The 20-Year Audit: 13 Questions for Anyone Over 50 With a "One Day" List

Waiting won't make you readier, just older. A working exercise for taking your next two decades seriously.

My daughter Cerys has just spent four weeks with us: 2 in Vegas, 2 in Cabo.

Last week she flew back to London 😢, and shortly she’s off to Paris with her friends to celebrate her 20th birthday, because at 20, Paris with your mates beats Cabo with your parents right?

20 years old. 😳

Which means twenty years ago I didn’t have a child. I hadn’t met Rhett. I didn’t know what an online business was, I hadn’t started travelling, and I was living a completely different life in a different country, doing work I can now barely remember doing.

If you’d shown that woman a photo of me today, writing this from Vancouver while Rhett conducts his daily audit of the room temperature, she’d have thought - a) jeez dye those grey hairs Jo, and b) - wow that was a crazy ride!

20 years, gone in what feels like a long afternoon.

We’re Not Getting Any Younger

Here’s the cheerful part. Every year that passes, statistically, we have slightly less runway ahead of us than behind. I’m not being morbid; it’s just maths, and maths doesn’t care how morbid that is.

I’m 53. If the actuarial tables are in a good mood, I’ve got 30 decent years left. Maybe 40 if I keep up the walking and go easier on the margaritas, which, having just spent two weeks in Cabo, I can confirm I have not. 🍸🤭

You know your rough number too. We all do, even if we keep it filed in the same mental drawer as the pension paperwork.

How much time you have is largely out of your hands. What you do with it, though, is wide open.

Look Back 20 Years. Then Look Forward 20.

Where were you 20 years ago? What city, what job, what people around your kitchen table? What did your average Tuesday look like, and what were you worrying about that turned out not to matter at all?

I’d bet you can barely recognise that person.

Twenty years is enormous: whole marriages happen inside it, along with whole careers, whole houses bought and sold and bought again, whole children raised from newborn to adult and released into Paris with their friends. In our case, whole countries are explored and lived in.

You’ve likely done far more with the last 20 years than you give yourself credit for.

Now turn it round. If things go reasonably well, you get to do all of that again: another 20 years of a life you can barely predict from where you’re sitting today.

The only real question is whether the version of you at the end of them, looking back at today, thinks you made decent use of the time.

You’ll Never Be Ready

I didn’t feel ready when Rhett and I moved the family to Cyprus in 2010, with a four-year-old, no plan, and a recession chewing through our income. We went anyway.

I didn’t feel ready when we started our first online business. I had no idea what I was doing. Neither did Rhett, although he had plenty of opinions about it, which at the time we both mistook for expertise. We figured it out.

I didn’t feel ready when we finally took to the road in February and became full-time nomads at 53 and 49. Five months and three countries later, I’m writing this from Vancouver, Rhett’s now 50, and we’re still working out what this life is.

I didn’t feel ready when I started this Substack, I don’t feel ready to publish my book, I won’t feel ready to start making YouTube videos, or to launch the next stage of This Big World, or to tackle most of what’s sitting on my one day list.

But I will do them all anyway.

Because here’s what I now know at my age: you don’t get more ready. The moment doesn’t arrive, the window doesn’t widen, the savings don’t build fast enough, and the plan never clarifies itself into a shape you can act on.

Waiting doesn’t make you readier. It just makes you older.

Your Age Is Fuel. Use It.

When you’re 20 you can afford to be gung-ho, because you’ve got 60 years to clean up after yourself.

At 45, 55, 65, you don’t have that luxury. But what you do have instead is better!

Because you have knowledge, pattern recognition, mistakes already made and paid for, resilience already built, and a well-worn “I’ve survived worse than this” muscle that only comes with time.

You know things now that the 20-year-old version of you couldn’t have imagined. What matters and what doesn’t. What you’re capable of. Who to trust. What deserves your fear and what you can walk straight past.

That’s your unfair advantage, and every day you don’t use it is a day it sits in the garage under a dust sheet.

So Let’s Do Something With This

Reading this and nodding along is the easy part. But don’t just sigh, close the tab and go back to your ‘one day’ list.

Let’s take massive action!

Below is an exercise I recommend you sit down and do in full: The 20-Year Audit.

And if 20 years feels like the wrong horizon from where you’re sitting, make it 10, or 5, or 30. The number matters far less than the honesty.

3 sections, 13 questions, about an hour of honest reflection. Get out a notebook and a decent pen, find a quiet corner, and turn your phone off.

It's too easy to muse on what life could look like. ‘One day’ stays a daydream right up until you write down what it is, when it starts, and what's been stopping you. This is that exercise.

NB: If you’d rather work on paper, I’ve turned the whole thing into a printable PDF: you’ll find the download at the bottom of this post.

No paywall on this one, but if you do join The 50+ Nomad, you get full access to The Backpack resource library ($500+ value). All my courses and guides on building location independent income, becoming a nomad or frequent traveller, and living your best life in your 50s & beyond!

To celebrate my husband Rhett’s 50th birthday, annual membership is 50% off throughout July. 🎉

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The 20-Year Audit

A framework for taking your next two decades seriously.

Answer honestly: this isn’t for anyone but you, and the questions are deliberately uncomfortable to make you dig deep so you feel emotionally attached to your future plans.

Part 1: Look Back — Where Have You Been?

1. Where were you 20 years ago?

Be specific: what city, what home, what job, what relationships? Reconstruct that year in as much texture as you can manage. Vague answers produce vague insights.

2. What did you spend most of your days doing?

Work, family, hobbies, worries, routines. The shape of your average Tuesday, 20 years back.

3. What did that version of you think you’d have achieved by now?

Career, family, financial, personal. What was on the mental list?

4. What have you done with those 20 years in reality?

Count everything, including the things you think are irrelevant: the family you raised, the relationships you kept alive, the losses you survived, the person you became.

5. What did you almost do 20 years ago (or along the way) that you didn’t?

The move you nearly made. The business you nearly started. The relationship you nearly left or nearly began. The version of your life you almost picked instead of the one you got.

6. What would 20-years-ago you say about you now?

Proud? Confused? Relieved? Disappointed? Sit with the honest answer, whatever it turns out to be.

Part 2: Look At Now — Where Are You Standing?

7. What are you currently telling yourself you’ll do ‘one day’?

Write all of it down. The book, the business, the move, the pivot, the learning, the thing you don’t say out loud. Every single one goes on the page.

8. What would need to be true for you to start any of them this year?

Be specific. Money? Time? Permission? A push? Someone to do it with? Name the real truth, and dig deeper if it sounds vague.

9. What are you afraid of, really?

Being seen wanting more. Failing publicly. Succeeding and having to sustain it. Being judged. Being wrong. Name the one you don’t say out loud to anyone. No one has to ever see this but you.

10. What is it costing you to keep waiting?

In money, yes. But also in energy, in confidence, in relationships, in the version of yourself you’re becoming while you postpone. What does another year of one day honestly cost?

Part 3: Look Forward — Which Version Gets Written?

11. What does life look like in 20 years if you don’t go for it?

This is a hard one, so don’t rush it. The book stays unwritten, the business unstarted, the move never made. Same routines, same one day list, twenty years older.

Who did you spend those years watching do the things you wanted to do?

And what did the people watching you, (your children, your grandchildren, your friends), learn from you about what’s possible after 50 (60,70)?

Sit with that version for a while. How does it feel?

12. And what does life look like in 20 years if you do go for it?

Same 20 years, other path. What have you built? Who have you become? What stories do you have that you don’t have now?

What do the people who love you say about you, and what did you show them was possible at 50, 60, 70?

What’s the legacy: the money, the work, the example, the proof that it wasn’t too late? Write this one in as much detail as the last one (if not more. You need both pictures side by side.)

Now sit with that version for a while. How does it feel?

13. Which of those two versions are you going to write into being?

One of them is coming either way; the 20 years pass at the same speed whether you use them or not. If your answer is the second version, the follow-up is simple: what one thing are you going to do in the next 30 days to start it?

What To Do Next

Answer all 13 in one sitting if you can, and don’t worry about being tidy or profound. Honest beats both.

When you’re done, do three things:

1. Circle the one thing on your ‘one day’ list you'd regret most if you never did it. That's your big goal for the next 20 years. Your BHAG. (Big Hairy Audacious Goal)

2. Underline the answer that explains why you haven't started it yet. It's probably sitting in question 9 or 10. That's your obstacle, and it has far less power now you’ve named it.

3. Write down one small action you can take this week towards your BHAG. Not the whole plan. Just one action this week - obstacle be damned.

Then put the notebook somewhere you can keep reading and reviewing. In six months, do the whole thing again and see how the answers have shifted, what you’ve started, and what you’ve stopped telling yourself.

Wherever you're standing right now, the last twenty years put you there. The good news is that the next twenty are yours to point in any direction you like.

So let’s make them our best years yet! 🥳

Jo 😊