Your Yellow Brick Road to Retirement
The moment you receive your first paycheck you’ve started along that yellow brick road toward the retirement. That was so many years ago for some of us, we may have forgotten this, but retirement represents the destination many of us are trying to get to: living independent of the need to work. You spend years saving, thinking of that distant time. But in the years and months prior to retirement, we are confronted with a hurricane of decisions that come with the prospective change.
Among them:
- What will I do when I no longer have to work to support myself?
- How will I occupy my time?
- Will I miss the workaday world I’m living in?
- How will I stay social? Keep engaging my brain?
- If before 65, what will I do about health insurance?
And…. the big one:
- Do I have enough money to do all this?
You’ve scrimped and saved to get to this point. You’ve gone down that yellow brick road for awhile, but ultimately you’re not sure where you’re going or where the road leads. You can’t see the future, after all. Your friends may even have recommended that you might consider using a financial advisor to get more information about how to get to retirement… So you’re off to see the Wizard.
The Wizard Behind the Curtain
We all know what happens in the Wizard of Oz- toto pulls that curtain back and we see that behind all the fire and thunder and intimidating machinery, the vaunted Wizard is just an old dude pulling some levers. Total letdown.
Let me be fair: not every financial advisor is the Wizard. Some are genuinely excellent, and for complex situations — business owners, significant estates, multi-generational planning — professional guidance is worth real money. I’m a fan of fee-only financial advisors. We often need this confirmatory step in our planning.
But the industry has built a culture of mystification that doesn’t serve most people.
The language is deliberately complex. The tools are locked behind expensive software or paywalls. The standard fee — 1% of assets under management annually — means that on a $800,000 portfolio, you’re paying $8,000 a year. Every year. Whether the advice took ten hours or ten minutes. Whether the market went up or down.
Behind the curtain is a person entering your information, pulling a lever of a Monte Carlo simulation, applying rules of thumb you could read about for free, giving you recommendations that in many cases you could have reached on your own.
I’m not saying the Wizard is malicious. I’m saying the curtain isn’t necessary. Why can’t we – those of use who have an interest in the numbers but not access to the tools – “Do-it-Yourself” (DIY) and use similar tools to chart our own journey?
A DIY retiree is someone who is traveling their own yellow brick road and finding their own answers. I hope that DIY Retiree can help you down the road.
“What’s your Wizard of Oz Financial Personality”?
(a totally made up thing I just made up cuz you know, clickbait.)
Dorothy picks up three companions along the way, and many of us fall into one of these stereotypes. Which “Financial Wizard” personality type are you?
The Scarecrow is the person who thinks they’re not smart enough to manage their own retirement. Successful career, smart about everything else in their life, goes completely blank when someone says “sequence of returns risk” or “4% rule.” They assume finance requires a special kind of intelligence they simply don’t have, or worse, they have the facility but choose not to.
Money isn’t that hard, tbh, and the mystique of the financial planning industry perpetuates this. The concepts aren’t complicated — but they use unfamiliar vocabulary. Once you learn the words, the math is mostly arithmetic. The Scarecrow devised the plan to rescue Dorothy from the witch’s castle. He had a brain the whole time. He just needed belief in himself to use it.
The Tin Man is the person who got burned. Maybe 2008. Maybe a financial advisor who churned their account. Maybe just watching their portfolio get cut in half during a crash and making some decisions they’re not proud of. They’ve kept their money somewhere safe and quiet ever since, earning almost nothing, while inflation quietly does its work.
There’s no judgment there — the fear is real. But fear managed poorly is its own kind of risk. The Tin Man’s heart was never gone. He just stopped trusting it. Most people who have achieved financial success had some problems along the road, or what’s a journey for?
The Cowardly Lion knows exactly what they should be doing but hasn’t quite done it yet. They’ve read the articles. They understand the concepts. They’ve been meaning to sit down and run the actual numbers for months, maybe longer. But the stakes feel too high to risk getting it wrong, so they don’t start. When they look at the numbers, fear of the unknown sets in (hint: some of retirement planning is unknowable!) so they shut down.
I’ve definitely been in this camp. I have an MBA and have looked at excel spreadsheets for years, but planning my OWN retirement is daunting, and dare I say… Confusing? I mean, IRMAA surcharges? <sobs in Cowardly Lion>
That’s why, for instance, we have an IRMAA surcharge calculator.
The thing that helped my paralysis was finding and developing good tools. This made abstract concepts concrete.
Run your numbers through a Monte Carlo simulator and suddenly you’re not staring at a scary unknown. It’s empowering. You’re looking at a probability. You can work with a probability.
Glinda Was There the Whole Time
Glinda knew about the ruby slippers from the beginning. She knew Dorothy had the power to go home. But she also knew Dorothy wouldn’t have believed it without earning the understanding herself — without the yellow brick road, without the companions, without going through it.
(Or it was a plot device, but then the analogy falls apart.)
The tools to plan your own retirement have always existed. For decades they lived behind the curtains of professional planning software, accessible only to advisors who charged you for the access. That’s changing fast. The knowledge is out there. Calculators that used to cost thousands of dollars in software licenses are being built in the open, for free.
What was missing was someone to point at the ruby slippers and say: those are yours.
Your Ruby Slippers as a DIY Retiree
A DIY Retiree is someone who has pulled back the curtain.
Not someone who thinks retirement planning is easy, or that the decisions don’t matter, or that you can’t make costly mistakes — because you can. But a DIY Retiree is someone who believes they are capable of understanding their own situation well enough to manage it. Someone with the curiosity to learn, the discipline to follow through, and the willingness to engage with the actual numbers.
On this site you’ll find a Monte Carlo retirement simulator that runs 2,000 scenarios against your specific numbers — the same analysis a planner would charge you hundreds (even thousands) of dollars to produce. You’ll also find
- A SimpliFI early retirement calculator
- An IRMAA surcharge calculator
- A calculator to help you decide whether ‘one more year’ is worth it
You’ll also find plain-language explanations of the concepts that actually matter: sequence of returns risk, safe withdrawal rates, the retirement smile spending, the 4% rule.
No paywall. No subscription. No wizard.
Dorothy’s ruby slippers were on her feet the whole time.
The power to get home — to build the retirement you actually want — was never somewhere else. The journey matters. The companions help. But the magic? That was always yours.
As a fellow retirement blogger put it to me this week: “We are ALL DIY Retirees.”
Do the work. Run the tools.
*Click your heels*
Tony Markey, MBA, founded DIY Retiree to provide free retirement planning tools and straight-talk guidance for pre-retirees managing their own financial futures. Read more about his story here