Run the Sprint on Yourself: What a Former Coworker Taught Me About Applying Agile Thinking to Your Own Career

Years ago I worked with a guy named Jim. His team ran the way a lot of teams do now — sprints, standups, a shared board everyone could see. One person on the team, Mike, kept a personal kanban board going for his own side projects. He was a big early adopter and advocate for applying agile thinking outside of work, not just inside it. Jim watched all of that happen right next to him. It didn’t occur to him to do the same thing for himself. Not yet.

Life moved. Jim changed companies. For a couple of years I wasn’t doing much outreach at all, and we lost touch.

Later I started a newsletter. One issue took a play straight out of the playbooks of modern employers: what would happen if you used agile and lean management practices on your own life and your most important personal projects, the same way you use them at work? Most people leave work at work — even people who spend years, and tens or hundreds of thousands of dollars, training themselves for it. They sell their employer their best technical and management thinking at a high return to the company, and never once turn that same thinking back on their own life.

Jim called me later to say he’d never thought about it that way.

He didn’t act on it right away. But a while after that, when I followed up, that was the moment. He became a client.

Here’s what happened once he actually did it — once he pointed the same thinking at himself that he’d been running at work the whole time. He’d had a goal sitting on a five-to-ten year timeline: buying a beach condo. Once he had a real plan and was working it the way he’d work any other project, that timeline collapsed to one year. His income grew right along with it. When I asked him what made the difference, his answer was blunt:

That’s the whole idea I want to draw out here.

You Already Know How to Do This. You Just Don’t Do It for Yourself.

Here’s the pattern behind Jim’s story, and it’s the reason I built this into my coaching programs as an actual skillset, not just a metaphor.

You wouldn’t run a team project by picking a direction once and never checking on it again for a year. You wouldn’t skip every check-in and just hope it worked out. You wouldn’t refuse to prioritize and try to do everything at once. But that’s exactly how most people run their own careers.

Most of my clients don’t run agile teams for a living. But a lot of them have been near it — sat in the meetings, seen the board, heard the language — even if, like Jim before that newsletter issue, they never thought of it as something they could point at themselves. Agile itself stopped being a software-only thing a long time ago. The industry’s longest-running survey on it, Digital.ai’s State of Agile Report, has tracked it spreading well past IT departments into HR, marketing, and other business functions for several years running.^[1] So let’s actually translate it.

What This Looks Like When You Point It at Your Own Life

Design thinking. In plain terms: figure out what’s actually wrong, and what actually matters, before you jump to a fix. Most people skip this. They decide they need a new job title, or a raise, or a total reinvention, without ever slowing down to find out what’s really driving the dissatisfaction. Two things handle this together in my coaching work: the Alignment Audit, which I’m giving away right now inside Skool and elsewhere — the same listening-first work a product team does before they build anything, except the product is your own next move — and the Infinite Focus Blueprint, which takes everything the audit surfaces and narrows it down to one real direction.

And that product is bigger than it sounds. It isn’t just your next move. It’s your future self — your fulfillment, your relationships, your influence, your options, the whole shape of your life. You spend more waking hours at work, with the people there, than you do anywhere else, so your career genuinely does shape what’s possible everywhere else in your life. But it’s not the other way around: your career matters because of what it does for your actual life, not the reverse. That’s usually the real reason behind a career choice in the first place — we just don’t connect those dots early enough, whether that’s in school, early in a career, or the moment we say yes to a new job.

Hypothesis testing. In plain terms: make a specific guess, test it small, see what actually happens, then adjust. Not “I’ll figure out my whole future” — one testable idea at a time. This is the same approach that works in a job search: try a specific angle, measure the response, keep what works, drop what doesn’t. Nobody gets it right by guessing once and hoping.

A prioritized backlog. In plain terms: you can’t work on everything at once, so you rank what actually matters and work top-down instead of sideways. This is what comes out of a real Strategy Session — not a pep talk, a ranked list of what to actually do next, in order, so you stop spinning on five things at once. My Stress Management Blueprint runs on the identical logic, just pointed at what’s stressing you out instead of what’s next on your to-do list: you rank the stressors, then work them one at a time instead of carrying all of them at once.

A strategic plan. In plain terms: a roadmap with real steps between where you are and where you’re going, not just a destination you think about sometimes. Turning a direction into an actual plan is what the Strategic Planning Guide is built for — because a goal without a plan is just a wish with a deadline attached to it.

Frequent checkpoints and working demos. In plain terms: you show your work regularly instead of disappearing until it’s “done.” I saw this play out firsthand leading a Toastmasters club. The group was full of busy people, and at some point they voted to cut meetings from weekly to every other week — more time between meetings should have meant more progress, right? It did the opposite. With less frequency and less focus, the club got worse, not better, and people achieved less even though they’d supposedly freed up an extra hour every other week. I moved us back to weekly. Both the club’s energy and people’s individual progress picked back up almost immediately. Frequency isn’t overhead. It’s what keeps the thing alive. I tell every coaching client the same thing: schedule the next call before you leave the last one.

Endurance. In plain terms: you build in real recovery, not just sprint after sprint until you break. This is core to what I call the Personal Endurance Formula, and it matters more than people expect — not just for your own sake. Practicing real self-care, real endurance, is where you build the empathy, self-awareness, and discipline you’ll need before you can actually lead or care for anyone else — a team, a family, the people counting on you. You can’t sustain that for long if you’re not doing it for yourself first. Clients build a real self-care and fitness routine that actually supports their goals as part of this work — health was a particular focus for Jim, right alongside everything else.

Continuous improvement. In plain terms: you review what worked, cut what didn’t, and keep adjusting instead of running the same playbook forever, no matter what it’s costing you. This is the one that actually explains Jim’s beach condo. Not raw effort — the habit of reviewing the plan and adjusting it, over and over, instead of just working harder at a plan that was never really working.

The Gap Isn’t Skill. It’s Application.

If any of this is landing, it’s worth sitting with why. It’s not that you don’t know how to do this work. You’ve probably done some version of it for an employer for years. The gap is that nobody ever pointed it back at you.

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