What working retirement actually looks like
I want to tell you about a Monday morning that changed how I think about all of this.
Eighteen months into building my second income, I was sitting at my kitchen table at 8:30am. Coffee. Laptop. Two hours of work ahead of me — a client call at ten, some prep beforehand, and then the rest of the day mine.
My neighbor backed out of his driveway at exactly the time he does every weekday. Suit on. Jaw set. That expression people get when they're already somewhere else in their head before they've left the house.
I'd worn that expression for a long time. I recognised it.
THIS WEEK AT A GLANCE
★ The Feature — What a working retirement actually looks like, and why most people who build one say they wouldn't go back
⚡ Quick Win — Design your own ideal working week
💡 Opportunity Spotlight — The income model that funds the lifestyle
❝ Reader Story — What a former HR executive's Tuesday looks like now
★ THE FEATURE
What working retirement actually looks like — and why it's better than the original plan
Most of us grew up with one picture of retirement.
You work. You stop. You're done.
I want to suggest that picture — for most people reading this — isn't just unrealistic. It's also not what you actually want.
What most of us are really after isn't the absence of work. It's the absence of work we don't control.
There's a difference. A significant one.
The people I know who've built what I'd call a working retirement — earning meaningful income on their own terms, from their own knowledge, on a schedule they control — don't describe it as work the way they used to describe work.
They describe it as engagement. Purpose. The thing that makes the rest of the day feel earned.
Margaret, from Issue Nine, works about twelve hours a week on her curriculum consulting. She told me she couldn't imagine stopping entirely — not because she needs the $2,100 a month, but because the work keeps her connected to something she cares about.
Robert, from Issue Ten, takes Fridays off. He's thinking about Thursdays too. He decides. That's the point.
What does it look like day to day?
The mornings are theirs. The real work — client calls, thinking, delivery — happens in a few concentrated hours. The afternoons look different from what they used to.
The calendar is theirs. Clients have schedules too, but the days of three back-to-back calls because someone else decided that are largely gone.
The work is chosen. Gradually, as the practice grows, you decide which clients you work with and which problems interest you. That selectivity is something most people haven't had since the start of their careers — if ever.
And the income, while more modest than a full-time salary, is often more than enough when you factor in what goes away. No commute. No office wardrobe. No parking. The cost of going to work was a number most people never calculated. When you're working from your kitchen table ten hours a week, it goes to zero.
It doesn't look like the retirement we were sold.
It looks better.
⚡ QUICK WIN
Design your ideal working week — right now
Do this before you have the practice built. The clearer the picture, the more real it becomes.
- How many hours a week would you want to spend on client work? Most people land between eight and fifteen.
- Which days and times? Morning person? Never Fridays? Write it down.
- What does the rest of the time look like — specifically? Travel, grandchildren, a project you've been deferring for years?
- How much monthly income would make that picture financially sustainable?
In most cases, that number is achievable with two to three consulting clients at reasonable rates. You've just described what you're building toward.
Keep it somewhere visible.
💡 OPPORTUNITY SPOTLIGHT
The income model that funds the lifestyle
Two to three retainer clients at $1,200 to $2,000 a month generates $2,400 to $6,000 a month from ten to twenty hours of weekly work.
That covers the retirement income gap for most people in this community — and funds the lifestyle described above.
The people building this aren't waiting for perfect conditions. They're starting with one offer, one conversation, one client — and building the picture one piece at a time.
If you're ready to explore what this looks like for your specific background, there are programmes built specifically for experienced professionals at this stage — people who know what they have to offer but want a structured path to turning it into a sustainable practice.
I'll be sharing more detail on what's available in the next issue. But if you don't want to wait, hit reply with a brief description of your professional background and where you are in the process. I read every response, and I'm happy to point you toward the right starting point.
CLOSING SIGN-OFF
The working retirement most people in this community are building doesn't look like what we were told to want. It's quieter. More chosen. More yours.
And it's more achievable than most people realise — not at some distant point, but from where you're standing right now.
If you're thinking seriously about building this, now is a good time to look at what's available to help you get there faster. Reply with your background and where you are in the process — I'll point you in the right direction here.
Until then,
Richard
