Should I stay or should I go? Wrestling with the decision to quit a career

J.D.’s note: In the olden days at Get Rich Slowly, I shared reader stories every Sunday. I haven’t done that since I re-purchased the site because nobody sends them to me anymore. But earlier this year, Mike did. I love it. I hope you will too.

Earlier this year, I sent my wife a text message: “On a scale of 1 to 10, how freaked out would you be if I quit my job this afternoon?”

My wife and I had only been married a short while, but she’d known since our second date that I didn’t plan to work in my traditional job until normal retirement age. She also knew that I hadn’t been very happy at work in recent months.

We’re very compatible financially — both savers raised in working-class families that didn’t always have a lot. We make a point of having what we like to call “Fun Family Finance Day” from time to time. On Fun Family Finance Day, we do everything from competitively checking our credit scores to discussing questions that get at the root of our money mindsets to help us create our goals.

But this question wasn’t part of the plan. Not then.

And it was never on any of the lists of questions that we’d discussed with each other. It was like a pop quiz, a pothole in the smoothest relationship road I’d ever traveled…and I was the one putting it there.

Dreams Remain Dreams Without Doing

My wife and I rarely argue, but when we do it’s usually about food. It’s the kitchen and the grocery store that are our battleground. Our finances are fine. Thankfully, when you’re confident in the life you’ve created and the person you chose to build it with, it’s a lot easier to be honest about what’s on your mind.

That still doesn’t always mean you get the answer you want. Or the answer you were expecting. She responded: “Wait what. Kinda. What would you do?”

A completely reasonable and fair question. Not to mention one that I’d probably have to get comfortable answering from a lot more people.

I think my immediate reaction was: We talk about this stuff all the time, where is my, “No worries baby, YOLO!”? (I must have watched too many romcoms back before we cut cable from our lives.)

Being a grownup, it turns out, is actually really hard sometimes. I was about to learn that talking about something, and actually doing it, are a world apart.

Life is full of dreamers and doers. Sometimes those two personalities cross over. But there are plenty of people who go through life talking about so many things they’ll never have the courage to try — or the discipline and determination to follow through with.

Which person was I? The dreamer? The doer? Or that fortunate combination of both?

Standing on the Ledge

There’s a quote perched atop my bucket list of long-term goals:

“At some point, you will need to take a long look in the mirror and ask yourself not just if this is something you wanted to do at one point, but if this is something you will want to have done.”

Words are meaningless without action. It was time for me to take that long look in the mirror. I thought back to one of the questions that my wife and I had previously discussed: What does money mean to you? To me, once I grew out of the “stuff accumulation” phase of my early- to mid-20s, my answer had always been freedom. Money meant freedom. To my wife, the answer was security. Money meant security.

You can probably see how freedom can conflict with security. That was the case here. Not only that, but I was asking to change the perfect plan, one that she was comfortable with and excited about.

That’s not one, but two shots against financial security. If I’d thought more about our financial blueprints and how they differ, I might have seen this coming from a mile away!

As I was standing on that ledge, about to quit my job, thoughts started to race through my mind. What did I actually have to lose if made the leap? Lots.

• A happy relationship and marriage.
• A secure job with solid income, not to mention a sixteen year investment in my career.
• Great benefits, including lots of time off, health insurance, 401(k) — even a pension.
• The ability to afford anything at any time without any real worry. (Our finances were already on autopilot.)
• My work friends and work prestige.
• The general day-to-day purpose of a job.
• The opportunity to create generational wealth. If we worked until 65, the power of compounding would likely make us ridiculously wealthy.

Today at Get Rich Slowly, let’s perform a little exercise. Come stand in my shoes for a minute, won’t you? Join me on the ledge. Do you see the beautiful view? The endless opportunity? The excitement that’s felt only at the beginning of a grand adventure, an adventure where anything is possible?

Or do you get a queasy feeling in your stomach? Do you feel like you’ve lost your balance, like you’re on the edge of some great catastrophe? Do you see a frightening fall from grace? Does it make you want to back away immediately?

Let’s go back to what it felt like to make this decision…

My Situation

I’m 38 years old. I’ve worked for the same company since I was 22. Corporate insurance is all I know. I’m well paid. I work from home for a solid company with good benefits, plenty of time off, and I really enjoy most of the people I work for and with.

It’s the definition of stability — a solid guardrail protecting me from what lies over the ledge. So what’s the problem?

A year ago, I took a new position that seemed like a great opportunity. Only it wasn’t. The first misstep of my career. A year in, that spot has killed my enthusiasm and engagement. For the first time at work, I’m struggling to get things done.

As an extrovert that derives meaning from helping others, this feels like a prison. My job isn’t hard because it’s stressful. It’s hard because it’s boring me to death! And what are any of us doing thinking about personal finance and early retirement if we aren’t trying to make better use of our limited time on this planet?

There’s a project looming that would require some weekend work once in a while for the foreseeable future, I’ve avoided it in the past, but my luck is running out. My team — and, more importantly, my position — need to take it on. I understand completely. I just don’t want to do it.

At this point in life, my time is way more important to me than money. The weekends and vacations are what I live for. Adventures in the mountains with my friends, quality time with my wife, our dog, and our families – that’s what makes me feel alive.

Insurance? Meh.

No little kid ever said they wanted to work for an insurance company and play with spreadsheets and Powerpoint presentations when they grow up. I wanted to be a baseball player, a sports writer, even a professional forklift driver. (Because what’s more badass than a forklift when you’re a little kid and your dad works at a marina?)

A Glimpse of the Other Side

My wife and I just got back from a delayed honeymoon to Alaska. To say it was incredible would be an understatement. Denali. Kenai. Majestic train rides. Fjords. Glaciers. Bears. Bald eagles. Whales. Hikes.

Life slowed down.

I somehow managed to read five books while doing so many other amazing things. During our more than two weeks off, I got to see what my mind was capable of when it wasn’t drowning in useless information and mundane tasks that consume my braindwidth.

We talked to people who had ended up in this wild place through a history of taking risks. Parents that had hitchhiked cross-country and ended up there back in the 70s. Can you imagine? Where we live, a fair number of people never leave their town or state!

Before the trip, I had tried to apply for a few positions. For whatever reason, it just didn’t work out. I came home from an amazing glimpse into what life could be to a job that seemed like the polar opposite. (Isn’t that every vacation though?) I’ve felt like a square peg trying to fit in a round hole for a while now. Maybe normal life just isn’t for me anymore. Maybe I need something just a little less ordinary.

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Should I Stay or Should I Go?

I’ve been practicing the classic tenets of personal finance since I was in my mid- to late-20s. I found an awesome woman in my mid-30s who just happens to be down with this lifestyle as well. We’re probably two to three years short of where we want to be based on our master plan of a fully-paid house and a really comfortable number in invested assets.

We’d likely fall somewhere between Agency and Security on the stages of financial freedom.

I know good jobs don’t grow on trees, especially where we live. The seasons of the economy are always shifting and there’s a chill in the air. Economic winter can’t be too far off. My wife still has a solid job, and we live a pretty simple life — albeit in an expensive part of the country. Our main splurge is travel, but otherwise we live well below our means.

All of this knowledge and preparation comes with a cost. Having options can be a burden too, because then you’re responsible for making hard decisions. And you’re responsible for the outcomes of those choices.

What other options are there?

• Be a crappy employee/teammate, and still get paid? Plenty of people have played that game. Get a surgery or two, go out on leave, let performance management run its course for however long that takes, and keep cashing checks the whole time. I don’t think I have it in me to put people I respect through that. It’s just not who I am.
• I work from home, and I still can’t bring myself to abandon my laptop. What if someone needs me?
• Am I giving up too soon? The finish line seems just around the corner — somehow so close yet so far away.
• Should I just suck it up and sell a little more of my soul? Slump my shoulders a little bit more as I trade another piece of myself for money I don’t need to buy things I don’t want?

As I go back and forth, sometimes I briefly wish I’d never found the personal-finance community. Like Neo in The Matrix, why’d I have to take the damn red pill? Being a mindless consumer wasn’t so bad. I would have invested 6-10% in my 401(k) with a traditional pension on top of it.

Forty years on autopilot would have produced a comfortable life of work, nice things — and maybe some time in old age to relax and travel.

Facing Freedom

The whole point of everything I’ve done since I started this journey was to be in control of my own life. To not be owned by things or circumstances. To have options. Freedom of choice. F-U money.

I have the corporate battle scars and survivor’s guilt to understand why that’s important.

I’ve sat on the phone while I heard that my old department was closing down. The sadness and tears in the room. Everyone that had taken me in, given me my chance, taught me the job…basically gone, casualties of a business decision.

I’ve seen people get laid off who are petrified because they don’t know how they’ll pay their bills in a couple of weeks. People will be okay eventually though, right?

What about my friend who was struggling last year and left the company? He committed suicide a few months later. Maybe everyone won’t be okay eventually. Depression runs in my family. Am I really built for this? That thought is haunting.

It’s been said that one of the hardest decisions you’ll ever make in life is whether to walk away or try harder. Every bone in my body tells me it’s time to walk away, to bet on myself.

The End?

About six months after the text exchange that blindsided my wife, with her support, I hit send on the scariest, most exciting and important one-line email of my professional career. It would also signify the unofficial end of it: “I will be resigning from my position effective Wednesday, June 26th.”

To combine a few lines from my favorite movie, The Shawshank Redemption, some birds just weren’t meant to be caged. It’s time to get busy living, or get busy dying.

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