Special Report: Build Your Retirement Escape Hatch
You need to build your Retirement Escape Hatch before you’re ready to retire. This is not a side hustle. This is an intentional effort to engineer meaningful income for the rest of your life.
You’re finally taking that trip to Hawai’i you’ve been promising yourself for years. And why not start your adventure on Oahu so you can see some of the sites where Jurassic Park and Jumanji were filmed? How can those movies not hold a special place in your heart?
You can’t wait to relax on the famous North Shore beaches of course, but you’re really looking forward to the horseback tour at Kualoa Ranch, through the valley where they filmed the big dinosaur stampede scene.
You find out while you’re there that they have the Jurassic Valley zipline tour; a 3-hour adrenaline-filled adventure! You haven’t really budgeted for this, but, what the hell, you’re here and it sounds amazing. Let’s do this!
But tragedy strikes. There’s a hitch in the line and your harness comes unhooked and you plummet 20 feet into the foliage below. Your left elbow shatters on impact. Disaster! But fortunately, the Kahuku Medical Center is only 10 minutes away.
“Oh man, the rest of the trip is a bust,” you think as you lie there waiting for transport to Honolulu to put pins in your shattered arm. How are you going to pay for this? And how long will it take to recover physically and financially from this?
One medical emergency…
Budget blown. Trip ruined. Bummer, dude.
Now imagine this is your financial situation for the rest of your life after retirement.
The Traditional Retirement Model Is Failing You
If you’re like me and waited until your late 40s to start saving for retirement, you know you have a problem.
Perhaps it’s dawning on you that you don’t even have a real handle on a dollar amount that would fund your retirement until you die. But you know you won’t have enough by 65.
This is the gray area where the traditional retirement model will fail us when we need it most: the end of life. This is when we are at our weakest and most vulnerable. This is when we need the most security. This is the hardest part to plan for.
It gets worse for about half of Gen Xers who have been busy through their 30s and 40s just paying for everyday life, let alone amassing any meaningful savings. We have seen costs go up, benefits go down, pensions disappear, the markets playing yo-yo with our investments.
In fact, while a mere 16% feel they have saved enough for retirement, 53% of Gen Xers have not done ANY retirement planning. Have you thought about how long you will have to work to be financially secure until you die? Because it’s probably longer than you think.
But here’s the thing. Like many Gen Xers, I’m not so concerned with when I will retire. We’ve seen what happens after retirement. Many people lose connection, camaraderie, purpose. Depression sets in. Many of us are watching it happen in real time to our parents’ generation. Stop moving, start dying.
No, what we’re more worried about is that we stop working and find out too late we don’t have enough.
We outlive our money.
But I sure as hell don’t want to be doing what I’m doing now for 25 more years. And I’m willing to bet, neither do you.
How Do We Even Get To Retirement?
You may already have a planned side hustle you intend to pursue in retirement. You may have already tried and failed at one of the innumerable opportunities presented out on social media and every other feed imaginable.
Many of these sensational methods to “make money doing little-to-nothing” have outsized successful outcomes ($100K+/year) around 1-2% of the time, while 80-85% make less than $1000 per year. The ads highlight the top 1-2% of course. Pretty brutal.
A side hustle is not the best choice for a source of predictable long-term income in your post-retirement years. Usually it’s just more unsatisfying work that dictates your time. But we’ll come back to that.
First let’s look at what we have available to get us to retirement in the first place. And where the inherent fault lies with counting solely on retirement planning to fund your life until death.
The problem isn’t that financial planning doesn’t work; it does. The problem is that in many instances financial planning is performed with the best-case scenario in mind, with very limited visibility into future risk management contingencies. You can plan for some hypotheticals, but at best, it’s a best guess.
There is no crystal ball. Nor do we have Biff Tannen’s copy of Grays Sports Almanac to bequeath to our younger self. And humans tend to have a rosier outlook on life outcomes than reality tends to dish up anyway. We’re damn fine optimists.
The principles of diversification, portfolio balancing, cash liquidity, debt elimination, and so on are proven, rock-solid guiding principles that can generate not only semi-predictable growth, but also peace of mind.
But these are the things we can control. So much else is just out of our hands.
For one thing we have no idea how long we are going to live. Extended human longevity is not an aberration anymore; it is trending towards the norm. 40 years old is no longer “over the hill.” Midlife can now reasonably be considered age 50-70ish. That’s a whole new life phase not available to, or planned for by, previous generations.
Then consider the arc of technology. AI is only the latest in a string of technological advances that put individuals’ livelihoods at the discretion of the world’s richest. (I’m thinking about near-earth orbit billionaire-class doomsday bunkers to escape a poisoned planet!)
This leads to unpredictable market conditions. And let’s not forget shareholder value as the driving economic factor; corporate greed; increasing hostility and war; climate change; the degradation of democracy and the whim of despots; fleecing the taxpayer…you get the picture. You know the stakes.
So we do the best we can with the tools we have. We attempt to build in future risk management for events we can’t possibly predict. This approach has been the status quo solution for decades. And this works. Until it doesn’t.
This works until the next inevitable technological disruptor. This works until the next inevitable medical emergency. This works until the next inevitable market catastrophe.
So what do we do to ensure we have enough money in retirement, without going to a job until we’re 80, working for somebody else, not in control of how and where we live and work?
What we need is not a side hustle; what we need is an intentional strategy to engineer joyful income for the rest of our lives.
This is not to say we should abandon conventional wisdom and stop using the qualified tools and advice provided by retirement professionals. They have, after all, dedicated their careers to helping us have security in later life.
On the contrary, we should avail ourselves of all the knowledge and expertise we have available to us while also planning what the next phase of our working lives will look like.
The Existential Crisis
Back in my drinking days, I used to stop at the same bar on the way home from work every day. I needed hard liquor to grind off the sharp edges of the day.
There is an older woman who shows up every afternoon at 4:15. Early 80s, sensible gray Flowbee haircut, slight build, waxy complexion, glasses, the corners of her mouth permanently downturned. Red Pizza Hut Delivery tee shirt.
Almost every day the first story out of her mouth starts with “this asshole I was delivering to today…”
Her name is Joy. For real.
I don’t know her circumstances except she is single and struggling. I don’t know if her husband died or left her. I don’t know if she has any kids to help her. I just know she doesn’t have enough with social security to meet even the basic needs of her life.
I also know that she’s probably going to be starting a lot of her stories with “this asshole today…” until she is too weak to carry on. And then what?
These are the very real consequences we face if we don’t have a plan in place. Unless you are very obnoxiously rich, you will worry about outliving your money. You may struggle to make ends meet, and then be put up somewhere to die in the most cost-effective way possible.
This is the existential crisis we face.
Can you be 100% positive that your retirement strategy will cover 100% of your life? Because if not, you can end up kinda screwed. Like Joy.
This is the worst version of Groundhog Day ever. Instead of waking up as Phil Connors working toward a moral and spiritual epiphany, you rise every morning to a fiscal Sword of Damocles hanging over your head by a single horsehair.
There’s also the fact that after decades of working, we should be happy. We should find actual joy in our lives. Be useful. Make meaningful contributions. Make meaningful connections with other human beings.
This is especially true in the age of AI. Human connection is a commodity we cannot afford to lose. And we’re smart. We should have no trouble finding a way to foster meaningful relationships with like-minded people and make money while we’re doing it.
Arnold Schwarzenegger has had 3 major careers in one lifetime: world’s greatest bodybuilder, Hollywood leading man, Governor of California when (at the time) it was the world’s 8th largest economy.
And now he’s doing probably the most important work of his life: philanthropy. Pretty good role model.
Now, we may not have his celebrity status to draw upon, but we can think big about what we want to do in our midlife-plus years.
With our hard-earned wisdom, experience, and Gen X entrepreneurial spirit, we can have an outsized impact on like-minded people also looking for purpose and meaning in midlife-plus.
But we must start exploring and building now, before we find ourselves in an untenable crisis situation. This is not optional.
What About a Retirement Side Hustle?
While you’re working, you can think of your money like an estuary: a river that rises and falls with the tide, like the Thames. Money comes in; money goes out.
But when you retire, your money turns into a plain old river; it only flows out.
This may be the niggle at the back of your mind you don’t really want to examine. Once you retire, the clock starts on your money. You instantly become a fixed-income citizen.
Every decision becomes a financial one.
So it’s only logical to have a plan to maintain this estuary-like balance after retirement, right? And by this logic it makes sense to start doing something about it while you’re still working to avoid a post-retirement gap.
Enter the side hustle.
I get the concept. Something you do on the “side” to generate some additional income. And “hustle” makes it sound kinda cool (eye roll).
Let’s get this out of the way. I don’t like the term “side hustle.” To me it implies you’re playing fast and loose, and being generally unserious. If you are going to do anything outside of your normal vocation, then treat it like a serious business. We don’t have all the time in the world to mess around with “might work” here.
This may be a strange statement coming from someone who is currently using the side hustle mindset to fill a temporary financial gap not being covered by my full-time job. But the key term here is temporary. Working part-time in trying financial times serves an immediate need, but doesn’t provide any long-term fulfillment. In other words, I don’t care deeply about it.
Don’t get me wrong because for some, the side hustle can be a legitimate entry point into a solo digital business. If you treat it like an entrepreneurial endeavor and not a “life hack” or shortcut to easy money. Many of the strategies can produce successful results if you approach it like “this is a business model that might work if I commit, learn, and iterate.”
And while it’s true that some part-time side hustles grow into six-figure entrepreneurial ventures, the numbers are a little slippery when you break them down by who’s actually succeeding.
If the goal is to start something lucrative to eventually replace your full-time job, there are scads of enticing opportunities being hawked at every turn online.
Some common themes are:
· Self-Publishing
· Dropshipping
· Affiliate Sites
The main problem with the hype surrounding these opportunities is they operate according to the Power-Law Game. Simply put, this is a system where a few rare, outsized, outlier successes generate the vast majority of results, while most attempts underperform or fail altogether.
Let’s examine how this applies to the Amazon Self-Publishing “easy money” system.
What the ads proclaim:
“I make $10K/month publishing eBooks!”
“Passive income while I sleep!”
“Use AI to write – No experience needed!”
What the actual data shows:
80–85% of self-published authors earn less than $1,000/year
Roughly 1–2% earn $100,000+
Most books sell fewer than 100 copies in their lifetime
Let that sink in for a second.
The overwhelming majority of people who try this don’t even reach meaningful side income.
Put another way, if you’re in a room of 100 people and one of them is Jeff Bezos, the average annual income is multiple-billion dollars. But the reality is there’s only 1 billionaire and 99 chumps.
It would seem the people selling you their system to make effortless money are making their money by…selling you their “system.”
But here’s the real thing—
There’s something else to consider: how long do you want to grind at something in your midlife-plus years when this stage has the potential to be the best years yet?
The main reason a side hustle isn’t your best solution is because it’s probably not something you care deeply about. And if you don’t care deeply, you’re likely to abandon it through boredom or dissatisfaction.
Whether it’s to close a financial gap, or generate some fun money, the result is the same.
Trading your time for money.
There has to be something better.
The 10% Expertise Principle
Imagine you’re back in high school and you’re sitting with your friends having lunch in the commons. Excited chattery cacophony and dappled sunlight fill the spacious atrium. This is everybody’s respite from the daily grind of required knowledge you can’t possibly see yourself needing in the future.
You and your best friend are in the same English class right after lunch. They ask you a question that chills your soul…
“Are you ready for the test?”
Oh balls! It’s on The Great Gatsby and you haven’t even cracked the book.
“Uuuuggghhh!! Totally spaced it! Can you give me a rundown? I’ll owe ya big time…”
You can’t afford to fail, and I bet you’d pay good money to get that info.
That’s all anyone needs to be incredibly valuable to another person. If someone values what you have…some information, some wisdom, some skill you have taken the time to acquire…they will pay money for a shortcut to their desired result.
Think about how many shortcuts you’ve paid for over your lifetime.
You don’t need a degree or decades of experience to be valuable to another person. You only need to be about 10% ahead of them.
“We’re Outta Here!”
There is a movement happening right now among Gen Xers; a proactive push to remove themselves from the traditional workplace before the workplace discards them due to a number of frightening factors:
· You’re too old – ageism is such an easy prejudice to circumvent by eliminating your position
· You’re too expensive – you get what you pay for, but apparently paying for wisdom and real-world experience can’t coexist with shareholder value and operating margins
· You’re too human – the move to replace experts with AI – and the failure to foster a partnership between dirt-cheap AI and the expert to create a super-producer – is an egregiously shortsighted approach
A very conservative estimate of 55,000 jobs were eliminated and replaced by AI in 2025.
I’m not stating this to cause any pearl clutching or handwringing over Skynet. This is just a fact that exists in an ever-changing world.
And this is the environment in which older workers entering midlife-plus are taking their show on the road and building expertise-based solo businesses. This entrepreneurial movement removes the employer who can lay you off without notice and puts the power over your destiny back where it belongs: squarely in your hands.
You can certainly repurpose your expertise into a client-based solo business. You can make a bunch of money doing it. And if you like the work you do, then more power to you. Solid plan.
But what if you don’t want to do what you’re doing anymore?
Build Your Escape Hatch
For the last 4 years I’ve been leading a project at my university research job. It’s important work, I’m good at it, and I make decent money. But good god it has me looking for the escape hatch at least once a week.
Part of the existential crisis I mentioned before includes the horror of watching the moments of my life trickle away doing things I don’t want to do.
I got this job in my late 40s by creating an escape hatch out of the bar business and into the world of mechanical design. It was a smart move. But more importantly, it created a blueprint for me to replicate and build a portal into the next, and most meaningful, phase of my life. Midlife-plus.
I’ve been working to solve this problem for almost a decade now: not working until I’m 80 for someone else.
I’ve studied direct response copywriting and made some money doing it. I’ve worked on client-based and clientless solo business models.
I’m an educator at heart. I’ve enjoyed teaching and tutoring my whole life. I always want to shorten the runway to success for others who want the knowledge I’ve spent time and effort to learn and put into practice.
I want to share what I know with you as I continue working toward my goal of completely untethering myself from having an employer, because I want that for you, too.
And I want you to think about building it on something completely new. Something exciting to you. Something latent or undiscovered. Or maybe it’s a thing you characterize as “that would’ve been nice.” It still can be.
The problem for most people is they get stuck before they even get started. But there’s a blueprint for how to get there: to thoughtfully, intentionally, and efficiently construct your escape hatch into meaningful long-term, lifelong income. The key is to quickly discover your ideal business, perfect customer, and how you’ll connect.
It’s time to stop thinking about Retirement Planning and start thinking in terms of Longevity Planning. Remember, we have a whole new life phase not available to previous generations. At least it hasn’t been characterized as such.
Until now, living longer just meant you had longer to worry about running out of money.
That’s why I’m advocating for reinventing yourself, learning something new, and building a business on something you care deeply about. And inviting others along for the ride. They want to come too.
Out of the 8,000,000,000 people on the planet, you only need about 1000 fellow travelers who see the world through your particular lens to join you on the journey.
We can create so much more than just “money for living.” I want to make my best work and most meaningful contributions in midlife-plus, now that I know a lot more.
I believe you do, as well. We’re old enough to know what 25 years feels like. So we know what the next 25 years can be.
Whatever it is that you want to do and share with others, you only need to be a little bit further along. About 10% ahead. They’ll pay for what you know if you are earnest and honest and generous with your knowledge.
I can show you how to better connect with the people you want to help. Let’s make the next stage of our lives more meaningful than we ever thought possible. The world needs what you have.
What do you want to do – is it knitting, woodworking, hot-rodding, countertop gardening, music, rock climbing…?
Whatever it is, you need to start building your escape hatch now, so it’s established, vetted, and ready to scale when you’re ready to go through it.
This could be the moment you look back on as the moment everything changed for the better.
Pretty soon Gen X will start turning 65, and most of us won’t have enough money to stop working. But we’re not worried, because we’ve already started building our escape hatch into more meaningful work after we hit eject on our current situation.
For those who refuse to think about it until it’s almost too late, we’ll be there for them.
We’ll show them how to do it.