I’m The Real Jason Duncan, back with another Beyond the Grind blog — helping entrepreneurs like you build thriving businesses without sacrificing your freedom. 🚀

Let’s talk about something most founders never name but always feel.

I’ve built and exited companies.
I’ve had years where everything clicked – and years where I wanted to walk away.
And sometimes?
I’ve felt like five different founders in the same year.

One month I’m flying high.
The next I’m burned out.
Then I’m dreaming again.
Then I’m stuck.

It used to feel inconsistent. Like something was wrong with me.

Now I know better.

It’s not inconsistency — it’s seasonality.

Entrepreneurs move through internal seasons just like nature does — but unlike the weather, these seasons don’t follow a predictable pattern.

You won’t go from Flow to Drift to Grind in order.
Some seasons last weeks. Some last years.
You might repeat a few. You might skip one altogether.

That’s why naming the season you’re in matters so much.

If you don’t know what season you’re in, you’ll misdiagnose the problem — and apply the wrong solution.

You don’t need to sell your business or blow it all up to escape the chaos.

You just need to recognize the season you’re in — and learn how to lead yourself through it.

Over the past decade and a half, both as an entrepreneur and as a business coach to some of the most successful founders in America, I’ve discovered seven distinct seasons of entrepreneurship.

These aren’t business lifecycle stages — they’re emotional and mental cycles every founder moves through.

Let’s dive in.

The 7 Seasons of Entrepreneurship

This isn’t a business lifecycle. It’s an emotional and mental one.

These are the internal states entrepreneurs cycle through.

They’re not linear — and they don’t always show up in order.

But once you learn to name them, you’ll stop reacting — and start leading.

Let’s find your season.

The Flow

Momentum is high. But so is your blind spot.

Everything’s working. You’re in rhythm. Energy is up. Wins are stacking.

But you’ve stopped checking the basics. You’re moving fast — and overlooking the cracks.

You might be in The Flow if…

• You’re hitting big wins but haven’t looked at your SOPs in 6 months
• You’re making fast decisions and skipping reflection
• You think, “Things are good – what’s next?” but haven’t answered it yet

The Drift

You look successful – but you feel scattered.

You’re hitting your numbers. Nothing’s technically wrong.

But you’re disconnected. The spark’s gone. You’re running the machine, but you’ve stopped dreaming.

You might be in The Drift if…

• Your calendar is full, but your mind is foggy
• You’re checking boxes without excitement
• You keep saying “I’ll figure it out soon” but never do

The Grind

Everything feels heavy. You’re stuck in reactivity.

You’re not burned out yet — but you’re getting close.

The business is running you. Every task feels like a chore. You’re tired, resentful, and overcommitted.

You might be in The Grind if…

• You start most days with, “Not again.”
• You’re snapping at your team — or your family
• You can’t remember the last time you felt excited about the business

The Storm

This isn’t just stress. This is crisis.

Something broke.

A deal fell through. A partner bailed. Health, finances, or systems took a hit.

Now it’s personal — and you’re questioning everything.

You might be in The Storm if…

• You’re anxious more than frustrated
• You’ve lost confidence in your instincts
• You’ve said, “I don’t know if I want this anymore” out loud

The Realignment

Your compass is recalibrating.

The fog is lifting. You’re asking better questions.

You’re re-evaluating — not just your goals, but your values.

This is the season of reflection, not rapid action.

You might be in The Realignment if…

• You’re journaling or praying more than usual
• You’ve stopped chasing what used to motivate you
• You’re finally saying “no” to good things to make room for better things

The Margin

You’ve created space. Now steward it.

You’ve cut back. You’re breathing again.

This is the rhythm phase — restoring energy, vision, and rhythm before the next big season begins.

You might be in The Margin if…

• You’ve reduced your hours — and your stress
• You’re enjoying time off without guilt
• You’re thinking proactively again

The Threshold

You’re not stuck – you’re evolving.

Something new is forming.

You’re outgrowing the old version of yourself, but the next version hasn’t fully arrived.

This season is filled with tension, vision, and identity shifts.

You might be in The Threshold if…

• You feel both excited and restless
• You’ve been saying, “I think I’m about to…” a lot lately
• You’re thinking more about legacy than lifestyle

Now What?

If you saw yourself in one — or three — of those, good.

This isn’t about boxing yourself in.
It’s about giving language to what you’re feeling so you can lead yourself clearly.

When you can name the season, you can respond the right way.

Because if you misread the moment…

You’ll push when you need to pause.
Or pause when you need to pivot.

But when you name it right — you lead it right.

Each season needs a different mindset and a different strategy.
And if you apply the wrong one? You could actually make things worse.

Words of Wisdom

“To everything there is a season, a time for every purpose under heaven.” – Ecclesiastes 3:1

Until next time…

Go beyond the grind,
The Real Jason Duncan 🚀