If you spend enough time around people planning for retirement, you start to notice a familiar pattern: they twist themselves into knots trying to perfect their spreadsheets. They’ll agonize over safe withdrawal rates and debate tiny tweaks to their asset allocation, convinced that if they can just model every scenario, they’ll unlock the secret to retiring safely.
It’s understandable. When we’re talking about decades of future spending, the stakes feel sky-high. But it leads many people into a kind of false precision—an attempt to spreadsheet away uncertainty. They’ll spend years optimizing formulas, adjusting inflation forecasts, and hunting down the magic combination of bonds, equities, and alternatives that will guarantee a smooth glide path into retirement.
Except there’s one problem: retirement is ultimately a leap of faith.
No matter how elegant your spreadsheet is, no matter how many Monte Carlo simulations you run, the truth is none of us knows how the future will unfold. We don’t know what the market will do. We don’t know what will happen to our health. We don’t know how long we’ll live or what unexpected expenses might appear. And we certainly can’t say with certainty that some devastating, unlikely, but theoretically possible catastrophe won’t wipe out our portfolio.
Is that probable? No. Is it common? Not at all. But it is possible, which means every retirement plan—no matter how carefully constructed—requires a degree of trust in the unknown. It asks you to step away from guaranteed income and into a world where you simply hope your investments behave the way history suggests they will.
That uncertainty makes people nervous. And it should. But it also opens the door to a much more grounded way of thinking about retirement, one that doesn’t rely entirely on the behavior of financial markets.
To see it, you need to look beyond investment capital and focus on something most people forget once they hit their financial independence number: human capital.
Investment capital is consumed the moment you deploy it. Put money into real estate, equities, or bonds, and that capital becomes tied up—it’s working, but it’s no longer liquid. If markets crash, that value may evaporate. Again, unlikely, but possible. Investments can be excellent tools, but they come with irreversible commitments and inherent risk.
Human capital works differently. Unlike investment capital, it doesn’t require starting money. It begins with you—your skills, your energy, your expertise, your willingness to show up and do something of value. You can begin with nothing and end up with something purely through action.
That’s the magic of human capital: nothing is consumed in its creation.
You don’t lose anything by using it. You don’t tie anything up. If you attempt a project, take on a consulting gig, or launch a small side hustle and it doesn’t work, you still have the same skills you started with. Human capital regenerates. It compounds through experience. It’s the only asset that becomes more valuable the more you use it.
So how does this connect to retirement?
Think about the psychological stress surrounding the question “Do I have enough?” For many people, that anxiety is rooted in the fear of their investments failing them at the worst possible time. They look at their nest egg and hope it lasts the rest of their life. But hope is not the most comfortable retirement plan.
If you want a portfolio of true diversification—not just across asset classes but across types of capital—you need at least a small stream of human capital.
This doesn’t mean working full-time. It doesn’t mean going back to your old job. And it doesn’t mean grinding through a second career. For most people, their existing skill set is enough to create a few hours each week of flexible, optional, low-stress income. A consulting project here, a short-term gig there, a handful of clients—or even an entirely new activity you enjoy.
Even a small drip of income from human capital makes retirement radically safer. Because unlike your portfolio, which is always exposed to macro forces outside your control, human capital is under your direct influence. If markets fall, your ability to generate a little income doesn’t evaporate with them. And once you’ve built the skill, you can return to it whenever you want.
The best part? You were already using human capital for decades. It’s what got you to retirement in the first place. You likely have far more of it left than you realize.
Which raises a different question: instead of spending years obsessing over the perfect asset allocation, what if the stronger strategy is simply to maintain or cultivate a small, optional source of human-capital income?
Not a job. Not a commitment. Just a modest, enjoyable way to convert your time and skills into a little money whenever you choose.
For someone who wants true peace of mind, this might be the most powerful form of diversification available. You’re no longer relying solely on whether stocks behave or whether your withdrawal rate was correct. You gain the ability to adapt. To flex. To respond to a bad market year by adding a little income instead of cutting spending. And to go right back to not working the moment you feel comfortable again.
In other words, human capital gives you an emotional buffer. It reduces the need for perfection in your spreadsheet because you no longer need your spreadsheet to carry the entire load.
You don’t need to optimize everything. You don’t need to hit some magic number. You just need the ability to pick up a bit of work if or when you want it.
If retirement is a leap of faith, human capital is the handrail.
So maybe the healthier, calmer, more resilient approach is to close the spreadsheet for a moment and reconsider the question entirely. Instead of chasing the perfect allocation or the perfect withdrawal rate, invest in yourself. Keep a small, flexible connection to the kind of work you enjoy or are naturally good at. A few hours a week can make the difference between financial stress and financial ease.
In a world where uncertainty is guaranteed, human capital might be the safest asset you own.
Did you catch this week’s episode of Earn & Invest (Click to listen)?





I really enjoyed reading your article! Your emphasis on the importance of seeing ourselves as our best asset really resonates with me. Thank you for encouraging us to shift our mindset—it’s refreshing to prioritize our personal growth alongside financial planning!
More great thoughts, thanks for sharing them Jordan.
I believe it's critical that people invest time into figuring out a values-aligned approach to income generation as part of getting over the spending fear that can come with FI.
I also think MANY people could be financially free earlier than they think by doing this alignment work. The "Boring Middle" could turn into the "Amazingly Aligned" phase rather than grinding out some of the best years of your life praying to the spreadsheet gods while doing work you despise.