Celebrate Small Wins To Keep Financial Motivation Alive

Life is like a bucket of cherries. Don't each one go to waste!Building wealth is a long game. It's sometimes very easy to get discouraged as a result. Despite a lucky investment when I was 22, I felt very little pleasure having a large savings account in my early 20s. Money degenerates to just numbers on a screen that provides no utility unless spent.

I was actually considering quitting my newfound job in San Francisco after two years in 2003 to live a vagabond lifestyle in Hawaii. Surf in the morning, massages in the afternoon, and Mai Tais in the evening can't be that bad. Thoughts of buying a Eurovan VW to go road-tripping across the continent as I took showers at rest stops also crossed my mind.

It's dangerous to receive a financial windfall so early in life because there's a risk of saying fuck all to everything. You suddenly think building a sizable financial nut is so easy, when it's clearly difficult in a short period of time. With a sudden injection of wealth, you may never achieve your potential because you simply don't bother trying as hard.

After much deliberation and a perpetually drunk upstairs neighbor, I decided to buy my own property to “get rid” of my money. I was sick of renting and I was also unmotivated to work for money, a big problem if you work in finance! As soon as I plunked down the six figure check I felt a sense of relief. Having no money never felt so good!

Finally, I'm working for something more, I remember thinking after paying my first mortgage payment. Living in a nicer property instead of a dingy one bedroom was a reward for four years of hard work and risk taking. Slacking off was not an option because if I did I might lose my home!

Perhaps the real reason why I love property so much is not so much for the returns, but for the refocus it provides. Mortgage debt saved me from being another know-it-all kid who throws his life away at the age of 26 due to a lack of patience and perspective. A mortgage was the anchor that kept me from blowing away.

Years later at the age of 32 my enthusiasm for work once again began to fade. 10 years raced by after college but I was afraid to go out on my own because work was all I knew. The Dark Side Of Early Retirement was penned to make sure I wasn't falling into the same trap without any purpose. When the post was published, I was immediately bashed over the head by the early retirement community if you read the comments. Little did they know my goal was to purposefully bash my own crazy thoughts to make sure I wasn't missing anything before deciding to take the leap of faith two years later!


Although I only made $1,400 from my Apple structured note, I could very well have lost $10,000 if Apple closed below $415 on the June 17 strike date. The stock is currently trading below $400 at the time of writing this post. Is avoiding a loss a win? I think so! With the small Apple win, I've decided to spend a good portion of the $10,000 I might have lost on seeing the world again.

Travel is in my DNA. When you grow up living in six different countries before your 14th birthday it's impossible not to want to continue seeing what's out there. There's nothing better than picking up local customs and learning new languages even though I'm pretty horrible at linguistics. It's the idea of pretending to be someone else in a different land that excites me most.

Each year since college I've gone on some international adventure. Last year was Amsterdam, Helsinki, Copenhagen, Brugge, and St. Petersburg to understand the happiest people on earth. The year before that was Rome, Barcelona, Malta, Santorini, Olympia, and Istanbul. This year I'm visiting Mallorca, Spain to understand how to find happiness within a country that has a 20%+ unemployment rate. Along the way I'll spend a week in Switzerland to learn about their neutrality. On the way back, I'll stopover in Frankfurt for a day to experience German precision, beer, and bratwurst of course.

There is a part of me that believes the US is slowly turning into Europe due to the growing size of our government. Structural unemployment will stay stubbornly high, tax rates will go up for everyone, and there will be less innovation as Americans learn to kick back more and live the good life. When was the last time something big came out of Europe or Canada? Exactly.

I've seen the future of America through my experiences in Europe, and I've got to admit the future looks fine. If you don't have to worry about egregious health care costs you'll be more adventurous. If you've got a huge government safety net that will provide you 70% of your last year's pay for a couple years no matter how much you make, you'll never need to engineer your layoff to protect your deferred compensation. We'll all be one big happy family that's full of socioeconomic equality.

Before your criticize me for my optimism, I encourage you to spend at least a month in Europe and see for yourself. I'm a realist who accepts things for the way they are. Who doesn't like chocolate, cheese, beer, red clay courts, bikini clad beaches, and a tradition of afternoon siestas? The European lifestyle is wonderful.


There's really no point making money if you don't spend it on things you love. The key is to figure out how much you can afford in order not to come up short. Enter my savings guide by age to help keep you on track. Identify purposes for why you are saving money. Examples can include travel, a child's education, a dream property, a charity, or an around the world cruise for your parents. Financial freedom as a reason might not be specific enough.

Everyone has to find their own balance. There is a risk you just might accumulate more money than you ever thought possible at a young age and pull the rip chord too early. By the time you realize it would have been better to balance out your spending and savings habits instead of going to either extremes it might be too late!

Financial Samurai Motivation Category

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Photo: Life is like a bucket of cherries. Eat too many and you'll be sitting on the throne for a very long time. Brentwood, CA, 2018.

47 thoughts on “Celebrate Small Wins To Keep Financial Motivation Alive”

  1. thepotatohead

    Right now I’m focusing on paying off my debt and building up my emergency savings and keeping adding each month to the retirement funds. I think once I pay off the bulk of my car and personal loan debt, and then max out my 401k and IRA I’ll start going back into a better balance with spending and saving. It’s definitely really heavily on the savings side now.

  2. oops TYPO I meant “sending them” not “ending them”–yikes I don’t want him to “end” them!

  3. Alvaro L. Hardy

    Trust this advice… I worked for SSA for over 15 years and have had to reconcile my own earnings records. You just HAVE TO keep these records unless you are willing to be a victim of record keeping errors or the failure of long-past employers who failed to report your earnings to SSA. This is especially true for the early years where we may have held multiple jobs and jobs where the income swings widely as in sales or construction, etc. Earnings in the early years have the greatest multiple in computing benefits as they have been with Social Security for a longer time. After further discussion with my girlfriend, a retired Claims Authorizer at SSA, I/we also suggest that if one is dissolving a marriage of 10 or more years each partner should have the earnings records of the other partner and be granted future access as part of the divorce settlement.

  4. I have been feeling burnt out on frugality lately too.
    I’ve already got a house with a mortgage I need to pay, but it may be too small of a mortgage.(mortgage+tax+insurance is only 9% of gross household income between Mr Geek and myself…)

    Maybe I need a 2nd to rent out?

    I bought some new clothes and am now on vacation. This is helping.

  5. The Phroogal Jason

    I too love to travel and have been to over 30 countries. 20 countries alone in 2012. It’s in my DNA. I also believe its important to enjoy your money when you can enjoy your money. It doesn’t mean willfully spending it away but using it for those planned things that bring joy in life.

    I celebrate wins all the time and its part of my strategy on financial independence.

  6. It’s very necessary to reward oneself for any accomplishments, big or small, because it is greatly motivating. You do not need to spend lot of money on those rewards, but make it a point to get the thing you really need and want, and not to buy things on impulse just because you have the means to do so.

  7. I do think you are right about celebrating the little wins, but I think it is just as important to plan for the big ones. It is easy to get caught up in the little stuff, but every time I’ve implemented the 80/20 rule to focus on the big stuff, I’ve been happy I did.

      1. The Phroogal Jason

        I agree. Life is meant to be lived. Happiness is shaking things up once in awhile.

  8. It’s a strange connection I have here, but this quote from you, “There’s really no point making money if you don’t spend it on things you love” reminds me of general work-life balance. There’s no point in having a high-paying, pie-in-the-sky job if you can’t also be at home at night with your family/friends. There’s always a balance. Making too much money can be rough, actually, as can makign too little. Same goes for working too much or too little. It’s all a balancing act!

  9. I was in Palma de Mallorca about this time last year. Unfortunately, it was with the US Navy, but it was still fun none the less. There’s a double decker city bus tour for like 15 Euros which is worth it as you can ride it all day long for transportation after the tour. On this tour is a pretty cool castle. The food is great. Beer isn’t bad. Of course the wine is good. And if you’re into the beach party scene there’s plenty of it down at Magaluf. There were plenty of vacationers (or people on ‘holiday’) there. Good stuff; I’d love to go back!

  10. I like having small celebrations like dinners out or picking something up at a bakery. Can you tell I like food? :) I’d much rather have many small celebrations than fewer large celebrations.

  11. Sam, I can’t believe you don’t like one of the main ingredients of an enjoyable diet. Well mine at least. :-)

    Another great article to be sure!

        1. OK, but I don’t think I wrote anywhere that I don’t like chocolate! “Who doesn’t like chocolate, cheese, beer, red clay courts, bikini clad beaches, and a tradition of afternoon siestas? The European lifestyle is wonderful.”

        2. That’s crazy … I read that with a comm just before the “Who” for some reason.
          Which would have read “I’m a realist who accepts things for the way they are, who doesn’t like chocolate, cheese, beer …”
          Great info as always Sam!

    1. Funny I think the opposite is true for me. I recently described my mortgage to friends as an anchor because I just had to turn down a second job transfer offer. Without some type of significant loss its hard to get out from under this weight. Maybe my career would take off and this loss would be insignificant (compared to the gains of an accelerated career in the other locations). very hard decision..

      1. There really might be something else that is bothering you, or that you could work on to improve your career rather than your mortgage. But, you can always go for that golden opportunity and rent out your house no?

      2. Something else? Im happy in my current career, but its been my experience those that transfer , long term, turns out to be more satisfying and lucrative for them. Turning down these offers is almost like saying “no thank you” to higher job satisfaction and networth 5, 10 years from now. Renting out, Ive investigated. Im very risk adverse and prefer to put the property and mortgage in a LLC, but my mortgage co wont let me unless the LLC can show income. Also, due to condo fees I would bleed about 3k/yr even if I found an ideal renter (12 months paid on time, etc). Buying this thing has been a drag.. makes options limiting..

  12. And I think it’s fine other countries aren’t making headlines about creating the next great product or company. America is filling these shoes now, and maybe in 20 years China will so the same as we fade into a more socialistic environment.

    All is good and rational.

  13. I’ve never really thought about a mortgage as an anchor
    It always seemed like a prison to me because it restricts my ability to get up and move quickly. But maybe that’s just what I need sometime in the next 5-10few yrs.

    1. It certainly does have restrictions, hence one better be fairly certain they want to live in the location of purchase for the next five years.

      I’m pretty sure I would have been a vagabond after age 25 for a couple years if I didn’t have my home which is now a rental. It’s easy to say you’d rather be free in your 20s until you realize nobody is going to save us except for ourselves.

  14. Great Article Sam – spot-on for those of us trying to keep the light at the end of the tunnel in view.

    1. If I bought the $20,000 Eurovan, I wouldn’t have bought my first property. If I didn’t buy my first property, I would be able to earn it’s current income which allows me not to work. Hence I have to so I’m glad I didn’t do it! I came to my senses and realized I have years to do a cross country trip.

      Besides, I can’t stand driving for more than three hours at a time!

  15. We are just about to have a huge celebration in my family. My wife is finishing up her requirements to get her CPA license. It has been a long two years of studying, studying and more studying. We’ve already planned a big night out on the town with the entire family to celebrate all of the sacrifices we have made these past two years. Celebrate success…absolutely!

  16. Sam,

    I’m reading this post from an apartment villa balcony that’s overlooking the courtside pool in Punta Cana, Dominican Republic. I don’t celebrate wins. I stay on the same course. Stock away as much money as I can and then when I want to take a trip somewhere, when my career allows the time off, do something I want without feeling guilty about it.

    Enjoy your trip to Europe. I never ventured out of Italy when I lived there so I can’t help you with tips. May I suggest Tripadvisor? Sightseeing is not my thing. I go abroad to experience as taste of what post-retirement would be if I decided to become an ex-pat in the country that I’m visiting. Be sure to hit me up if you ever find yourself in Punta Cana.

    1. I do the same and pretend how life would be like as an expat as well. It’s very fun to try and act like one already lives in the host country.

      With a government pension, is kick back at 40 in DR as well!

  17. The First Million is the Hardest

    I’ve always made it a habit to reward myself for the “wins” in my life. Letting myself buy something I’ve always wanted but wasn’t necessarily “in the budget” makes those occasions (graduating college, getting a new job/promotion…) seem like they were worth working for & keeps me focused on the next goal down the road.

    1. I don’t actually. I always knew that I could take that trip some other time as the continent wasn’t going away. If I bought the Eurovan, I wouldn’t have bought my condo. No condo would put a crimp to my early retirement plans as it brings in some good cashflow.

      I decided to take as much vacation as I could my last years and enjoyed it tremendously.

  18. I usually reward myself for accomplishing almost any accomplishment. The reward may be small, but it motivates me to accomplish it. For example, If I check off all the things on my list, I might go to Starbucks. I usually go once a month anyway, but I attach it to the accomplishment. I think it is a for m of a game!

  19. Another timely post! Boy, do you have your finger on the pulse of your readers!

    I was actually about to ask you today about how to avoid frugality burn-out because, over the weekend, I was really feeling just burnt out from saving. Yes, I am on target to save 50% my annual of my takehome pay now (and I support two kids and a stay-at-home-father and I am a female) so yes I pat myself on the back for that enough…but golly…I haven’t been able yet to pull the trigger on some investments I’ve had my eye on because of how dicey everything is right now…so I haven’t really had investments lately to distract me…other than the money “earned” on things/investments I got myself to not buy. So, like you say, the money saved right now is looking more like just numbers on a screen…

    As I waited my turn to get my morning coffee this morning I told my co-worker ” I’m just not feelin’ it today. Maybe I will after my morning coffee.”

    But it wasn’t the danged coffee. Inside I just felt burnt out from working my butt off and having the tax man take half (I’m in CA) and then I sock away half of that to savings and then keep doing that day in day out for numbers on a screen. Here I am at my desk and your article is the first thing of the day I am reading…and gosh I can soooo relate to you on giving it all up to just live a “simpler” lifestyle. I have a family to take care of so vagabond life is not an option, but there have been times when my husband and I have talked about me leaving my company to take on very simple, low paying venture with no pressure to produce, maybe something in admin or ops or a non-profit, or even just start a homestead and become farmers in a more beautiful, happier, more tax advantaged state/country with our savings to bridge the gap. We went so far as to start planning where, when, how, budgets…but I would eventually would snap out of it when I would realize that the problems/feelings I have at a high paying job would be the same at a low paying venture no matter how nice the scenery…a-hole bosses and vendors, office politics, corporate maneuvering co-workers, quotas, boredom, burn-out…and there is ALWAYS going to be someone pressuring you to produce whether its yourself or someone else…the whole 9 is there at $30K/year as much as it is at $250K/year…so if I’m going to have to deal with that anyway, might as well deal with it for more money than less. Anyway, I digress, but my point is the idyllic fantasy of “simpler” life can be just as problematic and not the answer to ones problems, as much as in our fantasies we would like them to be…so I keep plugging away…

    I guess that answer is that I need to start planning a vacation like you!!!!!!!!!! I’m going to do it. I need it.

    I’m SO happy you are going to spend a week in Switzerland! I have always wanted to go and have heard so many good things. Beautiful country with beautiful people. My husband and I have always been very interested in physics (hobbyists if you will?) so the Large Hadron Collider is a must see for us. Exactly what dates will you be out there? Check to see which festivals will be going on make plans to attend the ones that interest you. Oh and you are going to Lucerne! Of course I don’t need to tell you to go hiking while you’re out there…ugh…I’m so jelly!!! I hadn’t planned to go until my kids were old enough to handle such a long flight so it will be a few years yet until I can go…

    1. Hi K,

      Yeah, whether you make 30k or 250k the frustrations of work are pretty similar. So you might as well make 250k!

      What about cracking the whip on the hubby to find a part-time or full-time job as the kids get older? That would boost savings or alleviate your work stress.

      Thanks for the tips for Switzerland!

      Yes, sounds like it’s vacay time for you!


      1. Hi Sam!

        Actually there is no “whip cracking” on the hubby that needs to be done, him being a SAHF was a very well thought-out decision that turned out to be one of the best decisions we ever made. It’s funny because there is always this stigma associated with being a SAHF–this assumption that he lost a job or couldn’t get a job or that he is a “Tyrone” (from Erykah Badu’s song). I know that’s not what you were not suggesting, but “cracking the whip” is usually intended for people who need to be motivated, ie, lazy people, so maybe it was just the wrong choice of words?

        The truth is that when we got married we agreed that one of us would stay home with the kids and would homeschool them, and that who would be the one to stay home would be decided by what would make the most financial sense. When our first child was born, he was making $30K and I was making $100K. We looked at our career trajectories and income projections and it was clear that it would make the most financial sense for him take on the responsibility. We also looked at childcare costs and private school costs at the time and in the long-run for multiple children, and concluded that childcare/private school would end up costing MORE than what he makes/will make AND would be lower quality and more risky/unsafe than the care and education that he/we can provide.

        Just a few years and two kids since we made that decision, I am now at the $250K/year level and am able to provide us with a comfortable life. Yes, it is stressful for me, but him working and not being a SAHF would not alleviate the stress. Quite the opposite, part of the reason why I am able to work this hard, focus, and produce the way I do is because I don’t have to worry about anything else. And he really is amazing in his role. He’s a brilliant educator, both kids are gifted and very advanced for the ages, they are extremely healthy, very athletic, and so well behaved–and I rest assured that they are always protected by him. You can’t put a price on what he does, but if you had to, it would be a VERY HIGH price tag because he is their body guard, private tutor, athletics coach, personal chef, driver, and parent, all rolled into one. I’m really not just bragging (if I were, why not, he deserves the praise and spouses SHOULD praise their spouses!), but he takes his role seriously and IMHO does it much better than any private security, tutor, private, school, coach, or chauffeur I could ever hire–and beyond that, I can TRUST him with them–I can’t fully trust a team-for-hire that they won’t hurt them–let’s be frank here, things like that are in the news everyday and everywhere and is every parents worst fear.

        By the time the kids are old enough for him to start looking at a PT for FT gig, he will have succeeded in his role which is ending them to a Tier 1 college and it will be empty nest time–and I’m hoping that’s when I will have saved us enough money to start having some fun!!! If not, then I failed in my role as provider. So that’s why I need to stay on sites like this and have conversations like we are having now in order to stay on track!

        Anyway, I hope you have an AMAZING time in Switzerland (and Madrid/Mallorca/Frankfurt for that matter!) I’m looking into vacations–but in the meantime my temporary stress reliever is locking my office door so that the people out there can’t bother me LOL! Thank goodness I’m not in a cubical. My head might have exploded already!!!

        Cheers and thanks again for all of your insightful posts/articles!!!!!!


  20. I agree it is critical to have that balance of saving and spending…for so long I was a tightwad saving nearly every nickel. I’m sort of glad I did have a skill for delayed gratification as it has allowed me to be in a good position, but now it is all about work/life balance. I’ve got a nice investment distribution payday coming this week that in lieu of buying something material like another watch or car I’ve committed to spending a nice chunk of it on travel…I’m thinking Costa Rica or Thailand, or both!

    1. Let me know if you go to CR. I was going to go for 10 days and nixed it because it is hard to get to. Thailand would be great! But unfortunately also a pain to get to from SF.

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