I’ve worked incredibly hard to get to where I’m at in life.
There’s no doubt about it.
After being fired from my service advisor job during the depths of the financial crisis in the spring of 2009, I found myself an unemployed college dropout who was deeply in debt.
Not a fun position to be in, especially when you’re already entering your late 20s.
It was one of several “dark days” I’ve experienced in my life.
Down but not out, a plan was devised.
Developing And Executing A Plan
That plan, which was developed by yours truly, involved a number of moving parts (parts that shifted and/or became clearer over time) that I’ve shared over the years.
It involved moving across the country to take advantage of domestic geographic arbitrage, getting a higher-paying job, selling my car, cutting expenses to the bone, tracking every penny of income and expenses, making intelligent investment choices, etc.
Major elements of this plan that I think can be replicated in order to retire in just five years have been discussed with depth in my newest best-selling book: 5 Steps To Retire In 5 Years.
Now, developing a plan is one thing.
Executing it is quite another thing.
But executing it is exactly what I did. With brutal efficiency, no less.
Look, nobody did anything for me.
Nobody showed up to work for 50+ hours per week for me.
Nobody got up early and rode the bus to and from work for me.
Nobody ate my ramen noodles and PB&J sandwiches for me.
Nobody wrote articles for me.
Nobody researched and made investments for me.
It was all Jason.
The plan obviously worked out tremendously well. Better than I had originally thought it would.
Originally conceived as a plan that would perhaps allow me to quit my job by 40 years old, I ended up quitting my job at 32. And I found myself financially free at the tender age of 33 years old.
I now live in Chiang Mai, Thailand as a dividend expat.
I’m living an incredible lifestyle, all funded by the passive income I spent a few years of my life wholly dedicated to building via my FIRE Fund.
But I’ll share a little secret today.
I sometimes experience impostor syndrome.
Impostor Syndrome
I occasionally feel like it’s not me living this life, as if I don’t deserve it.
There’s this feeling deep in my mind that creeps up to the surface once in a while, making me ponder if my accomplishments are really my own.
And I sometimes wonder if this all really happened. It feels like a dream that I can’t possibly be living.
Speaking of dreams, there’s a recurring dream that I have almost every single night of my life.
I don’t believe I’ve yet publicly shared this, but I guess it’s finally time to let the cat out of the bag.
The dream (or is it a nightmare?) is that I’m back at my old job. I’m a service advisor. I have my old desk, with the monitor, phone, and paperwork arranged just as I remembered. I’m doing paperwork, answering the phone, checking emails, and dealing with the constant flow of clients and technicians.
There’s a problem. Parts for a job haven’t arrived…
Then there’s another problem. A repair is turning out to be far more expensive than originally conceived…
One problem turns into another problem until I wake up from my dream, slightly sweaty and worse for wear.
The weird thing is, every dream is different. It’s like I’m actually “showing up to work” almost every night. It’s miserable for me. And I don’t know how to fix it. If it were the same dream every night, my brain might be able to recognize it and turn it off. Instead, I get a new show every night, much to my bemusement and dismay.
Moreover, the details make it feel real. Very real.
I can see people, hear their voices, smell the air, touch my keyboard, etc.
It’s almost as if I’m being transported there, into some alternate universe.
But that alternate universe exists only within my own mind.
And I think it’s my mind holding on to the past, refusing to believe that I was actually able to do all that I did.
As much as I want to believe – no, as much as I do believe I did everything I’ve done and I’m actually living out this life – there’s a small piece of me, somewhere deep down, that thinks it’s all just a dream.
It’s almost like there’s been a glitch in the Matrix.
It’s like that moment in Vanilla Sky when the narrative shifts from the real to the imagined.
Yet I wake up each day, still living this life.
I’m still here. I’m still young, financially independent, and blissfully happy.
Pragmatism And Optimism
I’ve long been an incredibly optimistic person.
I have a good attitude that fills me with joy and gratitude for everything that I have.
But I’m also very pragmatic.
And growing up in a crack house in Detroit, watching your dad leave you at eight years old, experiencing your mom giving you up at 11, struggling to get footing in life, dropping out of college in your junior year, getting the phone call about your mother committing suicide at 20, and wasting a relatively sizable inheritance inside of two years in your early 20s doesn’t exactly add up to believing that you’re going to go on to achieve wonderful successes early on in life.
I think this issue will self-correct itself over time. I just have to get used to this lifestyle of complete autonomy.
Things are still fresh for me. This dream feels like, well, a dream because it’s occupied such a relatively short period of time in my life.
I’ve been alive for just over 36 years. And I’ve had a job since I was eight years old in Detroit, cutting grass and shoveling snow so that I could have money to buy food and do kid stuff (like play arcade games down at the local corner store).
I’ve been working for most of my life. And I was doing so because I had to. I didn’t have a choice in the matter.
If I didn’t work and earn money, I didn’t eat or have shelter.
It’s a pretty easy call. Show up, do your tasks, and make your money.
But I only became financially independent three years ago.
And even for the first, say, two years, it was still a little tough, because I had to scrimp and watch every penny in order to make sure spending was under passive income.
I might have been free from my job. But I wasn’t free from worrying about money, which is a way more fantastic level of freedom.
So it’s actually only been about a year in which I’ve been totally unleashed, able to do whatever I want. That’s a very small percentage of the years I’ve been walking around.
There are no rules to my life. I can pretty much do, or not do, whatever I like.
That’s, honestly, a very strange feeling for someone who grew up so poor and faced so many challenges.
I’m glad I grew up poor. I truly am. It gives me an appreciative perspective that I think is a real asset.
However, I guess I always felt like the big challenges would never end.
I got so used to them, and I had to develop such a resilient shell to my psyche, that I suppose I always assumed that life would be one constant struggle. I evolved and adapted for what life was throwing at me… until, well, life suddenly became easy.
An Easy And Wonderful Life
And now I’m no longer a soldier in that battlefield. I’ve been plucked out of the trenches and placed into a life of comparative comfort.
And that has been, at times, discomforting.
Not only are there the doubts about whether or not I actually could have done all of this, but there’s also the empathetic guilt that creeps over me, giving rise to existential questions about my role in this world and the good fortune I’ve been gifted (versus the misfortune billions of other people have been “gifted”).
So there’s the: “Me? How?”
And there’s also the: “Me? Why?”
But I’m getting better.
And I continue to seek out new challenges. I continue to do my best to grow as a person and become a better version of myself every day, which keeps my edge sharp. It keeps me comfortable to have a little discomfort.
While I still “see my old workplace” almost every night during my sleep, I’m feeling a little bit less like an impostor with every day that opens up and allows me the opportunity to see my financial independence and lifestyle for what it is: a well-deserved position that I worked incredibly hard to attain
Furthermore, I work incredibly hard to maintain my “street cred”, if you will – I do my best to make the most of this unique and amazing opportunity. It’s not just something I deserved. It’s something that I want to continue to deserve. I want to continue to fill my internal scorecard to the brim and earn that worthiness.
And the upbringing I’ve had allows me the perspective to appreciate my newfound freedom, all while also recognizing how good I have it (and mostly had it all along). That will surely fuel greater philanthropic ventures as I progress throughout my life.
Conclusion
So what can we do if we feel like an impostor?
I think we have to have an honest and introspective conversation with ourselves and with others (especially those that were able to tag along while you rose to greater heights).
Reflect on the challenges you overcame, the hard work you put in, and the growth and evolution you’ve experienced as a person.
The past you would surely be proud of this current version of yourself. This is why you fought and kept moving forward.
It’s okay to give ourselves credit where credit is due and enjoy the rewards of that which we worked hard for.
And I think we have to make the most of this lifestyle. Don’t squander it. Time is a great friend, for it will give us additional compounding and moments to do more with this amazing and unique opportunity, all while simultaneously allowing us to adapt to and accept our freedom for the well-deserved gift it is.
The best way to not feel like an impostor, in my opinion is to simply not be a fraud. Be genuine and authentic. Own the freedom and use it as a platform to better yourself and those around you.
What do you think? Have you ever dealt with impostor syndrome after FIRE? If you’re not FIRE, do you think this might be something you’ll experience?
Thanks for reading.
Image courtesy of: Sira Anamwong at FreeDigitalPhotos.net.
P.S. If you’re interested in becoming financially independent and retiring early in life, check out some great resources that I personally used to become free at 33!
Hi Jason,
Great article and thanks for sharing this. I often have anxiety type dreams, especially as I keep pushing myself to produce new content or output.
That may be one manifestation of your dreams. Sometimes our dreams help purge the feelings and memories that lie just below the conscious levels of thought.
Alter your outlook to embrace the challenge in the dream and see if the memory of the dream becomes less traumatic when you wake up. Then the emotions will hold less power over you and be released.
Stay well,
Mike
Mike,
Yeah, it’s weird. I don’t ever feel anxiety or anything like that in my day-to-day life. I mean, things are pretty perfect, so I’m not looking for any sympathy. But I guess there’s a piece of me that almost can’t believe that I went from so low to come out so high – in a relatively short period of time, no less. It defies belief, even though I (obviously) saw myself execute everything along the way. I don’t think many people see life from such different altitudes like I have.
Anyway, just sharing thoughts and experiences in the post-FIRE life, with all of its ups and downs. I think these dreams (or nightmares) will eventually subside. This is all still pretty new to me. I haven’t been living this free for very long. One more reason to believe that things are getting better every day. 🙂
Best regards!
Hey Jason, thanks for the article. I also took the time read the article you wrote not too long ago regarding your thoughts on suicide. I enjoyed reading both and I respect your ability and willingness to be transparent with your life’s experiences – certainly not something that comes easy for many people, especially in such a public forum as a blog.
I read an article this past year (can’t remember who published it) but the focus was the same topic – imposter syndrome. Per the article, this is a fairly common “syndrome” among young lawyers who secure entry level staff positions in large firms making well into six figures, despite the the long hours common within the industry. The transition from being in school for 23+ years of your life with very little work experience (whether it was flipping burgers or otherwise), if any, and incurring debt for much of the last 7 years of that schooling, I can imagine it feels a bit unreal when a young graduate sees his/her first paycheck from a large law firm. I find this topic interesting and I wonder how many successful entrepreneurs feel this way after they start and grow a company and experience a significant windfall when they sell the business or perhaps go public.
Thanks for sharing!
PIV
PIV,
Thanks for the kind words. Really appreciate that. It’s a lot easier for me to write investing/stock/money articles than the pieces that focus on more personal and profound matters, but I enjoy that challenge. I like putting myself out there and helping/inspiring others in the process. It forces personal growth in many ways. So it’s a win-win. 🙂
I did a bit of research into this phenomenon when I was trying to explore for myself what was going on. It’s an interesting thing. It seems to come down to a combination of disbelief, shock, guilt, and sudden change in one’s life.
For me, it really just manifests into the dreams I have. In my daily life, I never feel anything related to any of this. But there is obviously something deep inside of me that kind of refuses to believe that I’m not still that poor kid struggling in the ghetto. You struggle for so long, you begin to think that’s all there is. I was determined to dig out of that. And I got out with my own two hands. But you sometimes still feel the weight of that shovel. It’s something that stays with you a little bit.
Thanks for dropping by!
Cheers.
I was one of those lawyers back in the aughts The issue is very real, you don’t yet know what you are doing, you never see feedback given to other attorneys, only your own work, and given that you’re probably a natural pessimist to begin with (law school does that to you) it can really get you down. The way I dealt with it was common – spend too much money on restaurants, bars, and trips out of town.
The silver lining – the compensation was good enough that I managed to save some money anyway, so when I discovered the concept of FI through blogs like MMM and Dividend Mantra, I had a head start on early retirement. All I had to do was shift my savings over to investing and keep adding more every month (and stop eating out so much). After that, it only took 2-3 more years for my investments to hit 25x living expenses. Young lawyers take note!
HW,
Awesome stuff. Thanks for sharing that!
Cheers.
Hi Jason. I am a simple person so I will give a simple response to your problem. Financial success is when you are rewarded for your hard work , dedication and making good choices . However , financial success by itself is a hollow shell . You have to feed your spirit to obtain emotional success. People obtain emotional success in different ways . You have to find the right way for you. Some things that I believe help achieve emotional sussess are having a wonderful woman to share your life , having a dog to give unconditional love , strive to call upon the positive and good things in your life not the negative things from the past. The more you call upon the good things in your life the less power the demons from your past will have. Learn to enjoy and appreciate the little things that life has to offer . Enjoy your financial success you deserve it !!!
Jax,
Thanks for the suggestions.
I’ve actually written articles about most of what you’re mentioning here. And I have most of that in my life. My daily life is actually wonderful, which is why, I believe, I’m running into this in the first place. Perhaps I didn’t articulate that well enough in the article. This is more of a personal rumination. It’s a sharing session of an interesting thing happening deep down inside of me somewhere, manifesting into these recurring dreams.
My conclusion is, it’s just a thing where I’m not quite used to FIRE quite yet. It’s still relatively new for me. My life has been 99% struggle, 1% dream life. That dream life (the one I’m living now) started up not too long ago. As that percentage split becomes more advantageous, I think this, too, will pass. Then the life in my dreams will be as good as my dream life. 🙂
Best regards!
Jason, You are amazing for several reasons. The odds of anyone accumulating almost half-million net worth coming from your troubled childhood, from a broken family in one of the most challenging cities in the world to raise a family are next to none. You have overcome those seemingly insurmountable odds, so full credit to you! The other day, when someone was complimenting me on my blog and about my $3 mill+ net worth, I said it aint so great given the loving family, amazing debt-free graduate education and career opportunities I got in my career. What would be miserable is if I had squandered the head-start, which I thankfully didn’t. I told them that to get truly inspired, they must visit your blog and understand your life journey.
TFR,
Thank you very much for that. Really appreciate it. Very kind of you. 🙂
I guess it’s all relative. For people who are used to success and money, it’s perhaps not particularly special or different if you end up in a pretty good spot early on (or even later on) in life. The change in my life altitude over a short period of time, however, is maybe a little jarring. And I’m adjusting to being way up here, when I got so used to being way down there. It’s a strange (but amazing) feeling. And there’s something deep down inside of me that almost can’t believe it all. It refuses to let go of that struggle. I think the dreams (or nightmares) will disappear over time, as FIRE becomes a much larger percentage of the time I’ve been alive.
Congrats on all of your own success over there. It might not seem special, but there are so many people who waste those same opportunities you’ve been given. I was just reading some story about a judge in the US that released financial statements – and just, wow. Guy took on loans against his retirement accounts. Sheesh. How so many people can be so bad at managing money never ceases to amaze me.
Best wishes!
Thanks Jason. Can’t believe about that judge – supposedly the most “learned” of all professions! The world needs many inspiration models for FIRE, indeed. Not that the mainstream cares.
I quit my job back in April and was fine all summer, but in the last few weeks I’ve had work-related dreams. My best guess is it’s because I worked at a university and school is back in session now. This was normally a hectic time of year, so my mind is still ready for that back-to-school chaos.
In one dream that felt the most real, I agreed to work part-time and was talking to my supervisor about some projects that needed to be done. He said he would need me to come back in that evening around 7pm when everyone else was gone so I could do some upgrades. (I was in IT, yet I was never one to go back in during off-hours.) I woke up from that dream in a panic thinking I made a huge mistake going back to work part-time. A wave of relief and joy washed over me as I realized it was just a dream and not only did I not have to go back that evening, but I never have to go into that office ever again!
Travis,
Hey, I love this comment. Thanks for sharing. That last part really spoke to me. I usually wake up from my dreams in a bit of a sweat, because they feel and seem so real. Then a sense of relief washes over me as I realize it was just a dream.
So I’ve been looking at it from the sense that’s a bit of a strange curse that’s following me around. But now I see it as a regular reminder of just what I left behind and never have to come back to. 🙂
Thanks for that!
Cheers.
Hi Jason very interesting thoughts and conversation. I have a recurring dream were I’m poor and homeless with a shopping cart and people are beating me up stealing my stuff ! So real it even wakes me up ! My wife chuckles and says Ohhhh that will never happen… Hmmmm well I dont know about that my road to were I am have been well VERY bumpy to say the least.
I think our subconscious is there to keep us in check so to speak. I never want to forget were I came from so that I can keep and eye on not getting in a bad position when I’m older and unable to recover as I did in the past when I was younger.
Kind of an off topic note.. Every state in the USA has Eschew laws and will take your property ( including stocks ) if it appears to have been abandoned. This past month I had my 50 shares of Regions bank Eschewed by the state of Mass ( I have not lived there since 2004 ) even though I have the certificate I still lost them, and the state of Florida ( were I now live ) Eschewed a small checking account I had as safety money ( Ha Ha so much for that ) because it was unused for over a year !
Make sure you are active with ALL your accounts, do make sure you vote your shares every year and respond to any other correspondence or it WILL be taken.
Keep up the great work 🙂
Bob,
Yes, these dreams keep us humble. That’s for sure! 🙂
Sorry to hear about the account issues. I think you’re talking about Escheatment. I’m aware of it, but it’s usually triggered after a very long period of inactivity (5 years or so). You should still be able to get your hands on the money, but I imagine you’d have to go through the unclaimed property rigmarole.
Cheers!
I used to have work related dream all the time. My mind was trying to cope with a stressful environment. After I left, I never had another dream about work. It’s so freeing. I can let the past go so I didn’t have a big problem with the transition to retirement. I never felt I was an impostor, either. 😉
Enjoy your dream life! You deserve it. BTW, I might see you sooner than I thought. I plan to spend 3 months in Thailand next year. Something came up and I need check out some stuff.
Joe,
That’s awesome. I’d rather be in your shoes, without the recurring dreams. I think they’ll go away at some point. It’s just that I’m still getting used to all of this. I’ve been poor and struggling for most of my life, so it’s all still a little bit surreal.
It’ll be great to have you in CM. Definitely shoot a message when you’re in town. We’ll have to get some lunch! 🙂
Best regards.
Honest post Jason. Personally no issues with dreams, but I rarely had those when working either. But the feeling that you are in imposter and that it’s too good to be true, sound very familiar!
Not sure how to deal with it, it might just fade over the years as you accept the situation more. You certainly earned it, so don’t fret about that!
CF,
Yeah, it’s super interesting. I guess it keeps me humble and appreciative. It’s tough to forget how it once was when I’m reminded almost every night. I try to see the bright side. 🙂
My change in life trajectory has been probably more extreme than 99% of people. To go from the ghetto of Detroit to relatively wealthy in Thailand – that’s a change in mindset, situation, wealth, culture, and geography that’s pretty tough to match.
I agree with your conclusion. I think it’ll naturally change as I experience more of this post-FIRE life. It’s still really new to me. My life has mostly been a struggle. Had a tough go of it with money, family, work, etc. To be so blissfully happy and free of concerns is still a little jarring. But I wouldn’t trade it for anything. And I’m totally aware that I worked hard for it and earned it.
Thanks for dropping by!
Best regards.
You got a good point there, with so many struggles in your life previously, it must feel strange to have so much piece of mind. I guess that does take time to settle into your mind properly. I personally cannot relate, as I have had a very good life so far with very little issues. I’m very happy with that obviously, but it also make it more difficult to relate to those that where not so lucky. Anyhow, Jason, you are doing great my man. Please keep going!