Why you can’t enjoy your holidays

A few summers ago, I was on a driving holiday in Scotland.

Glorious.

Driving through the dramatic landscapes of Skye and Inverness… I felt like I was on Route 66 or something.

(Not that I’ve never been on Route 66. It just felt a little otherworldly.)

Apparently, it rains a lot in Scotland.

Not this time — we had 2-3 weeks of pure sunshine.

Said everyone:

“This never happens. You don’t know how lucky you are!”

We ended up in St Andrews.

The beach, the golf course, the town… all basked in summer sun.

I felt incredibly lucky.

Unfortunately, I didn’t feel good.

See, a few days into the holiday, someone on my team forwarded me a cashflow report from my business StoryLearning.

“Something’s not right,” they said.

Money wasn’t coming in and we didn’t know why.

Now, if there’s one thing you don’t want to hear right at the start of a big holiday, where the whole purpose is to relax, destress and chill, it’s the words “something’s not right.”

FFS.

Now, I couldn’t do anything about it myself. I didn’t even have my laptop with me.

So I relied on my team:

“Please dig into it and keep me updated.”

Over the next week or so, we were back-and-forth on WhatsApp.

Trying to diagnose the problem.

Failing.

The longer it went on, the more anxious I became.

There’s only one thing worse than having a major problem in your business:

Having a major problem… and not being around to fix it.

I won’t bore you with the details.

But long story short:

Despite the incredible surroundings and weather, uninterrupted family time, and so in…

I spent much of the holiday anxious AF.

I remember my daughter saying:

Why is Daddy always on his phone?

That bit hurt even more than the business anxiety.

(Parents will get it.)

And you want to know the hilarious bit?

Go on then, I’ll tell you…

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It ended up being a reporting error 🙂

A total nothing burger.

Holiday ruined. For absolutely nothing.

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Now look —

You’ve got to go through these kind of experiences in order to learn from them.

And there’s not a seasoned entrepreneur reading this who hasn’t had this happen to them at least once.

What matters is that you learn from it.

Put in place structures to safeguard your own headspace, so that you can’t be easily railroaded like I was on this holiday.

Getting this right doesn’t just affect your wellbeing.

It makes you a much more effective entrepreneur and CEO too.

“But how do you prevent this?” I hear you cry.

I’m glad you asked.

So here’s what prompted this story…

An entrepreneur I’m working with in the UK told me the other day:

Last week I officially stepped down as CEO of the company.

It was our final mentorship call

I was proud of him.

See, when we started working together just over a year ago, his stated goal was to be “out of the day-to-day” in 6 months.

I gotta admit, I was doubtful.

Not many people achieve this.

But all credit to him — he pulled it off.

(OK, it took 12 months rather than 6… but he did have the great Google apocalypse to navigate. I’m publishing a case study on this in April – stay tuned.)

Anyway…

In our final call, he talked about the semi-retirement he was looking forward to enjoying. The peace of mind he craved.

I asked how he was going to engineer and protect this peace of mind:

“I get a weekly cashflow report.”

Alarm bells immediately started ringing in my head.

See, I don’t see how it’s possible to be receiving a weekly cashflow report, and also be chill.

Now… I get the impulse.

After all, cashflow reports are the lifeblood of the company.

However, weekly finances can lie to you.

Blips happen.

It’s possible to have a week where you make 50% of the revenue you normally make.

And then the following week it’s 150%.

Making the grand total of — you guessed it — 100%.

All good, right?

Except, if you receive the first week’s report last thing on a Friday afternoon, guess what’s happening?

You’re spending the whole weekend wondering if the business is falling apart.

Weekend lost.

That’s what.

(This is what happened to me in Scotland.)

And we want to avoid that.

To live a chilled live as business owner (not CEO), a few things have to happen with finances:

  1. You need to see key financial reports monthly or quarterly — NOT weekly
  2. Someone other than you needs to own KPIs around finances
  3. You need safeguards, so that if there’s a problem the KPI owner can’t handle, it automatically gets escalated to you

There are all kinds of benefits to seeing reports at less regular intervals.

For one, you avoid those reporting blips that can send you sideways unnecessarily, ruining your negroni and disturbing your sunsets.

More important: It’s easier to spot trends when you’re looking at the macro scale.

Don’t underestimate this —

Trends reveal themselves over months and years, not days and weeks.

Where you’re very close to the numbers, it’s much harder to notice larger trends.

From a strategic perspective (which is your job), nothing much matters on a weekly timescale.

The only thing you need to be sure of is that the alarm will be sounded if there’s a problem, and that’s where the safeguarding comes in.

I call it an Early Warning System.

And the best EWS is stupid simple.

You simply define the core KPIs for the business — whatever that is for you:

  • cash in
  • leads
  • traffic
  • CPL/CPA

And make sure a senior person is monitoring those weekly.

  • If any one metric is down >20%, monitor it.
  • If it’s still down the following week, escalate it.
  • If any one metric is down >50%, immediately escalate it.

Doesn’t need to be any more complicated than that.

In fact, it shouldn’t be.

But this is enough for you to sleep at night, while also allowing you to add value by keeping distance.

(Counterintuitive, but there’s a lot to that last sentence.)

So my advice to my entrepreneur friend was to get some altitude between himself and the reports.

  • Cashflow reports once a quarter (it’s not a cash intensive business)
  • KPIs once a month
  • A clear system for escalation

To be clear: The team will be looking at this stuff weekly.

Just not him.

Team building is supposed to buy you your freedom and headspace — so use them to help you achieve this!

And if you have good people, trust them to manage things properly.

It’s funny…

In many ways, business continues to be hard.

Just in different ways.

Anyway, hope this gives you some perspective.

Namaste,

Olly

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