After 12 years of FIRE (financial independence retire early), I went back to work. Unfortunately, I only lasted four months. Here's my story of what went wrong. I purposefully waited months to release this post to ensure I was thinking logically and not emotionally.
From the end of November 2023 through March 2024, I re-entered the workforce. Having worked 11 years at my last full-time job from 2001-2012, I was disappointed I couldn't even last a year.
When I decide on something, I always try to give it my best before moving on. However, after four months, I decided I had enough.
This post is a journey of self-discovery about the difficulties of going back to work after a long time off. It also provides insights into how age and wealth change your tolerance for work. Hint: it declines.
Working for a company is like a marriage. You date through multiple interviews, and both sides take a leap of faith if they see potential. However, like many relationships, they don't always work out.
The silver lining of having a short stint at work is that I now better understand what I want to do next time. Additionally, I know that I can return to work for a decent salary if I choose to. It can be difficult finding a good job after retiring for years.
Background On Why I Went Back To Work
I had been seriously considering going back to work since April 2023, when I penned my post, “Sadly Giving Up On Retirement By Going Back To Work.” After experiencing work freedom since 2012, when I left my day job in finance, I was looking ahead to the future.
At the time, many readers thought I was joking, but I was serious. I had calculated the cost of college in 2036 and decided I should probably start generating some extra income to afford such an enormous future expense. We're talking around $450,000 for four years of public college and $750,000 for four years of private college by then, and I have two children.
I read a lot of research about the affirmative action Supreme Court case that seemed to demand higher academic excellence, extracurricular activities, and even personalities for Asian applicants.
There were countless examples of Asian kids with excellent grades, test scores, and activities getting rejected from top colleges. As a result, I concluded it was probably best for me to earn more money for my kids, given they are unlikely to get any grants or scholarship, even if they excel.
I half-heartedly looked around that spring and summer but didn't find anything interesting, so I shelved the idea until November 2023. That was one month after we bought an ideal house for our family. Suddenly, the need for more money shot through the roof!
Actions always have consequences. Instead of complaining, I forced myself to look for a work opportunity through my network.
The Job Opportunity
I was feeling the financial strain of having less passive income and an empty previous house that wasn't generating any rent. So, as any rational person would do, I decided to look for active income opportunities. I sent a feeler out in my newsletter, and a long-time reader and ex-colleague reached out and introduced me to a fintech startup in San Francisco.
I met the team, thought they were great, and received a good offer for roughly 20 hours a week of work. Even though I was part-time, I was given a founding role as the head of content at this startup, along with equity. I was grateful for the opportunity and their flexibility. Truly, I thought it was going to be a great match.
My goal was to last a year until November 2024 and renegotiate for a full-time role because I hoped to love the work. By then, my daughter will also be in school full-time, meaning I will have more time.
I imagined naturally weaving this company's product into my writing on Financial Samurai, given the synergies. Given I write everything from firsthand experience, the organic mentions would be a boon to the company looking to gain traction. The work was remote, but the founders were in the office around three times a week, so I went in once a week for the first month.
Why I Could Only Last Four Months In My Part-Time Consulting Role
Out of respect for the company, I won't mention the name or the people. This post is not about criticizing them as they are good people and the product has great potential. Instead, this post is intended to help those who are thinking about going back to work, or shifting to consulting work, make better employment decisions.
After all, many people who FIRE tend to eventually have an itch to return to work in some capacity. Maybe they're bored and are looking for camaraderie. Or perhaps their net worth took a hit after a bear market.
Additionally, this post will highlight some of my personal flaws in hopes I can improve. Overall, I think 70% of the reason why I failed to last longer than four months was due to me, and 30% due to the CEO/company. Here are the reasons why my work stint was so short:
1) Part-time Consultant at a Seed-Stage Startup Is Not A Great Fit
When you're at a seed-stage startup that hasn't launched its product yet, the work is endless. After about a month, even though I delivered on all my requirements, it didn't seem fair to the team that I was part-time. The company deserved someone full-time.
Because I felt this way, I ended up working almost every day of the week instead of on our agreed-upon Monday, Wednesday, and Friday schedule. There was always so much to do. The 20 hours a week we agreed upon quickly grew to at least 25-30 hours a week.
Over time, the emails, Slack messages, video meetings, and interviews on my off days began to wear on me, as they interfered with my time with my daughter.
Too much interference with personal time
For example, one Tuesday (off day), I took my daughter swimming for a regular 3-hour outing. But because I had agreed to a meeting that afternoon, I had to cut our swim session short. Instead of having a sit-down meal at In-N-Out Burger afterward like we normally do, I decided to go through the drive-through to save time. However, the line took forever, and I started feeling highly agitated given I didn’t want to be late.
What was supposed to be a relaxing day with Daddy turned into an anxiety-filled one instead. I'm not one to ignore messages. If something needs to be done, I will do it, even if I'm supposed to be off. But because I've been used to being a full-time father for 7+ years, if something hurts the quality time I have with my children, I probably get much more agitated than the average dad.
You can be a part-time consultant for an early-stage startup, but you might not last long either. During my four months, two other contractors left. But it seemed like they had a set work duration or work goal.
Early-stage startups are looking to save money and be as scrappy as possible. However, the equity reward I was given wasn't enough to motivate me to consistently work beyond expectations.
2) Difficult to Work With So Many Meetings and Slack Messages
Before joining this startup, I never used Slack. In fact, one of my quirks is that I keep my iPhone on sleep mode almost the entire day so I'm never hardly bothered. My WhatsApp and messages don't alert me when new notifications come in either. I check my messages when I'm free, and that's the way I've liked to do things since 2015.
I've developed this habit because I require no distractions in order to write. The need for peace is why I'm often writing between 5 am – 7:30 am and after 9 pm. These are the times when the house is quiet.
Unfortunately, my Slack messages were constantly going off. I tried putting them on silent, but then I'd miss some notifications from the CEO. After missing an event because I hadn't responded for over two hours, I turned on my notifications, which then hurt my productivity.
In addition, I'm not used to being in meetings, especially not 6:30 am meetings. As a result, I find meetings that last longer than 15-30 minutes to be unproductive. However, the reality is, meetings need to happen to get everybody on the same page to get things done. Hence, it's my bad for not having better meeting endurance.
The thing is, if I'm in meetings or on Slack, I'm not writing. And my job was to write and edit pertinent content for the product. I'm not as bad as Jack Nicholson in the movie The Shining. However, I can empathize with his annoyance in this classic movie scene below!
3) Lost My Voice And Personality As A Writer
I write because I enjoy the process. It's fun to write freely in my unique style. However, my personality was stifled by the CEO's heavy editing. I understood what they wanted but could never quite replicate their desired voice, even after 20 articles. My writing was either too complicated or “sophisticated,” or not “cool uncle” enough. After a couple of months, the constant heavy editing after my pieces were already edited was demoralizing.
After a couple of months, I could tell the first-time CEO, was getting frustrated too. So, I asked my wife to try writing the articles in the CEO's desired voice, with me reviewing and editing her work. This approach worked better, and I felt we had a good solution for dividing and conquering different types of topics between us.
However, my joy for writing began to fade. I didn't have control of the editorial calendar as expected, which would always change despite agreeing on the plan the week before. It felt jolting to pivot so much last minute, which is my issue for not being more flexible.
Didn't want to provide the same critical feedback like I was getting
In one instance, the CEO wrote a personal article that needed more structure and action points. However, I dared not make more than a few suggestions, fearing I might offend them. So, I basically said the article was great as is, with suggestions for creating some subtitles for easier readability.
My hope was that by empowering the CEO with minimal suggestions for change, they would notice the large difference in editing styles and also empower me with my work. Unfortunately, my articles still ended up getting 50-100 edits each, which became comical at times. There was simply too much nitpicking that didn't matter. The editing hurt efficiency and lowered my morale.
Funny enough, a couple of the sections in articles we published, written by the CEO, were questioned and criticized by an Aw nope employee with little filter. The employee thought I had written those words. This shows how subjective writing can be; five people can read the same article and come away with five different opinions.
This example also highlights the power dynamic at play, where employees are fearful of making suggestions to those in power but not the other way around. I had largely forgotten about this power dynamic since it has been so long since I had a boss.
4) I Got Managed Way Too Much
If you haven't had a boss in a while or are financially independent, you might have a lower threshold for taking orders than in the past. I fully admit my threshold for being told what to do has declined since my 20s and 30s.
The CEO and I had a video meeting once a week and often two catch-ups throughout the week. This isn't a lot in the grand scheme of things. And perhaps most employees would find all this face time with the CEO rewarding. However, I preferred fewer meetings and mainly wanted to execute the game plan for the week. Again, if I'm in meetings, I'm not writing.
With a plethora of things for the CEO to do, I felt bad each instance they had to spend time giving me guidance after the first couple of months. Instead, I hoped they would just let go and trust my experience and expertise. This was my expectation when I first signed on. But it never quite happened.
Understandably, the CEO of the startup wanted their imprint on everything I produced. It was their company. However, I also believe a good CEO knows how to trust their employees and delegate. Let people be experts in their field do their thing.
5) Started Noticing My Colleagues Were Too Busy To Care
Like most people, I appreciate praise for a job well done. While working in finance for 13 years, I used to keep a subfolder in Outlook of nice e-mails. The hours were so long that it felt good to revisit kind words from bosses or colleagues on occasion.
Unfortunately, it seemed as if only about one out of every three articles I wrote was read by my small team of colleagues. Although one new hire was great in reading and providing helpful edits with almost every post. One senior employee might have read only one out of every 10 articles I wrote. This was even after I was encouraged by the CEO to highlight the posts in Slack.
Being ignored never feels great, and I'm probably more sensitive than others as a creative, since we constantly risk putting ourselves out there.
Even after I asked my colleagues to listen to and rate a relevant podcast that would help the company, none of them did. Leaving a review costs nothing and requires less than a minute of time. The funny thing is, I'm the only one to review their newly launched podcast so far. This mismatch in review support felt off.
When you start sensing your coworkers don't have enough time to care about your work, you can't help but stop caring about their work. It's a slippery slope that needs to be arrested. There's a reason why they hang “Employee of the Month” plaques at McDonald's!
6) The Comment That Broke the Camel's Back
Almost four months in, I was actually feeling pretty good about everything. I had dialed down my sensitivity towards the heavy editing of my writing and the indifference by some of my colleagues. I recruited my wife to help out with the writing and editing of some articles, which felt great as I've been wanting her to get back into the workflow. It also felt like the CEO was giving me more leeway to control the editorial calendar.
As head of content, I also launched their weekly newsletter. I thought I was doing a good job given the high click-through rates. Like all my articles, the CEO reviewed and edited all my newsletters. No problem. We had a good system going.
Then, one afternoon, I got a stern Slack message from the CEO saying something like, “You didn't include the proper links to the articles. Be more careful next time as I expect you to have the newsletter ready to publish when I review it.” This was a normal request, but felt different than usual.
Unfortunately, that was the message that broke the camel's back because I thought we were supposed to be a team. The CEO had been heavily editing and revising all my work since the beginning, always changing the final copy of the newsletter as they saw fit. So why were they suddenly going from a collaborator to a criticizer? I responded with a, “Will do.”
An editor is supposed to help check everything and make the final product better. I went from feeling like we were a good team to feeling like a failed soldier, despite scrambling to get this newsletter done last minute as it wasn’t on that week's agenda.
Deciding to Make a Change
Maybe the CEO was having a particularly stressful day. Or maybe I'm too sensitive. I decided to sleep on my displeasure to see how I'd feel the next day. And the next day, a Tuesday, I sent the CEO the message, “Hi X, this isn't working out.”
They wanted to talk that day, my day off with my daughter, but I told the them let's chat the next day when I'm back on. Then on Wednesday, the CEO decided Thursday would be my last day.
I thought they might have wanted me to at least finish my responsibilities for the two-week sprint we decided on that Monday. Or perhaps, they would have proposed a different working arrangement so both sides could benefit. We were only a month or so away from launch. But instead, it was sayonara.
The departure felt impersonal and sudden. During the exit call, any warmth the CEO used to have disappeared. What an unceremonious ending to what could have been a great long-term partnership.
Would Have Lasted Longer At Work If I Had More Free Time
If I were in my 20s, I would have sucked it up and kept working for at least a year. I remember being great at smiling at my bosses while gritting my teeth. I also would have come to the office once or twice a week to develop stronger relationships, even though I couldn't write if I was talking or in meetings.
But something also disrespectful happened, which made me decide to stop going in weekly after a month. Now that I think deeper, this disrespectful event permanently changed my enthusiasm for consulting with the company. I'll share the story in a future article when the time.
If I had started this part-time consulting opportunity after September 2024, when my daughter starts school full-time, I believe with an 80% probability I would have lasted at least a year. But with too much work bleeding into my off days, I had to quit. I needed to cherish these final days at home with my daughter as I'm going through a parental existential crisis.
The below quote and video encapsulates my remaining time as a father well. “You will spend the majority of your life knowing your children as adults. But for a brief moment, you get to know them as children.”
Parental Guilt Can Be Overwhelming
Through this work experience, I've realized I have more dad guilt about being away from my kids than I thought. I assumed it would be easy to work again since I have stayed home with my daughter since she was born in December 2019. Instead, it's precisely because I've spent so much time with her that I feel so bad not spending time with her when I can.
I experienced this dad guilt again when fellow dads planned a trip to Mexico for four nights and four days. I thought I'd be thrilled to go drink tequila, play golf, and go deep-sea fishing without my family. But I have a difficult time choosing to spend time with anybody else besides family for that long, given we're always together.
Deciding to work for money over spending time with your children while they are young is tough! My colleagues have to be amazing, and the work has to be world-changing for me to continuously make that trade-off. Alas, as an older parent, you are more sensitive to the disappearance of time.
Feeling overwhelmed is common as a parent. And as a retiree, I've learned that feeling overwhelmed is an unexpected challenge of retirement. It's up to you to set boundaries so you can remain in your desired state of happiness.
Money Matters For How Much You're Willing To Work
I went back to work partly because I'm on a journey back to financial freedom. My choice to buy a house I didn't need necessitates a rebuilding of my passive investment income.
But I also want to be part of a great work team again once both of my kids go to school full-time. I used to love battling for business together with colleagues, growing in my role, and going to happy hour after… or so I thought. Then my financial situation improved.
On February 1, 2024, I found tenants for my old house. That provided a lot of relief after the house sat empty for almost four months.
Then I received a surprise real estate capital distribution of $106,000 on April 11, 2024. It gave me more confidence to speak up about my suboptimal work situation.
Meanwhile, there were crazy bidding wars for single-family homes on the west side of San Francisco, where I own property. As a result, I felt wealthier. Finally, the stock market continued to do well.
The Need And Desire To Work Waned
All of these positive financial events made me question why I was spending 20+ hours a week consulting when I could be spending more time with my family and enjoying life.
But even in a bear market, I'd question spending time working for money when my investments would easily lose 2 – 5X the amount I'd earn in a year.
Back in 2012, I reached my minimum investment threshold amount where work became optional. Today, I'm far wealthier, which means I have an even lower tolerance for work that's not ideal.
Takes Effort To Find The Best Work Fit
I still would have liked to continue earning my consulting income if the work arrangement was awesome. But it was not, so I chose happiness over money. I have this option because I have diligently saved and invested most of my income since 1999.
Instead of consulting for a seed-stage startup, I'm probably better suited to consult at a Series B or later stage startup. These startups have usually been around for 5+ years and have more infrastructure in place. The CEOs also have more experience managing a team.
I wish the startup that hired me the best. They are hard workers and good people with a high-potential product. I appreciate the opportunity they gave me. I'm just sorry things didn't work out for both sides. But I'm glad I went through this experience because I now know better what to look for.
Summary of Going Back to Work and Failing to Last
- Don't be too proud to go back to work in any capacity to provide for your family. It is your duty and an honor to protect them.
- Expect constant meetings, management feedback, and changes in responsibility. Work is work, not play, no matter how hard a company tries to make it fun.
- Not feeling heard or appreciated by your colleagues is hard. But remind yourself that as long as you are getting fairly paid, try not to feel disappointed in others' lack of appreciation for your work.
- The more you love or need money, the easier it will be to take criticism and choose work over spending time with your children and vice versa.
- Suggest a different arrangement in terms of work hours, pay, and responsibilities if you want to stay.
- Finding the right company at the right stage of its maturity is extremely important for fit and longevity. Working at a startup is not for everyone.
- If you just can't make things work after trying, it's best for both sides if you move on. Don't settle for a suboptimal situation if you're going to spend so much time working.
As for what's next, here's my plan: Instead of looking for work again before my daughter goes to school full-time, I'm going to wait until after she starts and then make a decision. This way, I'll get a better idea of my free time.
In terms of paying for the gap between our passive investment income and our expenses, I have online income and book advance installments that will carry us through. In a worst-case financial scenario, I will try to sell a rental property to come up with liquidity. Let’s just hope a bear market doesn’t come to pass.
Have you ever had difficulty adjusting to a new company? If so, how did you manage to adapt? What's the shortest amount of time you've worked for a company? How can we do a better job of determining whether a new work opportunity is the right fit to reduce wasting time and energy?
Recommendation For Those Who Want To Quit Their Jobs
Hate your job? Pick up a copy of “How To Engineer Your Layoff” that teaches you how to break free with money in your pocket. Both my wife and I negotiated severance packages, which enabled us to live the lives we truly wanted.
My book has been updated six times since 2012 with new information and strategies. Use the code “saveten” to save $10 at checkout. It's way cheaper and more insightful than hiring an employment lawyer for $600/hour.
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I Went Back To Work And Only Lasted Four Months is a Financial Samurai original post. All rights reserved.
I think you may be WAY over-budgeting for the cost of university in the USA.
In 2023, the average college tuition cost at a public university was $10,662 USD and $42,162 USD at a private college. For out-of-state students (including international students), the average cost is $23,630 USD (U.S. News & World Report). [https://shorelight.com/student-stories/what-do-fees-mean-at-us-universities/]
Depending on what your children wish to go into, a university education may not even be required because education is widely available online and through Google career certificates.
Could be. But I suggest also looking up some public and private colleges right now and seeing what the all-in cost is per year. Then model out what it will cost in the future using historical growth rates of 5-6% a year.
But one of the greatest hacks for Americans is taking advantage of Canada for education. So there is always a way to save money!
I was given a choice between 3 universities. All of them had “live for free” at home or with grandparents. That cut the cost down to tuition and books.
Oh man, it’s nice to save money. But boy, those four years in college were the most fun I’ve had in my life. Truly a blast!
What is it that you do now? And how many kids do you have?
I still had a blast while saving money. They are not mutually exclusive.
I work still remotely (fewer hours) while traveling and no kids here.
Cool. I think you’ll enjoy this post:
https://www.financialsamurai.com/how-to-get-girls-if-you-live-at-home-with-mom-dad/
Thanks but I don’t live at home with mom and dad and I am not interested in dating women either ;-)
I really enjoyed this post, as a middle-aged father who stopped working in 2021 and has deliberately not returned to the workforce since (very fortunate circumstances in general, plus we realized that our family of four can live off of a combination of single-traditional-income plus passive income…. for a few years). These last few years as mostly a stay-at-home dad have been amazing, and your article correctly (in my opinion) pointed out the potential regret of not spending enough time and building meaningful relationships with your children FAR OUTWEIGHING the potential regrets of not working enough (?) or achieving a certain salary, title, or other career related milestones that our society tells us are important but for most don’t bring true happiness. I also really appreciated your early points about 1) a decreased tolerance for working for and with other people as you age and earn wealth, and 2) accepting a new job is a giant leap of faith rather than certainty of a “good fit”. These are primary reasons why I haven’t gone back to traditional work. I’m starting to generate more passive income (through real estate) in the meantime, and if there comes a greater need for me to earn significantly more money in the future, I am a lot more likely to start something on my own (despite having no entrepreneurial experience or tendencies) than to go back to a corporate environment where I spent 17 years.
The problem of feedback, genuine interaction with readers plus the editorial freedom are hard to replace once you’ve run a successful blog.
Interesting article, and sorry it didn’t go to plan. I thought your comment about the podcast was odd – a comment may take a minute, but how long was the podcast? If I am up to my neck in work at a startup, maybe I don9t have the time to listen to it?
A pet hate of mine at work is having to second-check other people’s work in SAP, as they expect me to catch their errors rather than get it right first time. Maybe the CEO didn’t expect to have to do this with the newsletter links? He seemed to raise it in a civil enough way – other businesses would be a lot blunter, I’m sure
Interested to hear what the especially disrespectful comment was.
No worries. I totally get it if a small team of employees aren’t willing to support or listen to a podcast where their CEO is on for 30 min and rate it. I realize that everybody is too busy doing their own thing. I am probably the oddball in reviewing their podcast.
I think you might be different in double checking, because if you took it upon yourself to double check everything and change the content for months, I don’t think you would one day say “how come you didn’t include so-and-so.” But maybe you would? It was just the straw that broke the camel’s back. I didn’t complain, I just said it wasn’t working out and decided to part ways. Better to take action then to complain and be unhappy.
How long have you been working so far and how much longer do you plan to work? Always good to know the background of commenters. Thanks.
Ahh, the CEO was on it – a detail worth adding to the original article.
Maybe the CEO was under more time pressure and hence changed tack? Maybe argued with his partner just beforehand, stubbed his toe, received bad news and was distracted? It bugs me when links don’t work as I think that if they are included, they should work – if they don’t, it comes across as slapdash. That doesn’t sound like you (based in a few years of reading the blog) but maybe that’s what he was thinking. People do thoughtless things for trivial reasons – I guess my rambling point is, I doubt he meant deliberate offence by the comment.
Working for 30 years at jobs in technical/quality that I wouldn’t dignify with “mid level”. If I can last another 5 years it’d be good. Probably NOT at the current company – a mid size USA chemical business, in a UK location – as the older I get, the more full of sh!t senior managers get, and I enjoy poking the bear.
“But something also disrespectful happened, which made me decide to stop going in weekly after a month. Now that I think deeper, this disrespectful event permanently changed my enthusiasm for consulting with the company. I’ll share the story in an upcoming article if you’re interested.“
In your good time, I would like to read more about this. Their loss…..
Me too!
Ditto!
Great post. Was the disrespectful incident immediately addressed, with your firmest principles and boundaries? I felt too, as a reader, that “Will do” may not have been your most assertive communication back to an aloof disrespectful text for which a quick phone call would have brought you together. This kind of virtual slapping behaviour is weirdly common and destructive in a modern work environment in which emotional intelligence is repeatedly dissolving business value and taking human spirit with it. If it was a public company, I’d short the stock, because in the long run, small things always become big things.
((HUGS))
Thank you for such a vulnerable post! And no I’m not surprised at all that being your own boss for so many years, controlling your own schedule, and playing such a huge role in your children’s lives has made you resistant to the frustrating realities of a “regular” job.
I too have worked at startups, and they are chaotic and schedules change on a dime. I don’t think at this point in my life (mid 50s and net worth of $5 million) that I would go back to that world. I still work full-time for a large company, but my boss is largely hands-off because we’ve worked together for years and we understand what each other needs, and I respect his boss (the CEO) enormously. If my boss, or the CEO, change I think all bets are off, depending on who replaces them. I want to work, but I don’t NEED to work any more, and like you I’m no longer needy enough to put up with a work environment that doesn’t work for me.
Sounds like you’ve learned a lot, and you have a solid plan once your daughter is in school full time. Best wishes!
Hey Sam,
I just wanted to reach out to thank you for this article about leaving your new job.
I have a somewhat similar story to share – though there are some significant differences. First, I’m considerably older than you (i.e., 62) so I’m nearing retirement anyway – but after having been laid off from my job in 2021, I did some consulting for a P.E. firm that was very enjoyable, studied to become a psychedelic facilitator (really… psychedelics are actually quite effective in treating trauma), and did some random other consulting for the next year-and-a-half. Every time we lost out on an acquisition, I was secretly happy since I wasn’t really that interested in going full-time again. And then it happened.
We succeeded. And now I took a C-suite position with the new company as was expected. But as time has gone on, I find that my heart just isn’t in it anymore. And literally today, my wife and I were discussing this and what I should do (e.g., go part-time, consult, leave, etc). I’m still not 100% sure, but I know that I’m done with full-time work for real this time. It’s just what comes next that’s the question.
And then I read your post. Talk about synchronicity. Best of luck with your decision, Sam and thank you for your posts.
Regards,
Paul
I went back to work off after 6 years of staying home taking care of 3 young kids. The first year at work was challenging in every aspect but it was still a vacation compared to the 6 exhausting years at home with kids when it was a 24/7 job. My boss wasn’t ideal but I treated him like a customer and customers were always right! I gained his trust and he gave me two people the second years to manage and delegate work to so it’s getting better. I still have more work than I could handle but I suck it up and find ways to be more efficient . I have no intent to leave and can see a better professional future in the horizon.
Hello Sam, Good article as always !
I understand the fear linked miss of money, but after 12 years, come back in a work it’s very complex, never ill that ! Honnestly I’ve a ENTJ personnality, so the emotion positives or negatives (proud or not) of other person (colleagues) on my work haven’t that few impact on me, all my life it’s the permanently critics of my family and friends who was a booster, more they belittled me more to give me of strength.
Sure, we haven’t lived the same life and had the same family and entourages.
But at least you had courage and tried the experience.
Bravo for that !
I keep coming back to the fact that you “recruited” your wife to do part of your job. WTF, man?
Crazy, right!? It was a solution to try to capture the voice the CEO wanted, which I couldn’t quite do after 2 months.
My wife spoke to the CEO and had dinner with her multiple times as well to work together and find a solution. She even consulted on how to start their podcast for free.
So in reality, the company had a two-for-one special. And part of the reason why was due to the amount of work that one’s more than my part-time hours could finish. And that’s unsustainable.
Always try to look for solutions to difficult problems.
That’s unfortunate. As someone living paycheck to paycheck, you’ll struggle with next month’s bills
You’re probably right. But I have to struggle in order to provide for my family based on the choices that I’ve made. As a result, I need to learn to appreciate the struggle and fight on.
Thank you for sharing all of this.
Your candidness is one of the reasons that I’m a long-time reader.
This article was inspirational and really stirred my emotions (positive and negative).
I have worked 65 days straight and have been on-call 24/7 as well because two of my former colleagues resigned in the past several months and the third went on maternity leave.
The owners of the company and CEO dragged their feet on posting an add for addition help. They told me at the last minute that their plan was to have me just suck it up and get absolutely buried so they could save money (for themselves) by not hiring another medical provider.
I am the keystone at my company and without me they would not have been able to continue to operate and would have gone out of business. Yet, my employer has not once thanked me for the sacrifice I have made for the company.
I had to miss out on two family vacations this summer (a week at mountain town in Colorado and then a week in the Bahamas). It absolutely killed me to see the pictures of my family without me on vacation.
When my family has been home, I have been too tired and irritated to be present with them (and it’s been eating me up inside).
My children are 9 and 7 and these years are precious and I missed out on amazing family memories. After reading this article, and the comment section below, well, it was motivational to say the least and the final nudge I needed.
Although youngish (47), I am FI. I am now determined to go to work tomorrow and quit as soon as I complete morning rounds on my patients and finish my morning coffee. Hello FIRE, here I come! Thank you Sam!
Thank you for sharing. Sorry you have been so buried with work. That’s not fair and the owners are playing with fire given they are already down two people down.
I would highly highly recommend you try to negotiate a Severance instead of quit. You are in the prime position to ask for anything you want. If you are the key, then you leaving screws your employer, and they will do anything to keep you or help you transition out.
I know this is an emotional and exhausting time. But you have to think strategically for the sake of your family. Maximize your situation and strategize forward!
I understand your stance. However, it’s a little more complicated than that. The CEO is morally corrupt. Just the other day, behind my back, he instructed non-medical staff to disobey a direct medical order and allowed a critically ill patient (in respect to their mental health state) to leave the facility in her vehicle with the intent she would return later that evening. That act jeopardized the life of the patient and the wellbeing of the general public. If there would have been a bad outcome, the company’s ability to remain open and my medical license would have been on the line as well. It is a preposterous situation to say the least. It has taken a couple days to speak with the nursing staff and ancillary staff to find out the sequence of events and all the bad actors that were involved. Tomorrow I will present the information I have gathered to the owners and demand all involved to be fired. However, I have little faith that there will be justice as the CEO, the Head of HR, and the owners all family members, and the remaining staff involved are friends of that family. So I anticipate after making rounds and finishing my coffee, I will be disappointed with the results of the meeting with the owners, and enter the world of FIRE immediately. I would rather be poorer and have my self-respect (and medical license) intact than to work on a slow exit to help with a transition. No amount of money is worth sticking around to work for a company like that.
Hello Financial Samurai! This is the first blog post I’m reading and I happened to come across this comment. Does the strategy outlined in your book work for federal government employees? (considering we are not a Fortune 500 company and are paid by American taxpayers). I’ve been working my job for 10 years and am beyond ready for a reprieve!
Hi Ty, welcome. Financial Samurai began in 2009 and is one of the top personal finance sites today.
My strategies in my book are relevant bc every employee has a boss who can help with the employee’s transition, whatever that might be.
-Sam
Hello Sam. thanks for the welcome. Okay I will consider getting your book. I just typically don’t hear of severance packages for fed govt employees unless it’s something SUPER egregious.
Parent guilt represent.
I always end up feeling guilty when I can’t muster enough energy to be fully present with my kids. The crushing feeling of knowing I could’ve done better to enrich their day instead of brushing them off is devastating. Especially at night time when I see them sleeping peacefully…
I do much better muscling through fatigue now to savor more moments, but I have also realized that I shouldn’t count the moments of failure. It’s just a part of life. Without it, I may have taken things for granted.
Great article. Totally get why it wasn’t right for you. Maybe consider a part time consulting gig if you can find the right match. That’s what I do. Have a large client and meet with the CEO to discuss issues they are having and render my opinion. I’m not responsible for implementation and they can take or leave my recommendations. No prep work. Just giving suggestions based on my prior experience. Pays a lot although I don’t need the $. Keeps me a little engaged after a long career and now retirement. Am sure plenty of companies could use your expertise. Good luck!
Hi Sam, it sounds like that job sucked. The environment you described wouldn’t have worked for me either. I think you made the right choice! Good luck with finding another job if that’s what you decide to do.
I think you partly just ran into the annoying problem with small start ups. Everyone is over worked and they treat their employees like garbage. They get away with it though because the employees have equity and hope to get rich some day. They also offer free food and office perks. You have to really be into it to want to work there.
Do you wish you had never quit? I don’t think it would be easy to leave work for a few years then come back to all the bull shit.
Maybe you are right.
I wish I continued to work to meet my goal of lasting for at least one year. It doesn’t feel good when things don’t work out as planned. But that’s life.
These transitions are NOT easy, but that’s what makes them a fun challenge.
I wish I was given more freedom to plan, create, and execute, because I know exactly what is needed for growth.
Oh well. Better luck next time!
So many meetings and messages and the anxiety of it is my life too at a big company. But it goes up and down and they treat me very well. At my last job though, I had disrespect that I still remember almost 9 years later. They were forcing me to move north from Florida, which I Ioved (and made the huge mistake of selling that house for a big profit with all closing costs paid by my employer when I should have rented it out). I remember telling my boss I heard something the day before. She got so mad at me that I didn’t tell my new boss who had started 2 days before and had not met me yet. It was the holidays and l agonized a lot about it.
I stayed 3 1/2 more years, got some great accomplishments, and got to my current job that I love.
“ made the huge mistake of selling that house for a big profit with all closing costs paid by my employer when I should have rented it out”
Remind me again what are you selling for a huge profit was a big mistake?
Yes, happy to share again (since I am still conflicted about it).
In 2016, I sold my house in South Florida for $451,000 and got $6,500 taxable bonus from my employer because the offer had come within 60 days. My employer paid all the closing costs and the 6% real estate fee since it was company relocation. I moved because the company said I had to move or lose my job.
I had bought the house as a short sale 2 years earlier, also on a company relocation. 5/1 ARM at 3%. So the company also paid all the closing costs when I bought for $419,000. The owners were still living in it, so the house was in good shape. So I made $32,000 in the house, tax free, and got a $6,500 taxable bonus from my employer.
Sometimes I regret selling it instead of renting it. However, I had interviewed property managers, but wasn’t happy and calculated I’d only make $200 – $300 / month. The real estate agent first made me think I’d sell if for $475,000 though her paperwork showed $456,000 and she was terrible at returning calls when the first offers fell through. Also, my old boss in 2015 recommended selling it, saying it would be too hard to manage.
Part of the reason I also sold is I found the house of my dreams in the north east, for $450,000. I’m typing this from there right now (8 1/2 years after I bought it). As I have mentioned previously, I bought it at 5/1 3%, then had 2 5/8%, then 3%, then 5%, then 7% this April and then paid it off. Also, while I loved my Florida house, I do believe my current house is a better house and better community for my family than the Florida house.
That old Florida house has now has a value of more than $800k; my current house has risen to the high $600s, though I finished my basement (900 sq ft) so likely more. My old boss, when I saw him again in 2022 and 2024 reiterated that it’s good I sold the Florida house. He noted that in Florida, if I was renting it out, they could increase the property taxes with rise in value, and property insurance has gone up a lot too. He said that for the price of one year’s property taxes in Florida, I could take a very, very nice vacation in Florida, and not have to worry about renters, maintenance, or anything else.
So that’s why I sometimes feel like I made a mistake, even though I made a lot of money by selling my Florida short sale 2 years after buying it, with my employer paying the closing costs and commissions on both the buy and the sale.
I had a friend who often said about this subject “That’s why they call it work.”
What a great article! After reading your description of the work environment, I suspect the two big issues that drove you away were rooted in micromanagement and poor efficiency from your colleagues. Micromanagement can only be avoided by either finding a good boss (rare), or taking only jobs as a top technical leader where the executive team/CEO doesn’t have the requisite skills to interfere. My career is in engineering so it’s pretty easy to shoot down a higher level micromanager with logical reasoning about a number technical details that only the very focused would have time to think through (i.e. skilled individual contributors). Without the micromanagement, my “voice” is retained as the working product ends up belonging to my team and myself. Your role as described is certainly a “technical” leader role that should have afforded you the same benefits, but you just had the wrong CEO. Did you show the CEO that his writing was more poorly received or that he edited his own edits? Perhaps he would have allowed some blind tests to show who was the better writer and then relaxed on his micromanagement after seeing the “data”.
The other big issue is that the CEO and your coworkers lack efficiency due to poor communication (meetings/slack) and planning skills (schedules changing). For example, too many meetings is common problem and much of the corporate world lacks the ability to run efficient meetings. Over the years, I have developed some coping strategies, which are now just habits. For example, I block out my calendar from 6 to 8:30 am, lunch, and some random time at the end of the day. If someone requests a meeting, I decline and ask them to look for an open spot on my calendar. If a meeting has no agenda, I will request one before accepting. All of this results in a scarcity of others getting my time, which forces very efficient meetings when they do. Moreover, after the meeting, I will ask the meeting organizer for notes, which I primarily ask as a small tax on the organizer lest they become too frivolous with scheduling meetings. With slack/teams/emails, I am never the first to respond in a group, and it pays to wait for a discussion to sort itself out. In fact, there are now some AI tools which will summarize the whole conversation, and suggest cogent responses. On the planning side, experienced coworkers should be able to adhere to weekly schedule, and if not, they need to be shoehorned into a rigorous process that ensure timely results. Often, I will create those processes if needed. Unfortunately, the poor work habits of your coworkers ended up costing your personal time with your family.
In any case, the problems you described at your startup suggest a poorly functioning company, unlikely to succeed anytime soon. Best to cut your losses early and find a better opportunity (or just ride out the new bull market).
I definitely wasn’t used to meetings every day. Where are you had to go around and hear what everybody was up to and then share what you were up to. It’s pretty good if it lasts for 10 minutes or less given the team was small. But if you are part time, I felt pressure to dial in every day, which is on me. And this pressure ended up distracting me on my days off with my family. It’s hard to just tell them you won’t be going on even though they will say it’s OK.
Yes, being micromanaged is difficult. It’s truly not an enjoyable experience, and I feel bad for any experienced adult employee who gets this type of management.
I didn’t mention it in my post, but there was another person who was hired to do content before I came, and she only lasted four months too. But my production was literally 10 times greater than hers. And yet, things still didn’t work out.
Sam,
Thank you for your posts through the years. I was thinking about the new ADU (Accessory Dwelling Unit) laws in California and other states that allow a 2nd and 3rd unit on a SFR lot despite local zoning ordinances. These laws were enacted to combat the housing shortage. I believe these other units can then be rented or split into separate lots and sold, perhaps with some restrictions. You may become hugely unpopular with your neighbors, but this seems like a stealth way to build a real estate portfolio. Perhaps one of your in depth posts on this is in order. I would love to hear your thoughts!
Hey Sam
This is a first time post for me, but your article really resonated. I wish you had written it 15 years ago.
As a person who continued to work at consulting gigs during my children’s formative years and not being fully present because I was stressed/or like you, just wanted to do a good job, I want to say you made the right choice. My kids are now 14 and 16, and there’s a saying you only have 18 summers with your kids – well, it’s actually 12-13 (camp trips, internships, etc.). I look back and wished I hadn’t wasted time/stress/energy worrying about money but instead truly being present for them!
Congrats on making the right decision.
PS I wouldn’t worry so much about college/bills. Start the 529 account now, and it will grow in time. And things do work out…I wish I had listened to my husband, who had told me not to stress. He was right.
Hi Patricia,
Thanks for sharing your experience. Yeah, it’s tough to do “half work,” as my natural tendency is to give everything I’ve got, partly due to pride, and partly due to not wanting to experience regret.
Your husband sounds like a chill guy. Is he doing well in his career? As the mom, maybe it’s just harder not to worry and stress about work and childcare? I dunno. But the good thing with you is that you did both, stayed relevant, made some money, and still got to spend time with your kids. Plus, you still have 2-4 years left with them!
I hope things do work out with paying for college. I had an epiphany on when to stop saving in a 529 plan because we’ve been aggressively saving for two since our kids were born.
Sam — Good on you for taking a chance, tho I don’t think you needed to do so, financially or otherwise. ;-)
This said, when you wrote: “Then, one afternoon, I got a stern Slack message from the CEO saying something like, ‘You didn’t include the proper links to the articles. Be more careful next time as I expect you to have the newsletter ready to publish when I review it.’ This is a totally normal comment.”, what did you mean by “This is a totally normal comment.”?
I just mean that it’s a normal directive to ask a subordinate. But it was also uncharacteristic b/c I was asked to put together the newsletter last minute after working on a bunch of posts. And instead of going in with the usual collaborative tone, where the CEO seemed eager to do a lot of the editing, their tone changed.
So unfortunately, it was the last straw for me as I didn’t want to feel bad for working so hard.
Got it. I’ll respectfully push back on you. I believe that the substance of the comment was “normal” and acceptable. That said, the delivery as you relate it is, IMHO, the mark of an immature and/or ineffective leader and should not be considered normal or normalized. Having employees feel a little fear and anxiety is ok . . . to a point. The point being where the employees don’t want to disappoint their superiors. In other words, internal drive.
It crosses that point when they just think the superior is a jerk (I have another word I’d like to use here, but this is a family blog after all). Once that point is reached, the employee’s loyalty and morale probably is lost, and they’re likely not going to give it their best every day. At the least they likely want to leave, and at worst they’re itching to do so.
Sadly, it’s comments delivered in the way the comment you called out that were among the top reasons I wanted to FIRE. I could and can take pointed comments and criticism. What I ultimately refused to stand for was comments delivered in such a jerky (read another word) way. I voted with my feet. Had all my superiors been nice, constructive, and collaborative, and never jerky, I might still be happily working in my old field (even if FI).
Every time someone gets away with the type of nonsense the CEO did, he or she is emboldened and has all the more reason to believe it’s not only a normal way to deliver a comment, but acceptable. To me, that’s a shame (full disclosure, I put up with it for a long time, so I was as guilty of this as anyone). I’m glad you considered it the last straw. I only wish your counteraction would have been something that would have had a (more) adverse consequence for the company so as to maybe have them learn a lesson.
I see. I think the CEO probably thought their comment was fine too and probably just rushed it out over Slack with their busy schedule. I could have just sucked it up after working hard on the last minute newsletter request. But I decided to speak up.
I don’t want to do anything vindictive as they are good people. It takes two to make a relationship work.
But wait until you read the follow up story about how a disrespectful incident really made me not want to come into the office again.
That’s awesome Sam. I went back to work and lasted 2 days. They gave me a decent salary and the ability to WFH but when I thought about my kids I said no thank you. I’ll figure out another way. I learned about Pledge Asset Accounts from one of your blogs and decided to use that in the meantime. Sure I have accumulated margin but its ok. I figured things out and other investment opportunities came up that will eventually help me offset my expenses and hopefully start reducing some margin as well. Well worth it imo.
Must be a relatively young CEO, especially since it’s a first time CEO.
Weird to not let you cook more independently. The ROI on you organically mentioning the company you work for, whose product you enjoy using in relevant posts, would pay back 10X in returns through direct leads and greater brand awareness.
Glad you explored and decided it wasn’t for you. Thanks for sharing.
I thought the same Andy. As someone who works in digital marketing and has sold a company I cannot believe the CEO didn’t see the potential ROI the link-up would provide and just give him free reign to produce the content he desired.
To persuade Sam to go work for the company and actually get him involved was huge for them. To replace the organic reach he could provide is going to cost a fortune in paid marketing.
Madness.
CEO sounds like a complete nightmare and whoever is funding this startup id be looking to pull my money out asap. It’s destined to fail.
Thanks guys, but I wouldn’t go that far. The CEO and the team are great people and extremely hard workers. Yes, it would have been nice to weave their product into so many salient posts of mine over the years. But it was just not meant to be.
I was just surprised the CEO wanted to end things so quickly after I mentioned things weren’t working out. They might have picked up some recommendation of “hire quickly, fire fast” type of mantra in startup Silicon Valley land and didn’t thoroughly think things through.
But that’s a good lesson for me to if I decide to hop back in. Everybody is quitting quickly and firing quickly. Gotta look out for yourself I guess.