If you’ve ever felt like you’re doing all the things but not making any real progress, it might be time to rethink what “progress” even looks like and redefine milestones so you feel motivated … and so you stay that way.
See, when you’re building a business from your home office (or your kitchen table, or your parked car during a kid’s baseball practice — yep … been there, done that), traditional definitions of success don’t always apply.
You don’t get quarterly reviews or promotions. No one throws a party when you finally figure out a system that works. And unless you count yourself, there’s no boss to say, “Hey — that thing you just did? That was a big deal.”
And this means that you might be skipping over the milestones that matter most.
The Problem with Waiting for Big Wins
Most of us think of milestones as big, obvious moments — launching a new product, hitting a revenue goal, growing your audience to a certain number.
But when those big milestones are your only markers of progress, the space in between them can feel like a frustrating void.
You might actually be doing great things — showing up consistently, learning new skills, tweaking your offer, nurturing leads — but if you don’t see that work as progress, it’s easy to feel like you’re stuck or falling short.
And that’s when motivation starts to fade.
What If You Redefined What Counts?
Redefining milestones means expanding your definition of success to include all the moments that move you forward — even if they’re not flashy or final.
These are things like:
- Sending the follow-up email you’ve been procrastinating.
- Honoring your work hours by logging off when you said you would.
- Having a discovery call that didn’t convert — but gave you clarity.
- Saying “no” to a client that isn’t aligned.
- Taking a day off when you need to rest — and not feeling guilty.
These moments aren’t usually celebrated. But they should be.
Because they shape how you show up, how you make decisions, and how you build resilience for the long game.
Let that sink in …
The small moments should be celebrated, too, because they shape how you show up, how you make decisions, and how you build resilience for the long game.
Use Milestone Mapping to Track ALL the Wins
This month’s premium subscriber Mini Power Tool — the Milestone Mapping Method worksheet — is designed to help you break down your goals and chart out progress in doable, motivating steps. (Learn more about the Milestone Mapping Method here.)
But here’s the part most people miss: your map doesn’t have to be filled with only outcome-based milestones. You can (and should) include process milestones, too.
Think about the parts of your process that can be tracked, measured, and celebrated. Things like:
- “Send pitch email to 3 new podcast hosts” instead of “Get booked on a podcast”
- “Create content plan for next 2 weeks” instead of “Grow Instagram by 500 followers”
- “Set up a weekly admin block” instead of “Automate all business ops”
The worksheet helps you visualize those small but mighty wins, so you can stop feeling like you’re treading water and start recognizing your forward momentum.
Every time you check off one of those steps, you’re building confidence in yourself and trust in your systems. You’re proving that your process is working.
Why This Matters for Motivation
Motivation is largely driven by progress. But the way your brain registers progress isn’t just about finishing huge goals — it’s also about noticing small wins along the way.
When you acknowledge micro-milestones, your brain gets a little dopamine hit that says: “Hey, this is working.”
That positive reinforcement then creates a feedback loop.
The more wins you recognize, the more momentum you feel. And the more momentum you feel, the more likely you are to keep going.
That’s how confidence grows — not from the big wins, but from the dozens of small ones that remind you: I can do this.
Redefining Milestones Creates Real Motivation
Some of the most powerful milestones are the ones that no one else sees — the quiet, courageous, or consistent steps you take when no one’s watching.
That’s why your Milestone Mapping worksheet should reflect your real journey — not just the highlight reel.
When you fill it in this week, challenge yourself to:
- Include at least one process milestone that helps you work smarter, not harder
- Celebrate a mindset shift or boundary you set — even if it’s not finished yet
- Mark progress you made on something that previously felt “stuck”
You might be surprised how motivating it feels to see those steps written out — and celebrated as part of your success story.
Put This into Practice
Before you move on to your next big task, pause and answer this:
What’s a milestone you reached recently that wasn’t a final result?
Now open your Milestone Mapping worksheet and write it down.
Yes — it counts.
So do all the other behind-the-scenes, under-the-radar, build-your-own-way wins.
Because when you see your progress, you believe in your progress. And that’s what keeps you going — even when it’s hard.
💡 Want to Get the Milestone Mapping Method Worksheet?
If you’re a Tenacious WFH Insider or VIP, you already have access to the Milestone Mapping Method Worksheet in your private Tenacious WFH Entrepreneur Mini Power Tools Dropbox folder.
Not upgraded yet? You can explore your options here. Let’s make this summer one of sustained motivation and satisfying momentum — celebrating ALL the milestones along the way.