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’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.
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.
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!