We spend a hell of a lot of time talking about early retirement. Things like how to get there. What we’ll do once we get there. How awesome it is to actually be there…things like that. But, how about we change things up today and talk about something different. Like, pretty much the complete opposite. 

Under what circumstances would you NOT retire early? What would make you suddenly change your mind? Or, maybe you never would have considered early retirement to begin with if something worked out differently.

What would make me NOT retire early?

For me, it’s simple. Early retirement is my way of achieving happiness. Even doing work that I generally enjoy (information technology), I certainly didn’t enjoy the jobiness of it all. The performance reviews. The arbitrary requirements. The insane schedules. No thanks, that stuff just sucked.

I quit working in corporate American because it fundamentally made me unhappy.

But, what if it did make me happy? If I could honestly tell myself that I’m happy with my place working a full-time job, I wouldn’t retire early. I’d work toward financial independence, but early retirement would probably not be in the plans. After all, there’s nothing to escape from if I’m having the time of my life.

Why not keep working a job that I thoroughly enjoy and put all that beautiful cash flow to good use? Like investments in my future. Or charity.

If corporate America made me happy, I’d still be working.

I asked my wife this same question, and here’s her response:

As many of you know, I tried to retire early but got talked into taking a sabbatical and going back for another 6 months. The major reason for this was loyalty and the fact that the team I work with is an awesome group of people. I also don’t hate my job. In fact, I would NOT retire early if I could continue doing what I’m doing, with the people I’m doing it with, but have the freedom to choose my schedule (I can’t). In my line of work, I am trapped in a windowless building for 9+ hours a day. There is no way to work from home, let alone work remotely and travel in our Airstream. If that was an option, I’d take it!

So if I was working a job I enjoyed, with people I liked and respected, and had the freedom to work remotely/set my own schedule I would not retire early and would instead be part of the Fat FIRE community.

Not to mention that if Courtney worked full-time, our YouTube channel would probably suffer hardcore!

From the personal finance blogosphere

To offer up different perspectives, I asked around the personal finance blogosphere for insight into what would make bloggers keep working instead of retiring early. Here’s what they had to say.

Michael – FinanciallyAlert.com

I think one circumstance where I wouldn’t retire is if I were running a multi-million dollar company that was well aged. By well aged, I mean that it already has enough defined processes that generate a healthy profit margin. It would also have a strong enough team I could rely on that didn’t require my presence. As the owner, I’d be responsible for long-term strategic decisions and team building. I’d also have the freedom to direct profits however I saw fit which could give me some additional tax benefits personally.

This scenario would be enticing for me because I’d have enough freedom built into my “job” as the owner, but enough unknowns to keep it interesting. I enjoy any entrepreneurial project that has the potential to grow exponentially.

[From Steve: Pretty kickin’. Truth be told that if I had a high-income company that I worked my ass off to produce, I’d probably have an extremely tough time severing ties too.]

Michael Dinich – MichaelDinich.net

I would not retire early because of my children. My kids Anna and Gabe are 10 and 8 respectively, and I dream that they will take over my firm (After they get PhDs and win Nobel prizes, of course!).

If they join the company, I would want to help and support them, so I would keep working. Luckily, I love what I do so I’m in no rush to “retire.” I do want to become self-sufficient and have enough guaranteed income I don’t have to work, but no goals to actually stop working.

If my children decided not to join the company, I would probably just scale back my office hours. I feel a sense of obligation to my clients and I couldn’t turn them over to someone and just walk away.

Aaron – PersonalFinanceForBeginners.com

An entrepreneurial pursuit would be the only way to persuade me NOT to retire early. That’s not to say there aren’t non-financial benefits to working corporate job. It’s just that none of those satisfying aspects of work – creating new things, learning and applying skills, building relationships, and being part of something larger than one’s self – are exclusive to an office setting.

I’d consider working indefinitely if I owned a scalable lifestyle business – one that allowed me to set my own hours, outsource work I don’t enjoy and automate processes to optimally leverage my time. I’d need to see an opportunity for ongoing growth… I assume that even “easy” money becomes drudge work without variety and new challenges (admittedly a mighty fine problem to have).

[Note from Steve: I absolutely love this quote: “It’s just that none of those satisfying aspects of work – … – are exclusive to an office setting”. I couldn’t agree more and wish that more people would realize that life outside of an office can offer the same level of satisfaction as inside.]

Financial Journeyman – TheFinancialJourneyman.com

The only reason would be due to money. There are two financial scenarios that I can think of. The first would be that I did not have enough money saved that I felt comfortable with to call it a career. For me, that number is around 40 years of living expenses in savings. I am looking at a 2% drawdown rate. I am more conservative than the masses or what the academics suggest as being safe. The second scenario would be that if I put in my notice and they offered me a salary that is far more than what the market states that my position is worth. I would stick it out for a few more years if I was offered a 50% raise.

[Note from Steve: Understandable! Money talks, and working a few extra years while earning a stupid big salary has “wisdom” written all over it.]

Miguel – RichMiser.com

I don’t know that I would ever retire completely from the practice of law because it’s a way to leave a legacy beyond my lifetime. Primarily, it rests in changing clients’ lives for the better, and in being an advocate in cases that go into law books. It makes me feel that, in that little corner of the universe (the legal world), my name will always be somewhere.

With financial independence, I’d definitely scale back my hours, but I don’t think I’d fully quit practicing law.

John – ESIMoney.com

Here are some times I would probably not retire early:

  1. If my job provided some vital and/or unbelievably expensive benefit that I could not find elsewhere. Many people with medical conditions probably face this sort of issue.
  2. If I LOVED my job! Why retire if you’re having fun?
  3. If I was a moron who was already FI and yet did not run the numbers to know it. (Don’t ask how I know this one.)
  4. If I had to choose between working and living in an Airstream. LOL!

[Note from Steve: That last one was not funny, John!  😉]

John – FrugalRules.com

If I, or someone in my family, relied on [my healthcare] coverage, I’d put off early retirement to a more suitable timeframe relative to their needs and specific situation.

I’d also add that I would not retire early if our kids were not yet in college. Assuming they go, we’ll be helping them to a certain extent and would not want that to be too much of a burden financially for my wife and me. We face that situation a bit now as we started a family later than we wanted so our youngest will be thinking of college in my early 50s. That works out well with our timing as I think my wife would have serious issues if I were to be retired sooner, lol.

Derek – LifeAndMyFinance.com

  1. My wife’s love of my work’s medical insurance. I’m not sure if she doesn’t realize that we could buy our own medical insurance if I didn’t work a job…but every time I ponder working for myself in some capacity, she flies off the handle and starts asking me what we’ll do if something happens to the kids and we don’t have my corporate insurance…
  2. I enjoy the people I work with. If I were to retire tomorrow, I would lose ties with a few good friends at work. Sure, we could always get together outside of work, but unless you’re super intentional, the friendship would likely fizzle and would leave me having to make new friends.
  3. If I ever thought my passive or side income could drop dramatically (or that I could lose it all). There’s a security in those bi-weekly paychecks.
  4. If I thought I could make it to the executive level. At my work, when you become an executive, the bonuses are crazy and if there’s a chance that you could earn your salary for life. Those two factors might be worth sticking around for a few more years.

Flawed – TheFlawedConsumer.com

For me, I think being my own worst enemy would stop me from retiring early.

I am a risk adverse planner who considers every possible scenario and plans for the worst case. As a result, I’m not actually sure that even if I was able to get the figures sorted and become financially independent, that I would be able to bring myself to the edge of the ledge and step off into the unknown world of early retirement. I could see myself getting to the ledge and then taking a step backward when I think about the statistical likelihood that at least one of us will get cancer in our lifetime. Taking another step backward when I think about the possibility of something major happening to my house that’s not covered by insurance because I’ve missed seeing it in the product disclosure statement. And, so on and so forth.

As a result, I think the only circumstance that would hold me back from retiring early, is having the time to truly think about the prospect!

The Dude From – FIIntrovert.com

I wouldn’t retire if I didn’t have to be at a desk or tied to a computer just to be available in case someone needs me. I can feel my hips tightening throughout the day and sitting here in front of this screen is just so…confining. If I could live in a lower cost area near mountains and lakes and woods where I could plan out when I needed to be on calls/in meetings but the rest of the time have the freedom to do work whenever I wanted without having to be at a desk in daylight hours, I would probably keep working in the line of work I am doing now.

Busy Mom – CountdownToTranquility.com

The only reason I would not retire even if I have enough money is if I love whatever I am doing very much. I will also need the flexibility to work whenever I want to.

If the weather is great, I want to go for a walk. If I don’t feel like working one day, and I want to work more the next day, I want to do exactly that. Maybe if I am paid by the hour, or I start something myself? Can’t see it happening otherwise.

My main concern now is that I spend most of my day at work, and I don’t enjoy it enough. Maybe I will be happy if I could just work half the time? I don’t know.

MoneyLogue – MoneyLogue.com

The one and the only reason why I won’t retire early is if the company I am working for finally recognizes how great of an employee I am and decides to offer me a seat on the board of directors. Will they do it? Probably not in my wildest dream.

What about you folks? Under what circumstances would you never consider retiring early?

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