Never Retire: I Haven’t Worked a 9-to-5 Office Job in 25 Years—Here’s What I’ve Learned
It took me years to truly figure out how to 'work from home'—and not let work take over my life
Twenty-five years ago, I had an inside sales job in a towering corporate skyscraper in San Francisco’s Financial District. That’s the last time I ever worked full-time, 9-to-5 in an office environment.
Over the last 25 years—let’s call it the second quarter of my life as I approach 50—I had to learn how to work from home. Transitioning to freelancing and working for myself, I still had to fight against a reality people don’t talk about much: being your own boss doesn’t automatically mean you have a good one. Without boundaries, you can end up creating the same toxic work environment you once wanted to escape—only this time, you’re the one enforcing it.
I still struggle with this.
In a minute, a couple of key things I learned over the years that I constantly remind myself of as I strive to work less now so I can work less longer as part of my vision to Never Retire.
But first—
Later this year, I am launching a new Substack called Friki de Bici (Bike Geek).
Details below. You can subscribe here for free.
In an effort to keep this new bike- and urban planning-focused newsletter free—and to ensure I have the time and resources to do everything I want to do with it—I have set up a link via the Stripe Payments platform where you can support my work. My livelihood as a freelance writer. Because this ain’t no side hustle.
I decided to do this after seeing several people on YouTube—particularly my favorite aviation creator, Noel Phillips (he’s good)—use platforms such as Patreon to help fund their ongoing endeavors.
The reality is that the type of work I do and plan to do with Friki de Bici requires money and time (which is money). Whatever you can send my way helps ensure I can get the job done and get it done well.
Please use this link to support at any amount you choose.
That’s me. Working from home. At my desk.
Right now, I have a lot of work. And—because I want to spend the afternoons and evenings with my wife as much as possible before she spends a good chunk of her days in a ceramics co-working space—I have been doing most of it in the morning hours.
At the moment, I am mostly doing a 3-to-5 hour morning work spurt. On some days, I add another 30-to-90 minutes in the afternoon.
The ideal looks like this and will take shape later this month—
A 2-to-4 hour morning work spurt.
A series of one to three, 1-to-3 hour work spurts spread out through the afternoon with the flexibility to do a little less/a little more as needed.
More freewheeling time doing what I really love. Going out and about, taking pictures, walking around, riding my bike and talking to people—(as I continue to learn Spanish)—for the Never Retire newsletter and the forthcoming Friki de Bici.
As I see and structure things, there are two types of work you do as a freelance writer (and maybe your line of work as well)—
The first two bullet points where you sit at a desk, kitchen table or coffee shop and work in a focused way on specific tasks. For me, it’s moving from one story or article to the next.
The third bullet point where you don’t count minutes and hours. I’m out experiencing life, doing natural, physical (exercise) even social (informal and formal) things I love to do that fall on a less-focused, but very meaningful work continuum. Just taking things in, having informal social interaction, taking pictures, getting to know Valencia and—eventually, with Friki de Bici—going on bike rides that I chronicle via writing and video and interviewing people about this city’s bike culture.
So, the actual work—the focused, task-oriented part—ends up amounting to 25-to-30 hours a week.
The less-focused, but still casually organized work doesn’t feel like actual work. And it cannot be measured. Because it doesn’t need to be. It’s the true passion part of the equation.
To finally arrive and stay at this sweet spot (most of the time), I have to regularly remind myself of two key things, culled from memories working in that corporate environment that was actually a boiler room in San Francisco.