soul since 13. 33 years later, nothing has changed.

      The good thing is that the older I feel, the more I want to live to the max in the present.

  10. Frugal Pharmacist

    Less time with our aging parents. Taking both mum and MIL on a big overseas trip this year before they hit an age where long distance travel will become too difficult.

  11. Jonathan Johnson

    Good article. As you get older (63 here) and have achieved your financial goals, your focus goes from wealth to health. I found using the same discipline/energy that helped one achieve financial goals can now be directed toward maintaining a healthy lifestyle. It’s nice not having to think about money all the time.

  12. Charles Dart

    Thoughts About Entrepreneurship From Jensen Huang, CEO of Nvidia

    On the Acquired podcast, Huang responded as follows after being asked if he’d start a business again, “If we realized the pain and suffering and how vulnerable you’re going to feel, the challenges that you’re going to endure, the embarrassment and the shame and the list of all the things that go wrong,” he said, “nobody in their right mind would do it.”

    Sorry, but this is bullsh*t. Successful entrepreneurs who say this say it to lionize their own achievement. Huang would do it again and again, no regrets. Being an entrepreneur and making it (which he did) is one of the super highs in life.

    Financial Samurai wasn’t easy to make a success, but I bet you’d do it again in a heartbeat.

      1. Charles Dart

        Fair enough.

        But all things being equal (i.e. same circumstances) would you choose to start again, or nah just too hard and crazy better stay corporate like Huang says? lol

        I can answer for myself.

        Starting, building and selling my business was the most challenging and rewarding thing I’ve ever done. It drew on all my ability. In the early years it was all cost, zero income. I wondered “Am I wasting my time? Is this ever gonna work?”

        There were plenty of days I thought about quitting, but instead just kept going. Those days got fewer and further between over time as I improved and the biz grew.

        The whole thing A-Z was one of the most gratifying achievements of my life, just behind my wife and 4 kids.

        And yeah, I’d choose to do it again in a heartbeat if could go back in time. It was an awesome ride.

        That’s why I just don’t buy it when a successful entrepreneur says something like this. It’s a humblebrag.

        1. Yes, I’d start this site again when I did. Without kids, it’s much easier.

          If you were to ask me now, I would probably say no. Too much work and criticism without enough reward. Think about it. Have you ever paid anything to read or listen to FS? Have you ever purchased Buy This Not That or How To Engineer Your Layoff and left a review on Amazon and Apple?

          For the majority, the answer is no. And it can get disheartening when a reader can’t even leave a review despite providing value for so many years.

          Writing is a labor of love. You have to have the intrinsic motivation to keep going as a writer. Otherwise, it’s almost impossible to continue long term.

          How much did you sell your business for? And if you enjoyed it so much, why did you sell?


          1. Charles Dart

            I’ve dabbled in the blogging business, so feel your pain. Dealing with the public can be frustrating. A lot of complainers and takers out there. But also gratifying to add value to people. Challenging to monetize at scale though.

            People don’t value what they get for free. Learned this the hard way in my business. When started I would give prospects valuable free advice which they happily expropriated, then not buy. Oddly, when I stopped giving free advice (“Happy to share after we receive payment!” lol) our close rates went up. Lesson there on sales and human nature (in sales you learn about people real quick).

            We sold the biz for mid 7 figures. A couple reasons: 1) I enjoyed building it, but it was getting repetitive and I couldn’t see doing it forever, 2) Hiring a professional manager and stepping away wasn’t an option, 3) Best time to sell is during that hockey stick growth – the window closes if growth flattens, 4) Gave our family some options/flexibility we wanted, 5) Nice to take a “win” and do something different.

            Thank goodness we sold, because then covid hit and on top of that competition is more brutal than ever. The buyer is having a rough time (I think he’s screwing it up, but all entrepreneurs think about buyers that way lol).

            We are getting bored now, would like to start something new or even buy a business. But to your point, with young children it’s a whole different ballgame. It would be much harder to start our old biz with several kids.

            I did buy your book btw. Thanks for writing it.

            Have you ever considered a paywall for some of your content? Buy a bundle subscription, get “Buy This…” plus access to an exclusive forum or something. I’ve never done it so don’t know how well it would work. But my wife was doing a niche professional blog and we brainstormed how to monetize it after she got some traction. Our conclusion was the model was too thin, at least for her niche.

            That Financial Samurai has done so well is a testament to your unique voice, valuable content and great SEO-sense. Well done!

            1. Thanks for picking up BTNT. A review on Amazon is appreciated!

              Regarding monetization, the irony is, the more I focus on monetization, the less I want to do anything. So the less I focus on monetization, the more joy I have, which also leads to monetization.

              Can you talk about the tax liability from selling a business? I’ve thought about selling in the past, but lopping off 40% for taxes sounded too painful.

              Either way congrats on your sale!

              Related post: why I regret selling my online business for millions

  13. Re: fading eyes — Have you tried using a dark theme online? When I had cataracts, my eyes quickly got tired when reading. The glare of the white background was the problem. Then I began using a dark theme online wherever possible, and suddenly reading was easy again. (Physical books with white pages, of course, were still a problem.) I had not yet retired, so I managed by doing as much of my work as possible on the computer or tablet or phone, all with a dark theme.

  14. Daniel Cohen

    Hey Sam,

    Thank you for writing this article. It has a lot of good points. I would like to challenge your assertion that “Life speed accelerates as we get older because we have less time remaining.” Wouldn’t it be more accurate to say that Life speed accelerates as we get older because 1 year when you are young is a big part of your life time versus when you are old, it is now a lot smaller? E.g one year for a ten year old is 1/10th of their life while 1 year for a 50 year old is 1/50th of their life.

  15. Yes it is so true that life accelerates as we age. I definitely feel it more and more each year. Although there are countless things I wish I had done or done better when I was younger and had more energy, I try not to look back on life with regret. Each night I stay awake writing, working, or doing something productive that I enjoy or need to do until I literally can’t keep my eyes open anymore. So even though I’ve slowed down since my 20s and 30s, I’m doing the best I can with what I have in the moment.

    “Tomorrow is a mystery. Today is a gift. That’s why we call it ‘The Present’.”

  16. I had problems with my eyes since my engineering days. At the end of the day, I couldn’t read the text on the monitor anymore. It was dry eyes and fatigue. That’s one of the reasons why I quit my engineering career. I spent way too much time staring at the screen. These days, I don’t spend as much time on the computer, but I still have problems after a few hours. It might be time to retire for real.

    1. I hear you. Old ages doesn’t do our eyes any good. Our cones die and we just have more trouble seeing. Someone people lose their eyesight quicker than others.

      The pandemic propelled me to spend too much time on the computer, accelerating my eyesight’s decline. Darn.

  17. Great article. Great reminder.

    You, or rather Mr. Lowman, bring up an interesting point. I’ve always wondered if home ownership would be more attainable today if the 30-year mortgage never existed. Thoughts?

    1. Financial Samurai

      I think the 30-year mortgage made homeownership way more attainable than if everybody had to pay 100% cash. No doubt. In some cases, there are even longer mortgages now… 50 years!

      1. I think it did make it more attainable for a while, but now that it’s normal, we’re back to low attainability for the average person. Mortgages keep getting longer to keep the payment down. If the mortgage never existed, home prices would be much lower than they are today.

  18. Charleston.C

    Sam, really appreciate these life insights. I find these reflection type of posts as impactful (if not more) as the data driven financial type of posts, as it places the financial topics in context with our lives.

    Keep up the good work!

    1. Financial Samurai

      Thanks for taking the time to read and comment. End of the year is the time for reflection. And I have a lot of things on my mind.

      1. Hello,
        Just wanted to say thank you for your blog. I have enjoyed reading it for many years and have learned a great deal from it. It never occurred to me that you wished to hear from your readers until I read this post today. Thanks to financial blogs like yours, at 65 I am able to have a secure and relaxed retirement. I work (as a physician) 2 to 3 half days a week because I love my work and can’t yet bring myself to give it up entirely, but we’ll see how long that will last.
        Thanks again for teaching me about financial well-being.

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