How I Actually Quit My Job and Other Hard Money Decisions: Navigating The Leap of Faith

Reading Time: 4 Min

We talk a lot about specific tactics to achieve our retirement dreams here, but the psychology around implementing those ideas is equally important.

Doing something different is uncomfortable.

Sometimes, it surpasses uncomfortable and gets to terrifying.


We confront this feeling all along the way to financial independence. Drive used cars and walk to work, facing the judgment of our peers? Live in the smallest, oldest house on the block?


The problem comes from our frame of reference.


Your Friend Group

The reason driving a used car or living in a crummy apartment feels so scary to you is because it’s very likely your friends are all doing something very different than what you’re contemplating and they all very similar to each other.

In other words, you don’t have someone for reference.


And a single person whom you admire doing the thing you’re contemplating doing is all the difference in the world.

It takes this.


And makes it this.


On Quitting

I have wanted to take a path less traveled many times and not been able to pull the trigger.

For many years,  I had wanted to take a small sabbatical. It began with wanting a gap year before college, then a gap year before possibly going to business school, and then every year thereafter whenever something terrible happened at work.

I kept pushing it off for very reasonable concerns.

And when I finally gave myself a sabbatical, I discovered that all my fears were for naught.

My concern that it would make me lose momentum? As it turns out, it actually gave me the recharge I needed to power through much longer at my job than I thought would be possible.

My concern that it would set me back in my career? My company took me back with welcoming arms and actually appreciated me more because they realized how much I had been doing.

The sabbatical was good practice for me to eventually make the decision to quit. I saw how the world didn’t end, how my prospects in the world didn’t completely implode, and I got exposure to hearing all the fears in my head and doing what I felt was right anyway.

Finally,  I quit my once-in-a-lifetime job at a great investment firm against everyone’s counsel and retired. One of the senior partners sat me down and told me point blank it was a huge mistake, and that the opportunity to create multi-generational wealth was never going to come again for him or for me.

When you put it that way, what I did sounds bold – daring, even.

But here’s what really helped me behind the scenes.

By the time I chose to take a sabbatical, I had had three friends – all of whom I admired and were doing kickass things with their careers – who had already done the same. Their sabbaticals ranged from three months to a year. And they were all so happy with the decision.

And when I quit to retire?

I had one person whom I was very close to who had done it before, as well as a half dozen bloggers who I had been following for years in their early retirements  to make me feel like I was not alone.

So really, I was kind of a big scaredy cat. But even a scaredy cat like me could get comfortable with the path less traveled when there were enough folks holding light up so I could see around the corner.


How This Can Help You

This has big implications for you. If you’re laying awake sweating something at night, try and find someone who has done the thing you’re thinking about and can tell you what it’s like on the other side.

Better, yet find two or three of them.

And don’t stop there. Can’t find that tribe in Hometown USA? Jump online where you can hang with exactly the kind of person you’re looking for.

The unknown looks like a giant scary blob when you have no details. And since as a normal human being you can only see so far in front of you for something you’ve never done before, finding someone who’s done what you’re about to do gives you those little details will give you the comfort and courage you need to move forward.


How This Can Help Your Mom / Dad / Spouse / Girlfriend

One of the biggest challenges I see in the financial independence movement is not the enthusiasm of the person in question for doing the kinds of things FI requires, but what their friends and family think of it. Oftentimes, they have the best interests of the person at heart and being contemplated sound truly terrifying and poorly thought out to them.

If this is your situation, the best thing you can do is to think back to how you might have reacted a few years ago and realize that they do not have the reading, philosophy, and most importantly reference models to point to to give them comfort. You can’t expect them to send you off with their blessing when to them the situation looks like this:


It’s not until they can see that it actually looks like this that you can have a constructive conversation.



Feeling scared is normal, and the way we triumph over that fear is human connection – finding someone who’s done what we’re thinking of doing, and seeing that they’re perfectly fine and even thriving on the other side.

Find those people and pull them into your own life, whether they are real life friends or online buddies.

Time to get in the water. It’s much warmer than you think.



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13 Responses

  1. I was too scared to quit my job. I would have left 3 years of deferred stock and cash compensation on the table PLUS a 7-year partner investment fund that had a 7 year vesting (2017). As a result, I negotiated my layoff in order to keep my deferred comp and investments and get a severance package.

    Did you ever think about negotiating a severance?


    • JP says:

      That is a whole heck of a lot, kudos for negotiating the severance package. I thought about it after reading some of your posts on it a couple years ago but I couldn’t envision a way to make it work at my firm given how young I was and given that they didn’t want me to leave. Maybe I’m missing some of the nuance for how to properly set up for that kind of conversation. I have some deferred compensation that will get paid out over the next few years. Unclear how much it will amount to as it is based on the company’s performance.

  2. Carrie says:

    This is the 4th article I’ve read. I love your point of view on things. Congrats on finding the right path for you.

  3. Nicci says:

    I’m with Carrie, I’m on article 5 and it’s not that I want to be exactly like you or even retire very early. I want financial independence to do so though. My biggest hurdle is where I live in Coeur d’Alene, ID. Companies pay the minimum required and compared to the market value of your job it’s pennies. I realize that living in a big city also comes with big costs but my ultimate goal is to be able to find a job in a big city that I can do remotely in my small town. I’m in Marketing and have almost 5 years of on the job experience and am also getting my MBA as we speak so I feel like it shouldn’t be that hard but it is! I currently make $40,000 and compared to similar positions in other areas of the US it’s well below market value and I feel like I can never save because of that!

    • JP says:

      That makes sense – you want the same freedom but want to then fill it with things that are aligned with your personal interests.

      Are there areas within your specialty that companies in big cities might have a hard time finding locally and would thus be willing to make geographical concessions to hire? A guy I know who moved to Colorado was a software technical lead. I never would have guessed a management+development role could be taken remote, but the market is pretty tight for software talent in all the major hubs right now and this company was competing for great talent against other companies who were paying top dollar, so they didn’t want to chance a 6+ month vacancy and the idea of a technical lead out in CO away from the escalating salary wars in NYC was also appealing.

      There are also some companies like Automattic, the company behind WordPress, who are almost if not completely 100% remote. I checked their site and they currently have openings for a marketing data analyst and a performance marketing person. Sussing out remote-friendly companies may be difficult, but there are a few out there. Wishing you luck.

  4. Sarah says:

    Hmm this is the first article on this site I have read. I saw your story on Cosmo via a Google search related to high paying jobs for women. To be respectfully honest, I’m not convinced. Perhaps I need more back story…how did you get 2.5 million so fast? You sound like a highly intelligent person with skills in investing. You landed a high paying job for a period of time–that helps. And for your expenses to be that low, I humbly assume you are healthy and not needing extra health care and perhaps don’t try to eat higher priced organic foods and such in order to keep your expenses low. Perhaps you don’t own a car either being in NYC.
    So how is someone like me able to do what you do? I guess what I’m trying to express is your scenario is a highly blessed and rare. I would love to retire early, but I’m afraid ‘early’ for me would be age 58. Maybeeee. perhaps the more I read this blog, you’ll open my mind to see things differently. 🙂

    • JP says:

      Welcome to the blog. The answer to all your guesses is yes. I think we all have different circumstances that govern how quickly we get to the same end goal, but I’d suggest that there are core tenets we can all use to accelerate our paths, wherever we each started on the path and however quickly we are initially travelling.

      I know a guy who never made more than $75k a year who retired by the time he turned 40 with $1.5 million. I know a guy who has made $250k-$400k each year the last four years and has literally zero savings. Zero. Sometimes he has to borrow from friends to make rent. Different starting points, different skills, but the opposite of the outcomes you’d expect.

      I don’t what your starting point looks like, but someone like you who is surfing personal finance sites in her spare time has the initiative and discipline that can get to retirement in a few short years. It’s unarguable that short of getting very lucky, an above average outcome requires above average inputs. That means that you will have to cultivate an above average strength compared to reach your goal. Fortunately, there are a number of options for you to choose from (higher income, incredible discipline in spending, creative geographical arbitrage/greatest flexibility, excellence at investing, among others). If one is less likely to happen for you, you can lean on another. We try and cover techniques in each category so you can figure out what suits you best. A few are laid out in Hope we’ll see more of you around.

  5. BL says:

    Hello JP,

    I just started to read your blog following the story in Forbes. I love the short but very directed articles that you have. Great idea to put the estimated reading time on each one as well.

    I retired 3 years ago at 47 (yes a bit older…but I served in the Army so that took a bit of time away!) and I remember going through all of the emotions along the journey that you describe. People woudl say: What? You have not eaten out in 2 years? What? You buy clothes at Goodwill? What? You are leaving a job where you make that much money? I was called odd, strange and someone who was not supporting the economy! But for me each time I save it was a pride point. My wife and I would count things not bought as being that much closer to freedom. I also found that when I finally pulled the trigger I was able to negotiate a severance package that made the jump much easier to take psychologically. Not many companies want you to work for their competitors so with a quick signature to say that I would not they were happy to give my family a nice financial and health insurance package. It is through blogs like yours where we (“the strange ones”) can find a like voice. I will continue to read your blog and suggest it to others.

    • JP says:

      Glad you’re enjoying it and kudos you you and your wife for taking a path less traveled. I’m 100% with you – the freedom is worth more than any fancy meal or designer outfit could bring to the table. What do you do with all your free time now?

      • Ben Poore says:

        Actually…I decided to keep working but in something else entirely. I got certified as a public school teacher and I am loving it! I have been teaching for about a year and a half now. By achieving financial freedom I was able to do just about anything but I felt like I wanted to serve my community again so this was a great option. I know that I can leave at any time but so far I would not trade this for anything else. Plus…still plenty of time over the summer for travel.

        • JP says:

          That’s fantastic, congrats. And I’m sure the passion comes through to the kids since you’re not doing it for a paycheck. Sounds like the definition of a good retirement to me.

  6. Martha Zambrano says:

    I discovered your blog just 2 days ago, this is the 3th article I read from it. I like your point of view.
    You said you had “a half dozen bloggers who I had been following for years in their early retirements…” Who are those bloggers that you follow? I’d like to go check their blogs too, for inspiration.
    Do you know Tim Ferris? He is another source of inspiration for me. He could inspire you for many things too, like for example in how to spend your free time. Tim likes to make “mini retirements” and go to exotic countries for some months to learn new things, for example.
    Do you earn some money from this blog?
    Thank you very much and congratulations! You accomplished the biggest dream of many people from our generation: to escape the rat race at a very young age!
    (English isn’t my first language, so please excuse any mistakes!)

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