To Endless Perfect Summers

This post is an ode to endless perfect summers. For finding our ikigai and doing things we care about the most. The pandemic has really made me and hopefully you realize that time is precious. We most focus on doing things that are meaningful and that matter!

Imagine standing barefoot on the sand just far away enough so the water doesn't kiss your toes. A flood of orange consumes your eyes as the sun sets over the hills. You give thanks for the moment and hope tomorrow will be just as wonderful. Such is one day in a perfect summer.

Perfect summer sunrise, Monterrey, California

From 1996-1999, I experienced three perfect summers. They were filled with adventure, passion, heart break and learning. I was 19-22 at the time and couldn't be more excited to experience the world. The lack of money didn't matter. What mattered was the thrill of the unknown.

When The Good Times Ended

My first summer after a year of work in 2000 became a non event. Despite having more money than ever before, I wasn't able to spend it. Taking more than a week off a year was frowned upon for first and second year Wall St analysts.

The good times as I knew them had ended.

For the next 10 years I longed to replicate those carefree, wonderful times. But when you're doing everything you can to get promoted and make money, it's very difficult to cut away.

I came close in 2011 and 2012 when I took six weeks off to travel, but it still was not the same since the most I could leave would be for two weeks at a time.

I Finally Found A Perfect Summer Again

After spending four weeks in NYC, Switzerland, Mallorca, and Germany as well as another 12 days back in NYC for the US Open, I've finally rediscovered the magic of a perfect summer.

I waited a full year to take a big trip after leaving Corporate America in 2012 due to uncertainty. With the elimination of W2 income I was intensely focused on building my online business.

It was over the next 12 months where I had to really see whether there was truly correlation with effort and reward. I'm glad to say such correlation exists.

As an entrepreneur, I felt like I was once again a first year analyst who had to prove myself to my boss, who so happens to be me all over again. My expectations are always set very high – most notably a goal to generate $200,000 a year in passive to semi-passive income within three years of going solo.

The Green Light

So what happened in the past twelve months that flicked on the green light to escape from San Francisco for six weeks in one season? How did I let go and get out to rediscover a perfect summer? I accomplished several things actually.

1) I finished writing my book on how to negotiate a separation package. The book was a bucket list item for me. Fortunately, it's been successful and was recently updated and expanded. Be sure to check it out.

2) I gave everything I got to producing meaty content here and elsewhere. I'm not sure if I could have sustainably tried much harder to write content.

3) I launched the FS Forum.

4) I surveyed all of you to figure out how this site can improve, and

5) I set the wheels in motion to build a scaleable advertisement network through Yakezie.

The hardest part about building a business is the launch. Just thinking about starting a new project makes me never want to start one! More work begets more work to the point where I often wonder what have I gotten myself into.

Make Sure Your Finances Are On Track If You Want A Perfect Summer

Figuring out how to effectively generate recurring revenue online is no joking matter. The online world is competitive and fraught with exogenous risks way outside your control.

For the blog, my hope is to continue having readers constantly be surprised to find out I generate a viable income stream. For the business, my goal is to make the Yakezie Network the number one personal finance network where high quality clients would like to advertise.

If I fail to achieve my revenue targets after two or three years I would probably go back to work because I frankly don't want to just live off ~$100,000 a year in passive income.

I could draw down from the nut if I needed more, but the ideal retirement withdrawal rate touches no principal. It's no fun to cheat on your finances.

Timing Is Everything For Perfect Summers

Living off $100,000 a year in an expensive city like San Francisco is not a luxury if you have to start supporting a family.

And no, I'm not willing to live in the middle of nowhere just to cut costs. It obviously can be done, but I don't want to settle since I know I have the ability and energy to generate more.

If the time comes for starting a family I don't want a silly thing like money to get in the way of harmony.

Thankfully, the hard work between June 2012 and July 2013 paid off. Google algorithmic land mines were avoided, traffic reset higher, and targets are on track. With the one year milestone out of the way, it was game on to explore!

What Makes A Perfect Summer?


New people can be strictly platonic friendships or unexpected passionate romances like in Eat, Pray, Love. I met a new friend who can literally sit and watch tennis with me for eight hours a day for days on end.

That's amazing because everybody thinks I'm crazy for being such a tennis nut, but not this one. Special people complete any perfect destination as we inherently want to share our experiences with others.

New Destinations

Every perfect summer seems to have a new destination because of the adventure of exploring the unknown. My favorite destinations of the past are Taipei, Beijing, Shanghai, Tokyo, Amsterdam and Mallorca. It's thrilling to be constantly surprised by what's around the corner.

A Long Enough Duration

Once we start work, most of us never get to experience two-month long summer vacations again until retirement. Those who work in education are lucky that way. I used to think I'd get a little homesick after two weeks.

That is until I took a four weeker this summer. Now two weeks seems like a breeze and there's no need to buy a vacation property in every desirable vacation spot to avoid feeling homesick!

The perfect summer from now on must contain at least four weeks of holiday. Perhaps I'll test out 5-6 weeks at a time next year.

Self Discovery

This is by far the biggest attribute for making a perfect summer. If you can discover something new about yourself or experience things that really shake up who you are (good or bad), then I say you've done something positive for the long run.

This perfect summer I discovered how I fear being alone as much as I fear being broke. Yet I haven't been doing everything possible to develop better relationships with the people I love.

Instead, much of my effort has been on becoming financially independent as quickly as possible. This will change as I work on being a nicer person who reaches out more often to friends and family.

I also met new people who made me appreciate how wonderful a certain someone is. Taking someone for granted gets unfortunately easier to do the longer you are with them. This perfect summer has taught me how to spice things up again and be OK with routine.

Back To School After A Perfect Summer

I used to have this silly notion that vacations are fun because of work. I can unequivocally tell you after experiencing 12 months of no work and a one month long vacation that vacations are just as incredibly amazing when you aren't getting bulldozed in the office.

It's very easy to take my freedom for granted now that it's in abundance. It's easy to take anything for granted when there's too much. With school back in session, it's probably a good idea to buckle down again after a perfect summer. Going on a year-long bender is not a good idea!

The ability to unwind when you want has always been a core reason for achieving financial independence.  What also matters are the takeaways for continued self improvement.


Negotiate A Severance Package

Never quit your job, get laid off instead if you want to move on. Negotiating a severance package provided me with six years worth of living expenses to help me focus on my online media business.

Check out my book, How To Engineer Your Layoff: Make A Small Fortune By Saying Good-bye. It's recently updated and expanded with even more pages, chapters, tips, and resources of great severance negotiation strategies and real life profiles.

Improve Your Finances

To help keep easier track of your credit card balances, cash flow, bank accounts, and more sign up for a free account with Personal Capital. Their free and secure online software lets you monitor all of your accounts in one place.

In addition, they have excellent financial tools that help you track your net worth, cash flow, and easily plan for retirement. Check it out for free today.

If you enjoyed this article and want to get more personal finance insights and tips, please sign up for the free Financial Samurai newsletter. You’ll get access to exclusive content only available to subscribers.

About The Author

45 thoughts on “To Endless Perfect Summers”

  1. I think experiencing somewhere different is an important part of a vacation. I used to take “staycations” alot. However, I am now really at the point I’d rather be in the office than be home for an entire week doing nothing. I’m all about experiencing something now. The other thing that makes a vacation great is complete lack of structure. When you’re in the usual grind, you get stuck in such a routine. A good vacation, for me, lets me figure it out as I go.

  2. charles@gettingarichlife

    It’s so hot right now but the end of summer means football is back in town! Sam are you making your visit to Hawaii soon?

    1. I always miss Hawaii during the summer. Is it really that much hotter and muggier?

      Might take a trip during December when it starts to get rainy here. But if mango season is earlier, I gotta go then!

  3. My perfect vacation was in early 90’s. Wife and I vacationed on Kauai, drove to the top of the elevation and sat outside. I looked out and down toward the coast and watched the clouds cast shadows on the terrain below and watch whales in the ocean come up and blow. It was at this moment that I had to think hard that I still had a job to go back to. Spiritual monument, almost God-like vistas. I have not had a vacation like that since. I’m hoping that now that I’ve achieved FI that all future vacations will feel that way.

      1. I didn’t make it to 2096 Pine, as it was too hard to park. Instead, I looked at condos/apartments at 1700 Gough, SOMA Grande and the Sutterfield. All the units were pretty nice with recent/decent renovations. None of the showings were busy and I was surprised how hard some of the agents were selling. Maybe the tide is turning a bit. . at least in the short term.

        1. I definitely wouldn’t be surprised if the tide has turned with prices up 15% on average AND the 10-year yield now at 2.9% from just 1.8% earlier in the year. Real estate should slow down big time.

  4. This is our first year in an empty nest. Oldest is a junior and youngest a freshman. Life is a lot less hectic already from week to week. I’ve loved every stage of being a mom, but as hard as it is I’m enjoying watching our girls grow up away from us too. Have to admit I’ve been weepy a few times but I’m loving this slower pace. (This Tuesday is the first time I won’t see my daughter on her birthday and it is her 18th….bet I’ll shed a tear or two!)

  5. To me, that perfect vacation is achieved when I am at total relaxation. Stress from work or my personal life is not even at the back of my mind, and I am just in the moment. This happens the most for me when I am camping an enjoying nature.

  6. MakintheBacon

    Now that I have been working full-time for several years, summers don’t really feel so much like a summer, unless I go on vacation during that time. Taking an online course and helping out with my sister’s wedding took up most of my free time during the summer. I’m hoping next year I will actually have a summer. (Crosses fingers).

  7. Summer of 2006, I was in Eagle River, Alaska, flying King Air 200s. It was a sunny summer (rare in Alaska) and I was done with work around 2-3pm most days. I took up wood working and hiking. I would go home, raise the garage door and finish building a piece of furniture or head out into the beauty of nature to soak it all in. I want that again so bad. Freedom is what I really want, the freedom to do what I want, when I want to and to leave the competitive, stressful, work environment behind.

  8. This past summer changed things for me. I have two kids, 4 and 7. We live 10 minutes from the beach and my in-laws have a house on the bay. Every weekend we went to the beach. Plus, I finally took 2 weeks in a row off from work…it was amazing. The kids and I did whatever we wanted for 2 weeks. We went to the beach, an amusement park, to the pool, etc. I will be taking 2 weeks in a row off again next summer, maybe even 4. I love spending time with the kids and it was exactly what I needed.

  9. I experienced a never ending vacation twice in my life. Once when I was 10 years old, my parents went o Europe for 4 months. I think it started the adventure bug in me. The second time was not a vacation, but the result of achieving financial freedom. It changes your life and outlook. You can choose what makes you happy and pursue it. As a teacher, I have had summers off, but it is not the same. I like to teach and working just 4-6 hours a day seems a lot like semi-retirement. I expect retirement will be different still. I never traveled for more than 3 weeks at a time as an adult.

      1. It was a great time to travel because I sought other children my age. I learned language, culture and more from them. I still remember many of my experiences after all these years.

  10. Tara @ Streets Ahead Living

    I haven’t had a really fun summer since college. I yearn for the days in which I can just go to the beach every weekend (too busy now).

    Glad you got to experience the Open! I’ve lived in NYC for 6 years and I have yet to go sadly. Some day soon…

  11. Insourcelife

    When I was younger, summers seemed so long and now they are just a blur. It’s already September, pool is closed so the summer is over yet again. Working gets in the way of enjoying what summers have to offer, just another reminder why we all need to be able to “retire” early… or at least take a couple months off every year to do whatever it is that floats your boat.

    1. Indeed.
      When things are a blur it’s usually because there was too much going on or that nothing really memorable occurred. Gotta make time for those moments, good and bad!

  12. I’ve only really had 2 perfect summers in 29 years. One actually involved working all day at a crappy job becasue it made the nights in between that much more of a blast! Unfortunately now sneaking away for even a week seems implausible most times and when I do it seems the task list for getting things done eats up most of the time I get. Next summer is already spoken for and almost won’t exist. Not the brightest future to look forward too, but there is sunshine on the horizon ina few years.

      1. Unfortunately my job comes with an almost unthinkable number of training requirements. It seems like you spend a good portion of your time looking for space between those “mandated” training dates to take any kind of lengthy vacation, and on the off chance you find 6 or 7 days magically out of thin air a travel assignment pops up that I am magically the only one qualified to attend, and thus vacations are continually pushed. I had planned to try and get away to see my wife at least for a 5 days a month (opp coasts) and it looks like that plan will only be effective for the first month, afterwards training and trips will keep me away for the next 3 months before I leave for an overseas trip for the next 6 months. Just keep telling myself that all the pushing will lead to something great ont he day I can look at my returns and say I can take that magical 4-5% a year without touching principal and accept a severance check and enjoy a long break from responsibility.

  13. Your summer sounds amazing. I’m a little jealous. Do you rent out your house when you travel for long periods of time? I might take a sabatical between jobs and do just that.

    My summer has sucked – been working 70-hour weeks. However, I’m leaving tomorrow morning for a 10-day trip to Hawaii that will culminate in a friend’s huge beach wedding, but the first 8 days are entirely unplanned – I haven’t even decided what island to relax on yet – alone, spontaneous – the possibilities are endless. It will be perfect end to an otherwise painful summer.

    1. I don’t because I haven’t gotten over strangers living in my home.
      But after seeing so many friends airbnb their apartments in NYC, maybe! They all rent though so the feeling of attachment is a little different.

      AirBnbing a rental feels like you’re getting something extra for free. Airbnbing your own home is more of an exchange.

      Enjoy Hawaii!

  14. A perfect summer or vacation for me is being able to relax, really relax, with people I care about with all the stress of figuring out what’s next. For me, that usally means spending the days at the beach laying out, swimming, and surfing. Quiet and relaxing!

    This summer, I haven’t spend much time at the beach or surfing! That’s mainly because last year I injured myself while surfing and haven’t been back! Although, I’ve been thinking about it lately. Maybe it’s time for a quiet vacation near the beach. I live in Florida so that’s not hard to do! Even so, it’s starting to get cold here so time at the beach will be limited soon.

  15. This last two summers have been amazing for me too. It’s not the same as when I was young because I have a kid tagging along. It’s very different, but it’s just a ton of fun. We didn’t go to any amazing places, but it was still a great time.
    When he’s a bit older, we’ll travel more. It’s a lot more fun now than when I was working and traveling internationally. It’s difficult to compare, but I feel more well. (wellness?)

  16. I no longer crave having summers off like i did in school. I just crave vacation all year round. If I can take a week long trip every 2-3 months I’m feeling pretty good. I’ve had incredible trips in the middle of winter, in the spring, etc. it doesn’t have to be 2 months off all at once during the summer time. But hey I wouldn’t mind having all that time off either if I had the luxury of having it.

  17. The last few summers have been amazing. I would tell you about them but you would think I’m lying.

    I agree with your notion though. Self-discovery, new destinations, and people MAKE a summer or a trip into an instant classic. I’ve met some of the biggest characters in the world, fell in love on beaches, and discovered places I never thought could possibly exist.

    Congrats on the great summer!

  18. Given that I have three kids, I think this question becomes far more complex. I routinely work on self-improvement, but that necessarily involves always working to be a better father and husband, though that also seems to compete many times with the space I need to be reflective. I haven’t mastered this balance yet and I’m not sure I ever will completely.

  19. Very timely post Sam…first of all I’m blessed because each night I come home I basically see the picture you have posted for this article out my back window. Absolutely stunning, usually grab a beer and go sit on the end of the swing and soak it in for a while…even though this summer has been the best in recent memory, I can’t help but to think I should have found a way to have taken even more advantage of it.

    Quick question…when you refer to your or “the” ideal burn at $200k/year is that after tax dollars?

    1. I refer to $200k as pre tax dollars or operating profit for business owners.
      Good steady state that can basically allow one to live wherever however they want without having to kill themselves to achieve the income. Marginal utility In return and happiness really declines after that I’ve found.

      Hope you found someone to spend those summer sunsets with!

      1. So I pretty much agree with the $200k target and never touching the principle. So when you pulled the plug and retired do you consider income from any means (Rent from properties, investment income, online business, etc.) or are you really just basing it off building your new business to generate $200k…the wording confused me (cause I’m not that bright, not because you explained it incorrectly) in a couple of your articles. This was one of those tough weeks for me where I think about pulling the plug since I already live off less than what one of my commercial properties throws off in cash each year. I’m sure next week though will be one of those close a huge deal and be on top of the world weeks.

        & yes thankfully I have somebody to share the sunsets with, last night the colors over the water were spectacular…now it’s off to tailgating…damn I love the fall almost as much as summertime!

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