Do You Work Harder Or Relax More During Good Times?

Work harder or relax?

There's an old saying that one should, “Make hay when the sun is shining.” Do you work harder or relax more during good times? When I was in my 20s I had two modes of work ethic. 1) Work hard and 2) Work harder. I'd wake up around 4:30am every morning in NYC from 1999-2001 to read the Wall St. Journal before walking over to 1 New York Plaza for work at 5:30am. I knew knowledge was power and I had neither.

After the 10 year mark, I began to burn out. Perhaps all the traveling, stress to perform, ridiculous market cycles and business school classes while working started taking its toll.

I did everything I could to increase financial returns when the times were good because times would eventually turn sour. When times were bad, I felt I needed to work harder so as not to fall too far behind. People were getting fired left and right back in 2001-2003 and 2008-2012.

Ask anybody who has worked on Wall St. since the late 90s and they'll tell you that 2007 was the last great compensation year. It's been downhill ever since. There was no longer hay to be made, even if we are reaching new highs in the stock market.

Did I always work harder or relax? I woke up to the realization in 2010 that the outsized returns in finance were over, at least for the foreseeable future. So instead of complaining about working harder and getting paid less each year, I got out in 2012.

A Change Of Heart To Working Hard

At 36 my work ethic has changed. It became 1) Work hard for the things that truly matter. And 2) Make sure my money is working for me so I don't have to. There's no more “work until you drop dead” type of mentality.

Probably the biggest conundrum I encounter on a regular basis are complaints from people who are unhappy with their existing financial situation, but who aren't doing everything possible to improve.

There are actually people out there who only work 40 hours a week or less who complain about their financial situation! Why not just try harder to get ahead? Why attack someone who has what you have instead of working on yourself? We are only owed what we deserve.

Should you work harder or relax when you don't enjoy your job?

Working at a job you don't enjoy to make money to survive is very depressing. You're a slave to your needs and wants. The hope for my book is to empower people to stop being too afraid to run out the door. Waking up 12 years later filled with regret about time wasted is horrible.

The key is to build a big enough financial nut that matters. There will be an inflection point where you start making enough money from your financial nut that you no longer need to work as hard or work at all.

We are talking about principal gains to your portfolio and not passive income streams. Just imagine if you had $2 million invested in the S&P500 index on Jan 1, 2013. You would be up around $500,000! The same goes with holding similar amounts of real estate in markets such as Vegas, Oakland, San Diego, San Francisco, and Seattle.

Work harder or relax?

Of course it's much easier said than done to amass a large financial nut and actually have the guts to invest the money. But the point is that if you are a hard worker who can't ever seem to relax beyond the normal vacation periods, your mindset will eventually change the more you accumulate.

The value of time begins to trump the value of money as you no longer feel good chasing the all-mighty dollar. Do not kid yourself. If you are working at a job you don't enjoy, even if you don't make a lot of money, you are a dollar chaser.

You Need Less Thank You Think

The biggest discomfort for those who decide to relax when times are good is the fear of losing ground. Why not make lots of money in your investments AND at work? There's really no limit to how much money you can make. We've just got to decide for ourselves how much is enough to be happy and stick to that figure.

Now that I've been out of the work force for almost two years, I'm becoming more enlightened to the fact that it's absolutely crazy to work so hard at a job for money if you aren't happy at least 70% of the time.

If you're making at least the median income level for your area, you need much less than you think to enjoy life. I promise you will be much happier working at a job that pays less, but provides more satisfaction than at a job that pays 50% more but makes you dread coming to work.

The “one more year syndrome” is so difficult to break. But when you do, you'll wonder what took you so long.


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. The book is recently updated if you want to learn how to negotiate a severance package and do your own thing.

Start your own business

One of the best ways to make more money is to take matters into your own hand and start your own business online! It used to cost a fortune and a lot of employees to start your business. Now you can start it for next to nothing with Bluehost.

Brand yourself online, connect with like-minded people, find new consulting gigs, and potentially make a good amount of income online one day by selling your product or recommending other great products.

Not a day goes by where I'm not thankful for starting Financial Samurai in 2009. I have maximum freedom now thanks to working on my side-hustle while working for 2.5 years. You never know where your journey will take you!

Updated for 2020 and beyond. The 11 year bull market has so far been amazing!

49 thoughts on “Do You Work Harder Or Relax More During Good Times?”

  1. Saw this quote from Machiavelli and thought of this posting:

    “A wise prince ought to observe some such rules, and never in peaceful times stand idle, but increase his resources with industry in such a way that they may be available to him in adversity, so that if fortune changes it may find him prepared to resist her blows.”

  2. That’s a tough question. Having a great month definitely gives me motivation to work harder. But after several long nights I don’t even want to turn on my laptop once all my work is submitted.

  3. When I paid off my home and hit a net worth of $700K (not including the home) in my late 40s, I started to value extra free time more than extra money. And I was able to reduce my hours at work by taking every other Friday off (a 10% pay reduction) and still retain full benefits. So, in effect, I get 26 unpaid days off + 15 paid days off.

  4. The Phroogal Jason

    I learn like you I needed less than I thought. My mentality has changed as well. I no longer work harder I work smarter and make sure my money works harder for me. It’s a definitely better way of making sure I spend my time on things that matter…my family, friends and experiences.

  5. Sounds like you are working smarter for sure. In the finance industry, it’s like a badge of honor to suffer as much as possible through long hours. Bosses want their underlings to suffer just as they suffered for the big bucks!

    1. Bingo!

      90%+ of all jobs are like this. It’s all about showing up.

      I would bet the actual productivity is more like two or three hours a day (especially if you waste time in pointless meetings!).

  6. I think I do work a little harder during the bad times than the good times. I believe in the adage “Buy when there’s blood in the streets” and it’s served me well. But at this point, my biggest goal is to slow things down a little more each year so I can avoid burnout and enjoy the journey a little more.

    In my energetic 20s and 30s, I was definitely in the same camp as Sam, running only on two gears; “fast” and “faster”.

    As for getting left behind, it doesn’t really enter into the picture since nearly all of my friends have been doing very poorly for a long while. So, I usually just keep an eye on my numbers, try to do better than the year before, and hire things out to scale up and generally get myself out of the picture (i.e. rehabbers, property mgmt. companies, accountants, handymen, etc.).

    I definitely want to stop working as hard as I have been, but I’m nearing a tipping point of sorts. There are a few specific moves/deals that I want to do and if I cut back / change things immediately, some of them would be delayed and some would be off the table completely.

    I hope to complete these in the next 2-3 years. After that, I want to take a “trial retirement year”; keep working as usual, but bank 100% of take-home pay and try to live solely off of passive income. This will be the final litmus test of my plans for FI. If I’m able to survive without “putting my hand in the cookie jar”, it’ll be a huge confidence boost. Assuming that’s successful, it’ll be time to close up shop, do some traveling and really think about what I actually *want* to do with my time. To date, though, nothing has come to mind…

      1. I don’t think it would be good to share details, but I’m fairly certain that’s not what’s happening. This year, though, things seem to have improved over the past few years for many of them. So, I’m hopeful.

  7. It’s possible that I might be part of the Small Business owner’s group soon, and I wonder what my schedule will be like. My purpose isn’t to get rich, but to have more flexibility. But I know that my competitive, perfectionist nature won’t be able to just kick back at 4pm and enjoy the rest of my day.

    1. The Phroogal Jason

      It’s definitely about the non-monetary rewards one gets. You can work really hard (24/7) but if you aren’t doing what you really want to do then it really isn’t worth it. If it’s taking you away from things that matter than it isn’t worth it. The first step is really finding out what matters in one’s life then find the ways to enhance those experiences.

  8. I find it hard to relax. When I was in Argentina last week, I would feel guilty if I didn’t write or respond to emails. I always feel anxiety and the need to be getting more done.

  9. That “one more year” problem is something I’m sure I’ll be facing… You’re right, it is difficult to shake b/c if you’re still employed and earning income and have passive income on top of that, you’ll probably be very reluctant to give that up. Not gonna lie, it’s empowering to see income stacked on top of income being deposited into your accounts each month.

    When times are good, I think you work less… you’re more able to get away with things at work. When times are bad, everyone is on high alert and working till midnight trying not to get canned. As an investor, the “once in a lifetime” deals emerge during the downcycle… so in that sense, you probably should put in more work/effort in trying to secure these deals. You must do this if you those $500k pops you referred to. Very difficult to find these when times are good.

    1. It’ll be interesting to see what you will do once you meet your passive income goal! My bet is that you keep on going for several more years b/c you have the energy and you like gravy!

  10. Ah….. The rat race……

    Life is short. If you really find your occupation so unbearable; do something else! Or, at least find an interesting sideline/hobby.

    My opinion is that working excessive hours will eventually lead to burn out in most people (and a higher income tax bill). Throw in a long commute and a damaged psychology is a given.

    People need balance.

  11. I’m currently between a rock and a hard place myself. On the one hand, I can quit or at least take much fewer hours at the moment and be fine. On the other, I’ll be sacrificing income for time spent doing hopefully better things but maybe not. It’s a tough decision because I don’t want to be stuck doing nothing. Working harder is just burning me out and making me hate what I do. I’m a firm believer that if you hate where you are you should change, even if you somehow end up worse off.

  12. Christine M.

    Is that you in the picture Sam on the beach? If it is…why not be a stand-in for Channing Tatum on the next “Magic Mike” movie and make some really big cash?!?!

  13. I’m a lawyer and currently work in a big firm with a bunch of other lawyers (many of whom have the one more year syndrome) – I think the problem with many is that some people who work too hard and have too little free time may feel like they need to really ‘go big’ with whatever limited time they allow for themselves in their pursuit of happiness, and then they get stuck in this cycle where they have to keep working like a slave to afford the fancy car, big house or new wife, and they are so overwhelmed with keeping up with everything they’ve got, they’ll never break out of the cycle. Seems to be a trend. I think it is a way of dealing with a form of depression and I think it snowballs.

    1. Yeah, I hear you 100% on this one! Same thing goes with bankers. Go Big on vacations and stuff to make all the hard work seem worth it!

      With Law though.. man, school is so expensive and for 3 years. I would feel I’d need to work at least 15 years to feel like I got my money’s worth.

  14. Maybe it’s my personality but I don’t see how people can be go, go go all the time. I have to build in time to relax and rest to make my work life more productive and my home life more enjoyable. My father-in-law literally worked himself to death. Owned a restaurant in South Florida and never wanted to hand over control of even minor operations of the business to a manager. He was there from 11:00 am until 3:00 am the next day, 6 days a week. Late one night after cooking someone’s dinner he felt dizzy, walked out the back door of the kitchen and collapsed, dead on the spot. I have no doubt his crazy, pushing lifestyle contributed to this. I don’t want to live that way and I sure don’t want to go that way.

    1. Some people have simply much stronger endurance than others. Sorry to hear about your FIL. I do wonder if your father-in-law would not have been happy NOT working so hard. We do what makes us happier in the end no?

  15. I’ve tried not to get myself in a position where the job pays well but I hate my job. 8 hours is a long time during the day to be miserable. You already spend 1/3 (or should be) sleeping so if you aren’t happy at work, you aren’t leaving yourself a lot of time to enjoy life. Given how unpredictable it can be, might want to enjoy it while you can.

  16. Thanks for this article.

    Reading a bunch and teaming up with the people I trust and respect is necessary – and expected – in order to not fall behind, whether the pressure is on or not. In order to manage fear I ever-prepare for opportunity by seeking out resources, developing awareness, cultivating my relationships, and finding ways to be creative and thankful. For perspective, I reflect on where I came from. Per request, my mentor advised me on how to maintain long term happiness at work: every morning I wake up and make the choice to go into the office, not for where I hope my career will go or the paycheck I will receive, but for the Idea I will get to chase. It takes relentless effort, big picture planning, and calculated risk to do what you love and get paid well for it. There really are no breaks – just new goals and milestones to work toward.

  17. Some people can follow this advice and be both successful and happy, but I suspect there are quite a few who had better just hold what they have and be thankful for it, even if it isn’t making them completely happy.

    Not everyone has the chops to make a successful transition.

    That said, if they do exactly what you say here– establish their minimum nut and work and grow their assets to facilitate the move, then I can’t see how this doesn’t make sense. Few seem willing or able though.

    As you know, I’m trying very hard to get there myself.

  18. Done by Forty

    There’s that concept of ‘enough’ again. Probably the most important concept in PF. How much wealth is enough before you ease up or walk away? How much income is enough before you reach the point where time becomes more valuable than the earned income?

    I personally am trying to work hard now in a race to FI, but the plan is to ease back or walk away at that point. Admittedly, this makes me a short term dollar chaser. I’m okay with that…for a while.

  19. Your comment of “Why attack someone who has what you want instead of working on yourself? We are only owed what we deserve.” rings so true with me. There a few people who read your blog and comment here who want to rip on people who have more…they think we were just “lucky”…drives me crazy that people want to tell you that you are selfish and should spend your money a certain way when just because you have success. Nobody was jealous of me when I was working 110 hours a week for years in a row, but now I’m a jerk because I can pay cash for a nice car using a portion of my passive income.

    You make a great point that I agree with…life actually is pretty damn cheap to live, I’m happiest when I’m taking the time to travel and exercise consistently. As long as you don’t inflate your lifestyle as your income grows and keep life simple you’ll be happy. I know friends with similar net worth’s that will only fly private, or belong to 6 country clubs…hey I say great, live life how it makes you happy!

  20. The First Million is the Hardest

    I think its natural to relax more and slow down when times are good. If everything is going well you’re probably feeling more content. Whereas when times are a bit rough you’re more motivated to work your ass off to try and change things.

  21. Pura Vida Nick

    I absolutely agree that “If you’re making at least the median income level for your area, you need much less than you think to enjoy life. I promise you will be much happier working at a job that pays less, but provides more satisfaction than at a job that pays 50% more but makes you dread coming to work.”

    I have personal experience with this. I really enjoy my job – I feel that I truly help people and people are grateful for what I do. I don’t dread coming to work. I make about the median income for my area. It’s easy to start dreaming of make more (who doesn’t want to make more money?), but I always come back to reality when I remind myself that I do enjoy my job, and I don’t want to make more money if it would mean dreading coming to work or even if it would mean being less happy.

  22. Blake @ BeanCounterByDay

    One of the biggest pet peeves of my life is people who complain and then do nothing to fix their problems! I know several people who are always complaining about their financial situation, but then they’re sitting on their butts watching TV during their free time instead of figuring out a way to fix it. I actually had a distant family member contact me the other day to help him figure out how he could become tax-exempt from federal taxes so that he had more money!

    I’m 30, and I share your philosophy whole-heartedly. Work hard until your wealth accumulation can take over some of the work for you! I’m up at 6am every day. Certain days I work on side-jobs, other days I just get up and read everything I can that might somehow be beneficial. I still have all the time in the world on the weekends to enjoy life to the fullest.

  23. Justin Gesso

    Great article and a very good read for those of us who have been in a “shrinking” corporate environment. A lot of companies these days are making regular and deep cuts. In order to strive, you have to do better, work *more*, promote yourself, and effectively marry the organization. You generally get rewarded financially, but you also continue to pile on the work of your fallen coworkers. So it’s a pretty crazy path that ends in stress, hours, more stress, and more hours!

    I recently pulled the plug to head out on my own, thanks to the inspiration I’ve found here and elsewhere.

  24. I am in the mentality of working smart and investing my money to work for me. I work less than 40 hours a week and make good income because I run a business and hire people to do the crap I don’t want to do. I continue doing the things I like doing and take plenty of time off. I invest my money in Real Estate and the cash flow is great. I can’t wait for 5 or ten year when the cash flow is more than enough to live very happily. In the mean time I think being happy is incredibly important.

    1. Same here. I don’t think I can do what Sam did in his earlier years. I always have to have work-life balance, especially being a mom. Otherwise, I think I’ll lose my mind.

      I was fortunate to have had a good-paying job (and a good financial education) in my 20s, so I was able to work, save, and invest as much I could. I channeled all that money into businesses, real estate, and cash investments. Everything I sowed has thankfully paid off, and now, I can focus on raising my children without sacrificing so much.

      That said, I don’t think I work harder when it’s “good times”, but rather I strike while the iron is hot. I try to make as much money I can while I can. Now, I’m at a different season in my life, but I’m very grateful to my younger self for putting me in this comfortable situation I am in.

      1. “Do you strike while the iron is hot?” Could have been this play’s title too. We are very similar.

        Glad you get to spend more time with the family! What is it you do and how old are you?

      2. Kudos to you Ikaela! You are not alone. I was going to comment below, but you have said almost word for word what I would have typed! It was nice that someone in my upbringing noted that time is your best friend when you are young – use it wisely and you will live the happy life. I am a retired father of a 10yr old, and love nothing more than being able to be part of his growth. If the right iron presents itself, I might become unretired, but until then, I’ll just enjoy life and work on ensuring he has all the opportunities to succeed at whatever path he follows. – Cheers.

  25. I go through waves of motivation bursts but I tend to want to consistently over perform. A lot of my work load is at the mercy of client demands, so if they say jump I’m figuring out as fast as I can how high. Most of the time I can keep a good work load balance but it does take a conscious effort not to let stress build up. I think I’m doing a better job of not letting things get to me like they did earlier in my career.

  26. Sam,

    I work in a very cyclical industry. I happen to like my job when times are good. I love trying to cram 10 hours of work into an 8 hour day. When times are slow, the job is not as fun. So when it slows down, I take as much time off as possible. I get 5+ weeks of vacation a year. I take all 5 weeks every year, usually during the slow times. When things are really slow, my company shuts down for a week here and there. Most people who live check to check have to use their vacation time to get paid during this period. I found that taking unpaid time off during these shutdowns was an option per company bylaws. While I am not really 100% FI at this point, I am nowhere near living check to check either. Last year I had 11 weeks off between taking the shutdowns off unpaid and preserving my vacation days. It is like having a part time job with a pretty much full time salary. I LOVE it! Now I look forward to the good times when work is fun and I look forward to the slow times when I travel. Win-Win for me.

    1. 11 weeks off is a great amount of time off. Lucky your company is good with that. Wall St. companies would mega vacationers go in the next round of layoffs for sure. I did 6 weeks and that was really pushing it.

  27. I don’t know, I read the paper this morning and there appears to be other alternatives. Fast food workers want to double their salary without any extra work. It’ll be interesting to see how that plays out. Will the squeaking wheel get the grease? If so, Wall Street workers better start bulking up if they want to strong arm their mega-corps.


    Las Vegas

    1. “I worked at McDonald’s for nine years. Because when you love life, life loves you back.” – Mike Lawrence

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