BREAKING BOTTLENECKS: How to Remove the Biggest Roadblocks to Growth

3 minutes ago
9 min read

You're not stuck because of the market, the economy, or bad timing. You're stuck because of you — and that's actually great news.

Let me ask you something.

If you disappeared from your business for thirty days — completely off the grid — what would happen?

No phone. No email. No “just one quick question.” Just gone.

Be honest.

For most entrepreneurs, the answer is uncomfortable. Things would slow down. Decisions would pile up. The team would either freeze or start guessing. And somewhere around day five, someone would find a way to reach you.

That's not a team problem. That's not a systems problem.

That's a bottleneck problem. And the bottleneck is you.

We know, because for years, we were the bottleneck in our own business.

John and I had built Hawaiian Vacations from nothing into a successful and profitable scheduled charter airline flying wide-body passenger jets between Alaska and Hawaii. From the outside, it looked like we had it figured out.

From the inside? We couldn’t leave.

Every decision cycled back to us. Every exception needed our approval. Every shift in strategy required our presence. We had built a thriving business that we were completely trapped inside.

This newsletter is about how we got out — and how you can, too.

Part 1: The Bottleneck Nobody Talks About

When entrepreneurs hear the word “bottleneck,” they think of a broken process. A slow step in the workflow. A communication gap. A software problem.

Those are real. But they’re rarely the deepest ones.

The deepest bottleneck in most small businesses is the owner.

And it happens gradually, invisibly, in the most well-intentioned way possible.

In the beginning, you do everything yourself because there’s no one else. You’re the salesperson, the bookkeeper, the customer service rep, the strategist, and the janitor. That’s just startup reality.

But here’s where it goes sideways: the business grows, the team expands, the systems get added — but your grip on the center of it never loosens. You shift from doing everything to approving everything. From executing to being consulted. From running tasks to being the last word on all of them.

The title changes. The dependency doesn’t.

And as long as you’re the person everything flows through, the business can only grow as fast as you can personally keep up.

So here’s the question worth sitting with: What in your business can only happen because of you?

The answer to that question is your map. Every item on that list is a bottleneck waiting to be broken.

Part 2: The Story of the Dull Axe

There’s a story we often tell our students, and it’s stuck with us for a good reason.

A man is out in the woods, chopping down a tree. He’s working incredibly hard — sweating, swinging, pouring everything into it. A passerby stops, watches for a moment, and notices the axe is completely dull. For all that effort, the tree is barely budging.

“Maybe you should stop and sharpen your axe,” the man says.

The woodchopper doesn’t even look up.

“I don’t have time. Can’t you see how busy I am?”

"I don’t have time to stop and sharpen my axe." That sentence is the unofficial motto of every entrepreneur who is stuck.

The problem isn’t effort. Entrepreneurs are some of the hardest-working people on the planet.

The problem is what all that effort is going toward.

Swinging harder on a dull axe just means more work for the same result. But stopping — even briefly — to sharpen? That’s what creates leverage. That’s what makes the next swing ten times more effective.

Building your systems and documenting your knowledge is sharpening the axe. Training your team to make decisions without you is sharpening the axe. Writing the procedure instead of just doing the task again yourself — that’s sharpening the axe.

It feels slow in the moment. It seems faster to do it yourself.

But you’ve been saying that for years. And the tree is still standing.

Part 3: What “Duplicate Yourself” Actually Means

We use this phrase in our course, and we want to be clear about what it does — and doesn’t — mean.

It doesn’t mean finding a clone. It doesn’t mean stepping away from leadership. It doesn’t mean the business runs itself while you sit on a beach somewhere.

It means this: the outcomes your personal involvement currently produces can be produced by your systems, your team, and your documentation — without requiring you to be there every time.

Here’s the story that made it real for us.

For years at Hawaiian Vacations, I was the one who would make the call on advertising spend. I would tell the marketing team when we needed to ramp up our advertising.

One day, one of them asked me a simple question:

“How do you know when to increase the budget? What are you actually looking at?”

I had to stop. I’d been making that decision for years — by instinct, by feel — and I had never once analyzed how or why I knew that was needed.

So I had to figure it out. What was I actually thinking about or looking at when I made that decision? What was the trigger?

Eventually, I landed on it. I had been noticing our sales trends. So I developed a formula: three consecutive days of declining daily sales volume = increase advertising.

That was it. That was the signal I’d been reading intuitively every time. Once I shared it with the team, the decision no longer needed me. They could make the decision themselves — correctly, consistently, without consulting me.

One insight. Out of our heads. Into the business.

That’s what duplication looks like. Not a grand overhaul. Just the steady, deliberate work of transferring what only lives in your head into something the business can use without you.

What decisions are you currently making that no one else in your business knows how to make?

That list is your starting point.

Part 4: Why Delegation Keeps Failing

Most entrepreneurs have tried to delegate. Many times, the results are disappointing.

The work came back wrong. The standard wasn’t met. The customer wasn’t happy. And somewhere in the back of your mind, a quiet conclusion formed:

“It’s easier to just do it myself.”

We understand that feeling completely. But here’s what we’ve learned after 45 years of building businesses:

When delegation fails, it’s seldom the person. It’s the handoff.

The task was vague. The standard was implied but never stated. The deadline was soft. The follow-up never happened.

And the person doing the work was left to guess at what “a good job” looked like.

Before we delegate anything now, we ask ourselves one question:

Could I describe what a great job looks like — specifically enough that there’s no ambiguity about whether it’s been done?

If we can’t answer that, we’re not ready to delegate. We need to get clear first.

Once we can answer it? The handoff has a fighting chance.

"Define what a good job looks like before you hand anything off. Vague expectations produce vague results — every time."

Trust But Verify — Always

People often comment that I'm unusually good at following up. Those things never seem to fall through the cracks with me.

Here’s the truth: it has nothing to do with memory or personality.

It has everything to do with a system.

I’ve used OmniFocus as my productivity management tool for over ten years. I call it my external brain. Every time I delegate something, I set a follow-up reminder — a specific date when I will check in. Not to hover. Not to micromanage. Just to confirm that the work is on track.

That one habit — applied consistently — is what prevents things from falling through the cracks. It’s not magic. It’s structure.

Do you have a system for following up on everything you delegate? If not, what’s one thing you could put in place this week?

Part 5: What You’re Actually Afraid Of

I want to communicate something that doesn’t always get said in business conversations.

The reason most entrepreneurs stay as the bottleneck isn’t a lack of knowledge. It isn’t a lack of time. It isn’t even a lack of the right people.

It’s fear.

Not the dramatic kind. The quiet kind. The kind that shows up dressed as logic.

“I can do this faster myself.”

“By the time I explain it, I could have just done it.”

“No one else will do it the way I do.”

Each of these statements can be true in the moment. In the short term. For one task.

But repeated hundreds of times across months and years, they add up to a business that is permanently capped by the very person who built it.

What helped us move through this wasn’t a mindset hack or a motivational quote. It was getting clear about what we actually wanted.

Did we want to keep being indispensable to the day-to-day? Or did we want a business that could give John and me the freedom to live the life we’d been working toward?

Those two things cannot coexist. You have to choose.

And when we got honest about that choice, about the vision for our life and for our future, letting go became easier. Not easy. But easier.

Part 6: Where to Start — Right Now

I want to give you something concrete to do this week. Not a twelve-step plan. Just one thing.

The One Question Exercise

Set aside twenty minutes. A quiet space, no phone. And write down the honest answer to this:

What am I doing right now that would stop — or slow to a crawl — if I wasn’t here?

List everything. No filter, no editing. Just get it on paper.

Then look at the list with fresh eyes. For each item, ask:

Does this genuinely require me — my specific authority, expertise, or relationships?
Or am I holding onto it out of habit, comfort, or a fear of letting go?
If someone else were properly trained and had a clear standard to work toward, could they do this?

The items in that last category are your bottlenecks. Circle the one that costs you the most time or causes the most friction.

That’s your starting point.

This week, choose that one thing. Define what “a great job” looks like. Either document the process, record a video of yourself doing it, or write down the decision criteria you use. Then hand it off — with the clarity and the follow-up reminder in place.

One thing. Done properly. That’s how this starts.

And one thing, done well, will teach you more than ten things done halfway.

Part 7: What’s Waiting on the Other Side

I want to describe what it actually felt like when we broke the bottleneck at Hawaiian Vacations — because I think it’s worth knowing what you’re working toward.

It happened slowly. One system at a time. One decision criteria written down. One team member is trained to handle something that used to require us. One follow-up reminder was set and honored.

And then one day, John and I took a real vacation. Not the kind where you spend half the trip on the phone. A real one — completely disconnected.

The business didn’t fall apart. It ran.

That was when we knew we were onto something.

We started being able to think about the business from a different altitude. Not from inside the daily operations, but above them. We had space to ask the questions that actually move a business forward:

Where should we go next? What do we want to build? What does the next chapter look like?

That’s the owner role. That’s what it actually feels like when the bottleneck is broken.

Not a business that requires less of you. A business that requires the right things of you.

And that distinction — operator versus owner — is everything.

"A capable captain makes constant course corrections. But they can only do that if the crew knows how to run the ship."

You built this business. Now build the version of it that doesn’t need you to run yourself into the ground to keep it going.

One bottleneck at a time.

One brave, uncomfortable, ultimately liberating act of letting go.

That’s how you start Livin’ the Dream.

Expert Spotlight

Phil Lashley

Independent Visual Storytelling Strategist & Framework Designer

Phil Lashley works with leaders, consultants, and teams to turn complex ideas into clear visual stories and frameworks that people understand, remember, and act on.

His work sits at the intersection of content strategy and presentation design, helping visionaries shape both the narrative and the visual structure of their ideas so they can be taught, sold, and scaled.

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