The Beginning Often Looks Unimpressive

At 56 years old I’m preparing to hike to the bottom of the Grand Canyon one more time before my left knee is total shit.

But you don’t train to hike the Grand Canyon by hiking in the Grand Canyon.

Before I hit the canyon trails, there needs to be a period of preparation. Yes, that means preparing my body for the physical assault I plan to perpetrate on it. But also, I need to study and prepare for the specific challenges, both physically and mentally, I will face.

This includes:

• Which trail to hike – the Bright Angel Trail is a very different experience than the South Kaibab Trail

• What time of year – temperature is a big factor on stamina, especially in the afternoon

• Day hike or camping – hiking down to the Colorado and back up in a single day (as opposed to reserving overnight camping inside the canyon) exposes you to the most heat when you are at your most fatigued on ascent

• Water availability – some trails have water stations, others do not – that means packing extra water, and water is heavy

You get it. These aren’t secret ingredients. It’s not mind-blowing that preparation and training are essential to achieving a preferred outcome. This is not a piece about hiking, either.

It’s about midlife reinvention, and how we approach entering Midlife-Plus by starting our own solo business.

At midlife we are wiser than we’ve ever been, and getting wiser with every passing year. (I assert that if we’re actively engaging with aging our wisdom grows exponentially.) We know preparation is necessary, but the real key is how we conceptualize and approach this new phase of our lives.

People often imagine transformation as one dramatic act:

• quitting the job

• launching the business

• hiking the canyon

But the real battle is usually much less cinematic. It’s the phase where you are still fundamentally the same person…

…but you begin acting against the inertia of your old life.

Surely you’re familiar with the Western interpretation of Lao Tzu’s proverb from the foundational Taoist text, the Tao Te Ching:

The journey of a thousand miles begins with a single step.

In Western culture, the phrase is heavily used as a motivational slogan to overcome procrastination and tackle intimidating, long-term goals.

But I’m thinking about it here as a means to just get moving, and the path will become clear as you accumulate steps. In the early stage of transformation, movement matters more than motivation.

(A purer translation is that the long journey “begins beneath your feet,” which is about being present in the moment and mindful of the immensity of the task you are preparing to undertake – this works here as well)

You learn along the way what works and what doesn’t. And you do more of what works and remove what doesn’t. Lather, rinse, repeat. Simple as that. And along the way your motivation becomes clearer as well.

What started as:

“I want to start my own solo business to protect myself from being downsized”

may become:

“I am starting my own business because I want to evolve into something new in the one-and-only life I get.”

So here’s the thing many of us fail to consider at the outset: the early stages of transformation often look unimpressive from the outside.

Repetition. Fatigue. Tiny progress.

But that’s how inertia breaks.

Breaking Inertia

I worked a grueling job collecting garbage door-to-door at apartment complexes at night. 5 hours up 3 flights and back down, carrying a bag as tall as me, filled with 60 pounds of other people’s garbage.

Not because it was satisfying.

Not because it was inspiring.

I did it because movement mattered more than inspiration.

Motivation doesn’t happen because of some “inspiring” quote painted in cursive on a piece of distressed faux driftwood from some hobby shop. It happens because you take action and start moving.

We can end up waiting indefinitely to be motivated by the right message of inspiration. All this amounts to is procrastination. And this flavor of procrastination is a result of a fear of failing.

So why garbage? There are plenty of ways to jump-start a canyon-hiking prep regimen, like going to Austin High and running bleachers. But there was something appealing to my blue-collar romanticism in this gritty training montage. And you don’t get paid to run bleachers.

Every time I dragged my ass up from a nap to go to this job (this was a second job in addition to my full-time, btw), I groaned and bitched and moaned. Still, I had made a commitment to Valet Living and I was expected to show up.

From the outside, it probably looked irrational: physically exhausting, unglamorous, unsustainable.

Internally, it was something much more important: proof that I was willing to begin.

But once I start my evening, on the first 3-story flight of the night, I feel the power of iteration accumulating towards my goal, and I imagine the hike that will get me to the canyon’s inner rim, the mighty Colorado thundering half a mile below, to watch the magnificent sun set into the western end of the gorge, slowly chased to the horizon by a darkening purple sky.

We underestimate lifestyle and social inertia because it’s invisible, and by midlife, this inertia is powerful. Your routines have calcified and your identity is hardened, carved by decades of responsibility. As your obligations multiply, you realize how finite your energy is.

This is the moment it becomes more imperative than ever to shake yourself loose and start thinking about the next phase of your life. How will you choose to take control of it?

The first breakthrough isn’t inspiration. It’s motion.

The first victory isn’t success. It’s disrupting the pattern.

You Build Capacity Before You Need It

(get ready for some lists so we can get through a lot real fast!)

Nobody wakes up ready to hike the Grand Canyon at 56. You build the capacity slowly, long before the descent begins.

And the same thing happens in business.

Before:

• confidence

• income

• momentum

• identity change

There’s usually a quieter stage:

• awkward effort

• inconsistent progress

• fatigue

• uncertainty

• repetition

The early phase is less about results than adaptation. You’re teaching yourself “I am still capable of becoming someone new.”

That’s the real transformation.

And I get it. We’re exhausted at times, and relaxation and recharge are requirements of a sane life. Most “start a business” advice accidentally creates more inertial resistance, keeping you stuck.

What you don’t need is more advice on:

• Branding

• Funnels

• Websites

• Niche selection

• Monetization models

• Content strategies

Don’t discount the importance of any of this. All of this is important and necessary to effectively build a successful solo business. But don’t put the cart before the horse.

What you do need first is to:

• Rebuild adaptability

• Reconnect with curiosity

• Develop self-trust

• Accumulate small proofs of capability

Even though we need to develop a mindset of becoming entrepreneurs, we don’t need all the added pressure of “becoming entrepreneurs,” at least not at the beginning of the process. What we need are small acts of capability-building that quietly reawaken our agency.

I mentioned above that we need to reconnect with our curiosity. But...how?

Try performing a quick “Curiosity Audit” and get some quick insight into what gets you excited. Ask yourself some questions like the ones below, and jot down some thoughts.

• What subjects make you lose track of time? (doom-scrolling doesn’t count!)

• What problems do you naturally research?

• What conversations energize you instead of drain you?

• What did you abandon because it seemed impractical?

So often our curiosity gets suppressed by seemingly endless obligations. But when it comes to discovering what you want to base a solo entrepreneurial venture on, curiosity is frequently the trailhead (see what I did there?) to meaningful work.

The Psychological Shift We’re Really Talking About

Just like you don’t train for hiking the canyon in the canyon, you don’t start a solo business by quitting your job.

• Commitment to a new thing is not a dramatic, performative gesture

• You build capability to be prepared for crisis. - so you certainly don’t want to create crisis before you build capability

There’s an old motivational phrase about taking time off work that is some variation of:

“When you get to the end of your life, are you going to be glad you didn’t take off work that day to go to that [special thing]?”

So when it comes to building your escape hatch out of a job you can’t stand, are you going to look back and be glad you didn’t explore starting something new? Are you going to be happy you decided to grind away to 80?

Inertia-Breaking Action Steps

These are the steps I took initially to prioritize movement over inspiration. You don’t need a clear path to an end goal. You only need to start moving, consistently repeat the movements, and clarity will emerge gradually.

• Write 50 words a day – EVERY day

  • What does your ideal life at 70 look like?

  • What are you wanting ‘tomorrow’ that you don’t have ‘today’?

• Read a book!! (I recommend reading Simon Sinek at least twice during your transformative phase; it hits different each time)

  • Start With Why – Simon Sinek

  • Be Useful – Arnold Schwarzenegger

To your continued growth.

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At 43 years old I went back to school to supplement my B.A. in English Lit with a more useful Associate of Applied Sciences degree. I made a decision to carve a path to get out of the bar management business. I was chafing at the prospect of continuing into my late 40s and 50s babysitting drunk adult children.

Within 5 years I completed a 2-year degree and secured a mechanical design job at a university research laboratory.

I had carefully and successfully crafted an escape hatch from a figurative (and potentially literal) dead-end, and emerged into a world of new possibility.

Now, there’s really nothing remarkable about career pivoting in my 40s, so don’t be alarmed that I’m climbing up on a pedestal here. An action like this is practically mandatory for Gen X. Gone are the days of companies taking care of their employees with generous pensions; gone too the employee loyalty that resulted from those pensions.

What I found particularly interesting were the effects this had in other areas of my life.

I experienced an emotional transformation through divorce.

I experienced physical, psychological, and spiritual transformation on my journey to sobriety.

It would seem that by taking positive action to transform one aspect of my life, I was left no choice but to evaluate the full spectrum of my existential condition.

This was the real “light bulb” moment for me: it wasn’t about just changing what I was doing vocationally that led to a more satisfying life. I was experiencing a whole mindset shift and evolving into the next, and more gratifying phase of my life.

What I was really doing was establishing a repeatable blueprint that now serves as the basis for how I approach the next logical move into an even more meaningful stage of life: Midlife-Plus.

This is the period from our 50s to our 70s in which we can do something completely new.

Midlife Stagnation Isn’t Real

In 1958 Alfred Hitchcock, in his psychological thriller Vertigo, popularized the filming technique of the dolly zoom, also known as the “Vertigo Effect.” He used this “dolly-out/zoom-in” technique to capture the dizzying discombobulation experienced by James Stewart’s character looking down the bell tower shaft.

This dolly zoom technique has been utilized over the years to great effect. Like when Roy Scheider sees the shark for the first time in Jaws, or when government agents are looking over the hill down on Elliott’s neighborhood in E.T the Extra Terrestrial.

But my particular favorite use of the technique is in horror movies when it’s used to make the end of a hallway stretch away in the distance, the door at the end retreating, seemingly unreachable, as the victim tries to outrun the pursuer.

This is exactly how many Gen Xers feel about the retirement goal line…forever retreating into the future.

Why is that?

So many reasons. But chief among them:

1. No more pensions – as mentioned above. The late 1970s saw the corporate pension replaced by the 401k plan – secure lifetime income was replaced by a savings vehicle especially sensitive to market volatility.

2. The longevity factor – people are living longer. We’re already watching wide-eyed baby boomer retirees fret about outliving their money. Gen X may have to work well into their 70s and possibly 80s to feel secure enough to stop working.

3. Traditional retirement is dead – your parents’ model of “learn, earn, retire” that served them well (to a point) is no longer valid in a world that has dramatically changed. It’s a classic square-peg-round-hole conundrum.

And there’s another factor to consider as well, the unpredictable unknown: AI as the fourth industrial revolution.

Given the state of rapidly changing technological advancements with AI, and the pressure companies are under from share stakeholders to reduce operating margins, there’s no telling at what point the older, expensive, experienced knowledge worker will get the axe.

Let’s not get too overly dramatic about the robot uprising, but there should still be a sense of urgency to finding a better solution than traditional retirement.

The feeling of midlife stagnation is less of a dramatic collapse, and more of a slow erosion of time.

The day will come, if it hasn’t already, when you’ll quizzically furrow your brow and think “man…I thought for sure I’d be further along by now.” In all likelihood this disconnect can be traced back to our twenties. We were presented with the status quo idea of retirement as something to look forward to eventually, and probably didn’t give it much more thought at the time.

It’s really no surprise that we arrived in our fifties and realized that this way of thinking wasn’t going to work as advertised. We’re not to blame for thinking that the way it’s been done is the way we should do it too.

But the reality is we are not locked in to a particular way of approaching this problem. We don’t have to try and adapt a broken model to fit our circumstances. We can build a whole new model for how to enter our midlife-plus years.

So, what’s the alternative?

Unstick Your Thinking

Just because you haven’t thought about an alternative to retirement yet doesn’t mean you’re too late. But it is paramount to start exploring your options now.

The writing has been on the wall for some time. Especially if you waited like I did to do any serious retirement saving.

It may seem like the only option is to keep doing what you’re doing, saving as much as you can for as long as you need to, and finally calling it quits when it seems like you’ll be safe.

But what if you hate what you’re doing and can’t imagine doing it for another 25 years? Will the goal of retirement ever arrive?

Maybe. But maybe not. Maybe we’re wrong to assume retirement is a goal to be reached.

What if we approach our midlife-plus years as a whole new phase to do something new and exciting? We can use a lifetime of experience and wisdom to make money in ways that don’t involve going to a job, working for someone else, not in control of how and where we live and work.

Retirement can just be a moment we stop doing one thing and start doing another, more important and more satisfying thing.

The really good news is, if you STOP thinking of retirement as a terminal event, and rather a door you engineer into a more meaningful life making joyful income, the perspective changes.

Instead of retirement as a moving finish line, it becomes a simple list of things to check off before you step through the portal you create.

Start Creating the Escape Hatch

When you know you don’t have enough to retire because you started too late, despair can percolate just below the surface at a constant simmer. You can feel like circumstances are controlling you instead of the other way around.

Instead of working for 25 more years at a job that holds you down, build a business around what you want to do instead. You can take control and regain your agency.

Plan on starting your own solo business around something that excites you. Then pay attention to how many other aspects of your life come into focus.

You will begin to feel more in control of the direction your life moves. You’ll start reclaiming agency and regaining control.

The “business” component is simply the mechanism for regaining control.

Try this little thought exercise to get the business ideas rolling when you’re out walking the dog or whatever:

My Solo Midlife Business is…

Client-Based – “Here, let me do that for you. I can do it better anyway!”

-OR-

Course-Based – “Here, let me show you how to do it so you’ll go away and leave me alone!”

This is greatly over-simplified, and it’s not really a binary choice, but it’s a really snarky Gen X way to think about it.

So let’s get to it. It’s up to us!

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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 8^th 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.