I Could Have Been FI by Now …

Have you ever looked back and thought, “If I didn’t make that dumb-ass financial mistake years ago, I would have had XXX more money right now!! What was I thinking!?” 🤦‍♂️

I came to a similar realization recently… If I’d never left my sales job a few years ago, there’s a fair chance my wife and I would have reached FI this year. 🤯 Crazy! I could have been “retired” right now, at age 36…

But instead, we’re still many years away from financial independence.

For those of you who don’t know, in early 2018 my wife and I left our jobs to begin a 1 year sabbatical. It somehow turned into 2 years off for me, and since then I’ve only returned to part-time work, earning less than 1/5th of my prior salary. We are now on the Coast FI train, intentionally slowing down our journey to FI.

If I’m being honest, it feels really shitty thinking about how much money we’d have in the bank if I’d just continued working. Part of me is kicking myself for not taking full advantage of high-income-earning years.

But, the other half of me is at peace with it all. I’ve accomplished some cool stuff and grown a lot as a person the past 3-4 years. My lifestyle is already much like a retired person’s. If I could go back and change it all, I’m not sure that I would.

I’m still processing all the thoughts and feelings on this, so bear with me if some of this post flip-flops around a bit. There’s a bunch of things to consider …

Regarding the Money …

OK, so, if I never left my old job and kept earning money until today, my guess is we’d have an additional $500-700k saved for retirement. Maybe more. The reason I can’t calculate an exact savings number is because 50% of my salary was commission-based. Who knows, maybe if I had a blowout sales year I could have saved an extra 1M+ over the past 3-4 years. Very possible and crazy to think about!  (It’s also possible I could have been fired or laid off during covid – you never know).

But, would having $1M more in the bank really change much for me right now? Would I really feel more free, confident, or happy than I am right now? I don’t know. 🤷‍♂️

Growing up I’ve always had this recurring thought… “If I just had XXX amount of money, I would finally feel good about things.” In my early 20s that number was like $100k, then it grew to $500k, then $1M, and beyond… Somewhere along the way I realized this might be an unquenchable thirst. I am trying to chase feelings (freedom, confidence, happiness) that aren’t actually tied to how much money I have in the bank.

In fact, one of my favorite posts from Mr. Money Mustache is called Money and Confidence are Interchangeable. Here’s an illustration from the post…


This blog post came out right around the time I was quitting my job, and it helped a lot with my mindset shift. My biggest takeaway was that more money doesn’t actually give me a whole lot more confidence in life. In fact, I was noticing the opposite. As my savings pile grew, I became more adamant on needing my number to be bigger and bigger.

Would it be nice to have an extra $1M in my retirement accounts right now? YES!!!!

But would it realistically change what I’m capable of in this world? NO!!!

Regarding Personal Growth …

Anyone who’s taken a long sabbatical can probably confirm this:  You experience rapid change as a person during time away from work. 

It’s like cramming 10 years of living into just 12 months.

Without work interfering with everyday decisions, you start to question things… EVERY thing, in all aspects of your life. Personal development, reflection, your relationships, travel, career evaluation, emotional progress — you name it, it changes when you quit your job.

As far as the progression of who I am today, I can easily say that I wouldn’t be the person I am today without dropping work and starting my self-exploring journey.

If I didn’t leave my job, I might have continued being the same person I was back then. This wasn’t horrible, but I certainly was not the chilled out surfer idiot you guys read about on this blog. (Oooooh, I just came up with a future post idea about who I was 5 years ago, stay tuned!!).

Regarding the Lifestyle …

I was chatting with a friend this past weekend and mentioned that I could have been retired by now if I’d never left my job…

His sarcastic reply was, “You mean you could have been drinking beers under a palm tree all day, surfing and napping whenever you please, never going into an office, just relaxing and enjoying life?”

We both laughed, because THIS IS what my life is already like, now. (I happen to have a palm tree in my front yard that we were sitting under.) Apart from the fact that I have to still make some money somehow, my lifestyle is already quite nice. Working part time is very much like being retired. And many forms of self-employment offer the same lifestyle.

Instead of thinking about the things I don’t have (an extra $1M in the bank), how about I focus on and enjoy the things I already do have?

I’ve touched on this a little before within the stages of financial independence… Once you’ve got a decent sized nest egg and your investments are on auto-pilot, there is a TON of freedom that can be realized — almost as much as if you’ve already achieved FIRE.

When I think about the lifestyle I will have as a financially independent person, it might be very similar to what I already do today.

Shoulda, Woulda, Coulda …

It’s not just 1 decision… looking back, there are a million little things that I could have chosen differently that would have resulted in more money for me today.

But I can’t go back and change the past. What’s done is done, and I am where I am right now.

As much as I love reflecting on the past, I more so enjoy being my rich and happy present self, as well as dreaming of the future.

Wishing you a great week ahead! I sincerely hope you are enjoying and loving what you get up to, no matter how much money you have.

Love, Joel

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  1. VAM October 11, 2021 at 11:11 AM

    ok – I had to laugh on this one – “woulda ,coulda, shoulda” – not exactly money related – but it is amazing how 1 choice drove my life and in the end my financial well-being.

    If I had not graduated HS early and started college the year that I did and at the school that I did:
    1) I would not have gotten a 4-year army scholarship – which lead to my
    a) meeting my husband (now ex sadly) and having 2 wonderful girls and now 5 great grandchildren
    b) having a military retirement pension.
    c) If I had not gone in the military, I would never have earned my MBA in Management Information Systems and thus gone into the world of computers
    d) I would not have traveled the far east and middle east.

    2) If I had not gone earned my MBA,
    a) I most likely would never have gotten to earning 6 figure income
    b) I most likely would never have been on the computer anywhere as much which means I may have missed all the FIRE blogs and education I have received over the years

    3) and all based on a single decision that sent me down this path, I doubt I would have been financially in the place where I get to choose to retire at the end of this year as a millionaire. Which even 10 years ago, I would never have been able to invision ever becoming one.

    I want to thank the FIRE community for all the fantastic advice and encouragement over the years that kept me going and encouraged me to make a lot of changes in my attitudes which led to my financial changes.

    I found DaveRamsey when I was 49 years old. He led me to get myself out of revolving CC debt.
    This led me to actually have some money left over at the end of my pay periods and encouraged me to have an emergency fund.

    Then I found the FIRE community via some of the DR people and my financial life truly changed.

    I do not get to claim FIRE – but I do get to claim FI! I only found the FIRE community in my early 50s. So, while I don’t get to RE, I am retiring the end of this year at just barely 66years of age – and as a milliionaire.

    So, I especially want to encourage those who are not young – that it really doesn’t matter how old or how young you are – today is the first day of the rest of your life and you can make changes and improve your life – if you just take that first step.

    1. Joel October 11, 2021 at 6:04 PM

      CONGRATS on reaching FI! What an awesome story and turnaround. Really proud of you for doing all the hard work and accomplishing things you couldn’t fathom earlier in life.

      And thanks for encouraging others! Share your story far and wide — people out there need it :)

  2. Joe Darago October 11, 2021 at 11:38 AM

    Great stuff Joel! Thanks for the perspective check.

    1. Joel October 11, 2021 at 6:11 PM

      Cheers Joe :)

  3. Accidentally Retired October 11, 2021 at 2:46 PM

    Amazing article! I relate to this so much.

    There are always so many ways we could have made more money. And of course we all see them all in hindsight.

    If I hadn’t left my CEO gig when I did, and hung on, perhaps I’d have saved enough to have mitigated any/all sequence of return risk. Or what about if I had made a few different decisions, I bet we could have sold our company for EVEN more money! I could go on and on.

    But it is impossible to prevent the mind from wandering into this thought process. And like you say, you just gotta say shoulda, coulda, woulda.

    The growth you have had the last few years from not working in that sales job is worth more in the long-run than any money. This is something that I need to remind myself as well.


    1. Joel October 11, 2021 at 5:59 PM

      Hey AR! It really helped me writing all this stuff out. Reminds me that I am blessed with options in life, and taking responsibility for whatever direction I end up choosing, for better or worse.

      Glad you are focussing on the now, and congrats on exiting when you did. I think it was a great move :)

  4. Olaf, the Mile High Finance Guy October 12, 2021 at 11:30 AM

    Joel, it is all a matter of perspective and I struggle with this same topic myself. I left my job when I was burnout earlier this year, despite the fact that 2-4 more years would have made my FIRE number real. However, I realized I have the money to live my life now without regret for 20+ years. So, I quit my job.

    Soon after quitting, I had multiple part-time job offers come in doing exactly what I love: teaching finance.

    Is it hard knowing I could be making large bonuses still? Yes. Do I regret it? No.

    It sounds like you have found peace with your choice, as have I, and that is all we can ask for, isn’t it?

    1. Joel October 12, 2021 at 12:25 PM

      Love this story Olaf. It’s scary taking risks and leaving high paying jobs, but it can lead to really cool opportunities. So glad it worked out for you and you’ve found something better than money (more time and happiness!!). Cheers to that!!

  5. Financial Samurai October 14, 2021 at 3:21 PM

    I hear ya. I could’ve been a 401(k) millionaire by age 40 how do I keep my job. Oh well!

    It’s just money at the end of the day. Fun to do néw things with one’s limited time.


    1. Joel October 14, 2021 at 3:34 PM

      Yep! Glad it all worked out for the best.