Exactly six months ago, I walked out of the Apple office for the last time. Just like that, a 13-year career was over.
People leave jobs all the time, it really isn’t a big deal.
But my situation was a little different - at 37, I wasn’t heading to another company. I had no plan to return to corporate life and I was stepping into a future that was completely unmapped.
I was trading shares of Apple stock for a sleeping bag and a backpack.
I remember walking from the office to the parking lot that afternoon, wondering if I had just made the biggest mistake of my life. I had published my first post on Unmapped just a few hours prior, so there was no going back.
This was not an emotional decision. It was a plan built over many years, with checks and balances in every direction. But life is lived in the real world, not on a spreadsheet or in a contingency plan.
In the original post, I stated that “my focus is simple: Build a life I never need a vacation from.”
Would it actually work? Did I really want this? How would I handle not having a paycheck, a title, or a reason to be somewhere at 8am?
If you’re reading this and you’re close to making a similar move or you’ve been telling yourself you’re “three years away” for longer than you’d like to admit - here’s a peek behind the curtain.
There’s good, there’s bad, there’s unexpected.
I’ve also included a playbook on the exact steps I’d take in hindsight if I was on the fence and thinking about making the leap.
Here’s what six months on the other side actually looks like.
Before we get into what’s worked and what hasn’t, let me tell you where my head was at going in.
The most consequential questions came down to two things:
Do I have enough money to do this?
If I’m wrong, can I recover?
The only real unknowns were financial. From a life direction standpoint I had complete conviction - I knew exactly where I wanted to go.
It was just the damn money, I had learned the hard way that there is never enough money regardless of how much you have.
My original plan was to stay until I was 40, which was surely the right move on paper. Staying three more years would have easily added several hundred thousand dollars to my net worth. The obvious move was to keep going.
If you’ve spent any time in the FIRE (Financial Independence Retire Early) world, you know the internet is full of people asking these exact questions. Reddit is loaded with posts of young people seeking permission to walk away, the issue is nobody ever provides a follow up.
What actually happened? Do they regret it? Did they have enough?
We see their worries, hopes, and dreams on the front end. But we never find out if it actually worked.
I’m only six months in, but I can provide preliminary answers. That’s exactly what I’ll do today.
A Quick Disclaimer: This article is for people who have accumulated significant assets and are considering retirement or looking to make a radical career change.
I realize that excludes a large percentage of readers. If you’re earlier in your financial journey, take a look at the paths I referenced in this post - and feel free to fill out this form if you want to talk through it with me.
One last thing - I was dealt a fortunate hand. Working for a great company, in a well-compensated role with access to stock, and enough discipline to save aggressively for over a decade. But plenty of people were dealt the same hand and never played it. At some point, opportunity has to meet execution.
What Has Been Amazing?
Unquestionably, the biggest positive impact this decision has had on my life is lifestyle flexibility - being the author of my own daily life.
In my old life, I would wake up at 4:45am to give myself enough time to workout before heading to the office. I’d commute nearly two hours a day, get hundreds of texts and dozens of phone calls, and sit in meetings that were largely preparing for other meetings.
I’d count down the days to the weekend so I could finally do something I actually wanted to do. I’d feel guilty going on vacation. I’d check the stock market and the price of AAPL 50 times a day because it was my ticket out of the rat race.
Six months later, I’ve spent 76 nights of 2026 either traveling or camping in the backcountry.
I don’t wake up to an alarm. I spend the first 90 minutes of my day focused on health - walking in nature with my girlfriend and dog, a sauna, a cold plunge. I’ll work on something creative for a few hours. I’ll hit the gym or go on a mid-afternoon run. I’ll sit out on the porch and read a book or listen to music.
My phone used to constantly light up with work notifications, almost to the point of giving me PTSD (not even kidding). These days I barely take it with me and make a handful of calls per week.
A second underlying theme is that I am a significantly healthier person, both physically and mentally.
Rather than squeezing a workout in at 4:45am, my entire day is intertwined with movement, health, and wellness. My stress levels have dropped dramatically. My screen time is down over 50% - I'm now under 2.5 hours per day (still have work to do there).
Lastly - relationships are better because I have the time and space to devote myself to them more than I was previously capable of.
In the past, nearly every family gathering eventually meant stepping outside to take a work call. Nights, holidays, weekends. By year twelve, nobody even questioned it anymore, they'd just say "oh, Kevin's working again."
The 6 Month Verdict: I am a healthier, happier person who gets to spend each day doing exactly what he wants to be doing.
What Has Sucked?
Not everything is perfect. In fact there have been a lot of challenges - nearly all of them mental.
When you leave your career, your shortcomings will be amplified and met with plenty of white space to worry, catastrophize, and assume the worst case will happen.
For me, a lot of this ties back to my relationship with money.
I had a plan - I had 1.5 years of cash in an account earning 5% to live off of. I wouldn’t touch the money in the stock market, so there was no point in even looking at the market.
But we live in crazy times. Geopolitical instability, multiple wars, a never ending chaotic news cycle that sends the market skyrocketing or spiraling.
I found myself back to checking the market constantly, mentally calculating how safe I was.
This became such a problem that I had to set a rule - no checking the stock market or my net worth for six months. I’d schedule a dedicated financial review on June 1st to determine my position.
I failed many times. I’d find myself breaking down and looking multiple times per week and it would impact my emotional state for the entire day.
When I sat down on June 1st to calculate my net worth, I found it not only at an all time high, but up many multiples of my annual cash burn this year alone. All of that mental energy, all of that daily worry and my net worth had never been higher.
So the question is - why even look? This is still an open mental battle I face daily (Note: At the time of writing this, I failed again today and I’ve lost more money today than I made my first year out of college. Still battling the devil on my shoulder).
For me, it wasn’t just money - I saw other personality traits amplified and have a negative impact on my life.
When you remove the job, the personality doesn't change, it just finds a new target.
Up until 2026, I’d spent my entire life hard charging. I’d outworked everyone up until this point and convinced myself that white-knuckling life was the ticket to success.
When it came to training for my thru-hike of the Benton MacKaye Trail, I built a brutal training plan and treated myself like I was a professional athlete. I had the time, why not?
After nearly 2 months of training 15+ hours per week, I crashed and burned. My body was constantly sore, mentally I was exhausted, and all of my biomarkers were thrown off.
My doctor told me clearly - I was overtrained and needed to take my foot off the gas immediately or my BMT thru-hike was at risk.
I caught it just in time. The thru-hike was successful - but my hard-charging personality, left unchecked with all that white space, nearly derailed the biggest goal of my year.
The 6 Month Verdict: Your shortcomings will be amplified when the career is removed. Mine were my relationship with money and a lifelong habit of white-knuckling everything.
What About the Unexpected?
While there have been some key themes in the first 6 months, there are even more unexpected learnings.
Here they are:
Nobody Cares About Your Career: Lots of high performers are trapped in status games and worry about losing their identity if they leave a prestigious job. Here’s the secret - nobody gives a shit about your career. I rarely ever get asked what I do for a living. And if a person does and I tell them, 100% of the time the response is “Wow, good for you.”
Boredom Myth: Almost everyone I talked to before leaving Apple warned me that I’d get bored. Everyone else my age is working, it would get lonely. This couldn’t be further from the truth for me. The reality is, I am just as busy now as I have ever been - I’m just doing things I actually want to do with my life.
People Are Interested: I had no intention of sharing this journey or my learnings on the internet, but I made a decision on a whim in the last week to start Unmapped. Since then, I’ve had many amazing conversations with people and I’m still shocked to realize that nearly 1,400 people care enough about a guy living a contrarian lifestyle to subscribe.
I was Ready for the BMT Thru-Hike: I spent hundreds of hours training, preparing, and worrying about my first thru-hike. When it actually came down to executing, I was incredibly ready. This was a major lesson for me - sometimes it’s okay to let go and trust yourself.
The 6 Month Verdict: Most traditional advice comes from people who haven't actually done the thing. People respect and draw inspiration from those who take unconventional action.
Your Playbook
If you are in a similar position and have a goal of leaving the corporate world or making a dramatic career change, here are the exact steps I would take based on my learnings.
Living an unconventional life requires unconventional thinking.
Here’s the playbook:
Step 1: Talk to Somebody Who Has Actually Done It
For every huge goal I set, I talk to somebody who has done it before me. This allows me to fast track the learning curve and avoid obvious pitfalls. I’ve done this for backpacking, trail running, and whitewater kayaking.
I also did it for early retirement - I worked with Jillian Johnsrud during this life transition and it was incredibly valuable. She had already done the exact thing I was about to do, so I was able to learn from her mistakes. We met several times before I left Apple and then again after a month on the other side. I highly recommend her as a resource.
I’m also open to chatting with anyone who is on the fence or thinking about taking the leap - I can go deeper on some of what I shared in this article.
If you’re interested, fill out this form and I’ll reach out to you.
Step 2: Create Your Money Rules Before Leaving
Prior to leaving your career, you need a clearly defined financial plan and set of rules that you live by. If you avoid this step, you will get eaten alive mentally.
Here’s what you should consider:
Note: I'm not a financial advisor - this is what worked for me. Please consult a professional before making major financial decisions.
Money Plan: Clearly define the amount of money you intend to spend per year and where the money is coming from (Savings Account, Market Withdrawals, Side Hustle, etc)
Cash Buffer: Setting aside a cash “buffer” to live off of has been incredible for my psychology. Not needing to pull directly from the market in a volatile time has been worth its weight in gold. I’d consider 6 months to 2 years cash, depending on your risk tolerance. I keep the money in a Mercedes Benz Demand Note account earning 4.5%, but you could also use a high yield savings account.
Freedom Math: Every $1,000 you make per month reduces your FIRE number by $300k. Read my Freedom Math article, this can be a cheat code in reducing financial stress in retirement. Finding a simple side hustle with your newfound time can have massive ROI.
Set Rules on Checking Markets & Net Worth: Since you have a cash buffer to live off of, do everything you can to avoid looking at the market or your brokerage accounts. Delete the apps off of your phone and set specific days/times to review your financial situation. I review basic tactical financial details (Paying bills, checking account balance, etc) every other week and I have dedicated scheduled sessions for strategic reviews. In 2026, I have 2x dedicated meetings with scheduled iCals to review my Net Worth & stock sale strategy.
Step 3: Have a Plan For Your Daily Life
The worst thing you can do is leave your job and then figure out what you will do with your life afterwards. Doing so will put you on the fast track for boredom and likely feelings of depression.
There are 2 things I would do ahead of time, giving yourself many months to think through:
Define Your Dream Day: I spent at least 12 months ahead of leaving thinking through exactly what my “dream day” looked like. Quite literally, I mapped out what a perfect day would look like in my life from the second I opened my eyes until I went to bed at night. And then I started living it when the job was removed, but I knew well ahead of time what would fill my hours. What time would I wake up? What would my mornings look like? Who would I spend time with? What hobbies could I explore further?
Setting a Huge Goal / Mission: Many people tie their self worth to their careers and feel lost when it is taken away. Knowing this ahead of time, I set a very ambitious mission for 2026 (Backpack 1,000 miles & write about it online). This has not only motivated me during tough times, but it also gives me daily purpose and something to look forward to. I would highly recommend setting a massive goal that defines your entire retirement year and having this well established before you leave.
Step 4: Identify Your Personality Traps
Your shortcomings will be amplified when your calendar is completely blank and career responsibilities are taken away. Whatever personality traits have caused you to spiral in the past will show up loud and clear.
This was something I did NOT prepare for or know about, so learn from my mistakes.
Take some time and think through:
What am I most self conscious about? How does this manifest itself in my life?
What bad habits show up in my life when I am bored, lonely, or depressed?
Are there any personal relationships that struggle when I am bored, lonely, or depressed?
For each of these - proactively map out a plan on how you will respond when they arise. Because they will.
For me, I have a scarcity mindset with money - The solve for me is to set rules that help me avoid spiraling (Cash buffer, not checking markets, etc).
Step 5: Contingency Plan
Before leaving your career, have a solid backup plan that you can deploy as needed if things go sideways. Nothing ever goes to plan - Markets crash, family situations change, unexpected costs happen.
If you are in a position to leave your corporate career, you have incredible skills that are an asset. Take some time and map out 1-3 ways you can begin generating cashflow in a 30 day window as needed. This can be in the form of a job, consulting, or starting a service based business.
For me, my logic has been:
Keep my network warm, playing the long game
Understanding my skills don’t expire and are worth a lot of money on the free market
The corporate world will still exist if I need to return
I’m okay working a lower level job than I had in the past if I have to. I am not “better than that” in my mind.
The worst case scenario is I tried something bold and went back, which is not actually a catastrophe
Taking the leap of faith from a corporate career to something undefined is challenging, but you have the ability to stack the deck in your favor.
These five steps are all about being proactive and making you resilient, allowing you to thrive no matter what happens in your life and in the world.
You can't predict every problem or fix everything ahead of time. But this allows you to live life on your terms - which means you're actually living your life.
Kevin
What a gold mine of authentic insight. Such a gift to hear from someone relatively fresh and in the thick of their journey of a huge life pivot. Such a great read - many thanks for sharing, good sir.
First, thanks for sharing your story.
I’m retired now. Reading (or hearing) about other people’s adventures throughout my life has been initially inspiring followed by truly inspiring once you find out they lived to tell the tale! 😁
Safe & joyful travels to you & keep on sharing!