An urgent letter to myself about the importance of making decisions as a small business owner.

Why is it so easy to get stuck on tomorrow’s pains when running a small business?

I think it’s because tomorrow’s pains are sexy and rounded, and they play to the vanities of what we imagine our best selves — our best businesses — to be. Whereas today’s pains are difficult and ugly, and they highlight the very insecurities that keep us from ever realising that better version of ourselves and our businesses.

I think it’s safe to say that I’m not alone as a business founder in knowing where I want to get to with the business. The image is incredibly clear in my head. And that’s great.

It’s also easy. Which is precisely why it’s such a pull on mental resources.

In truth, that vision should only ever be a motivating factor — an outline — to guide the decisions we make in our businesses every day. As soon as we start painting the colours or shading the details of that outline, we’re doing nothing more than dreaming. We procrastinate with good intent.

Because if I have a vision of where I want to move my business to, then by definition that vision is not where I am right now. And any fool can imagine success. The world is full of the people who could have built Facebook if only they’d had the time, the advantages, the luck, the [insert endless other excusatory noun here]…

You know the deal!

So let me offer an insight into the very situation that brought this learning home to me in the past 24 hours.

Yesterday I was working on the new website for Principal Publishing — the business I founded with my wife almost fifteen years ago. The company is in transition from what it was — effectively three complementary but separate businesses — to what we want it to be — a single business with a defined audience and a unified approach. Via a number of intermediary stages along the way.

This new website is live, and incredibly basic. So basic, in fact, that it offends my designer’s eye.

But while working with my business mentor, he pointed out that I’ve spent so long iterating on this new website and brand in private, that if I don’t make it public at some point then it’ll never happen. We’ll be stuck in a purgatory of “not quite good enough”. Because it never can be good enough.

So — with his (strong) encouragement — I made the new site live. You can see it here.

I know, it’s not great. I get it. It’s a single page. The styling is unfinished. The layout is all wrong. The content is not ready. The narrative flow of the brand is not there yet. The new client portal isn’t ready. And it hurts that I know there are lots of much better versions in draft form but that also aren’t ready in other ways.

But it’s there.

And the fact that it is finally public is a much stronger motivating factor than a thousand almost ready versions in private. Evidence for this is the progress we’ve made on associated aspects of the business transition since we made that site public less than two weeks ago. Simply because being public has an unforgiving quality that shines a harsh light upon the obvious next most important task.

So, the lesson worked. Right?

Well…I’m glad you’re paying attention. But here’s the thing…

A big characteristic holding back most small or tiny business owners from actual entrepreneurship (as distinct from simply operating a business) is hesitancy.

Some call it procrastination. Or fear. Or perfectionism.

You call it what you will — and I believe there’s a strong argument that those things are one-and-the-same — it’s essentially a characteristic that prevents us from moving forwards with our businesses.

I heard an anecdote from Scott Galloway on the DOAC podcast while showering this morning. Though we can debate the truth of it, the sentiment struck home, and I think it’s a worthwhile detour that helps illustrate the point I’m trying to make.

Scott was asked about his experience of business and entrepreneurship as an American living in the UK. He summed it up with a generalism: that someone in the UK with a successful restaurant will love that successful restaurant as an end in itself. Whereas a similar someone in the US will see their successful restaurant as an opportunity; a means to open another restaurant, and then another, and then an entire chain of them.

Which is an interesting a point of view in itself. But the real insight came next.

He believes that this is actually something baked into the mindset of our two nations. How? Well the argument goes that America is a nation of immigrants. Many Brits — and many others too, of course — fled their home shores at some point long gone in search of something new. Something better. With a huge element of risk inherent in that move, they took a chance. That’s the psyche of the United States. Back here in the UK…we’re not the risk takers. We’re the ones who stayed.

This is not a letter about the merits of nations or the primacy of peoples. That’s not where the value lay for me in this discussion.

The actual value — and whenever we hear a lesson or an insight from someone we respect, this should always try to apply it — comes when we turn that insight back on ourselves and reflect upon it.

And for me those thoughts laid bare how my own fears hold me back from the risks — small or large, real or imagined — that could move my business forward in the way it deserves.

Because hesitancy and procrastination and fear and perfectionism comes in many forms. But the most devilish of those is activity.

Which brings me full circle back to where I began this letter.

Because even when I was working on those tasks related to the new website — in itself an operation in focusing on what matters in my business — I was sucked into a job which was not at all important now.

Before I knew where I was, I was three hours down the rabbit hole of figuring out how something might work if we get lots of other things right in the meantime. I was shading in the detail of an outline that will change shape many times long before I ever get close enough to really understand what it is.

And it’s this kind of activity based in fear, presenting as procrastination, and dressed up as perfectionism, that prevents so many of us from taking the leaps we otherwise might.

I was wasting my time on fantasy pains that I want to face in the future. Because that’s far easier than getting my head down and working on the actual (painful) pains that I am facing in the business right now. Those pains are hard. They require focus. And whether or not I’m successful in dealing with them will be blatantly obvious to me fast! Because those real pains I should be spending my time addressing will have immediate pay-offs or problems according to what I do today.

Whereas those fantasy pains? Just fantasy!

It’s entrepreneur porn — playing at business rather than rolling up the sleeves and getting down to it.

So here’s where the message really came home to me.

As small business owners, one of the few advantages we actually have over the big guys is the ability to move fast. To have an idea and act on it. To make decisions free of bureaucracy. That is something we can all do as small business owners, because there’s nobody to stop us but ourselves.

We’ll often have no money. Usually few resources. Sometimes little experience to call upon. But we can make decisions fast.

So if I don’t do that — if we as small business owners don’t do that — then I’m voluntarily giving away what Nicolas Cole calls my unfair advantage; i.e. the very thing I should be majoring on right now to help me make those leaps forward in my business.

In effect we create businesses with no money, few resources, little experience to call upon, yet still a huge bureaucracy — only it’s a bureaucracy of the brain. A bureaucracy of our imagination. And that will become a huge tax on the mental resources needed to do what is actually required to move the business forward in the way it deserves; the way our customers deserve; and the way we deserve.

James Clear — of Atomic Habits fame — talks about all decisions falling to three categories:

• Hats — these decisions are easily swapped out and changed for another.
• ⁠Haircuts — get these wrong and you’re going to notice, but that hair grows back and you get another shot at it.
• ⁠Tattoos — these are potentially painful, definitely hard to undo, require deeper thought, but the decision still needs to be taken.

There’s a danger that we treat every business-related decision like it’s a tattoo. When in reality they’re probably haircuts at worst. And actually, for small business owners, our decisions are mostly just hats.

By dwelling in the future — by worrying about the impact of our decisions on a land we’ve imagined but not yet created — we’re holding ourselves back from ever getting to that land at all.

• Every decision becomes a tattoo when we imbue it with such significance
• By focusing on the future, even with the best of intentions, we take our eye of what can really have an impact now.
• This very hesitancy holds us back from being able to truly experience and enjoy the opportunities that this small business advantage should empower us with…the very magic of the possibilities we saw when we pictured escaping the nine-to-five, or as kids when we imagined the freedom of business.

So remember this: future pains will take every second you give to them and still not be satisfied, because there are so many potential pains down the line that you cannot possibly scale your mind to resolve them. You’re not meant to resolve them. But that false feeling of resolution to a fantasy pain of the future is like dopamine. You can move onto the next one and get another hit, without ever making any impact at all.

Whereas the real pains in your business today remain unattended to. They’re hard work. But the hard work is where the gold is.

So the next time you’re showering or walking or sipping a good coffee and that insurmountable problem jumps into your mind for the 87th time…stay with it. Don’t let your head jump to one fantasy pain after another. Notice what’s going on, and bring it back to that one insurmountable thing stopping you moving forward. Stay with it. Think on it.

You will likely have a very small number of actual priority pains in your business right now. Yes you can list twenty or thirty. But you know which two or three of those are the real zingers.

Move into those pains and ask what the decision is that you need to make. Then ask yourself how big of a decision it really is.

If it’s a hat decision, make it fast. Make it now. Try it out. Commit to an approach — any approach is better than none if you’re even slightly competent (and you are). See how it goes.

If it’s a haircut decision, take a little time to consider all of the information you already have, and go with the one that has the evidence in its favour. Commit. If it’s an awful haircut then yeah, people will notice. People might laugh. But in a short while you get to go again with the advantage of a valuable lesson learned.

If it’s a tattoo, you’re going to want to gather more inputs. Consider each option. Let it have space in your brain. You’re going to want to live with that decision for a while and actually do the hard yards in wrestling with it, getting to know it, and understanding it. But Remember why you’re making the decision in the first place. Give yourself a deadline. A decision will have to be made, and you’ll need to recognise the point at which you have all of the information you’re ever going to get. That’s the point at which you risk slipping again into the arms of those four horsemen of business apocalypse: Hesitancy. Fear. Procrastination. And perfectionism.

But for goodness sake, make the decision.

You and your business have a vitality that should be tested, and a power that can change your life for the better. A power to make you happier.

And why else are we in business at all, if not to be happy?

So. Don’t be the one who stayed.

Remember this, because you’re going to need to learn this lesson again.

And then learn it again.

And again.

You’ve got this!

Andrew. 🫶