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Strategic Quitting: When To Stop Flogging A Dead Horse


Quit the wrong stuff

Stick with the right stuff.

Have the guts to do one or the other.

– Seth Godin

This article is directed at all of the self-starters among you. The business owners, side hustlers and entrepreneurs – or those hoping to be one someday.

It’s about knowing when to quit.

But let’s start with a confession.

Many years ago, I read a book so utterly depressing that I nearly gave up coaching.

It was late 2016, and I’d recently moved to Asia on a midlife-whim after a major career pivot from being a lobbyist into life coaching.

In contrast to the back-of-the-envelope business plan I’d put together a few months earlier, business wasn’t picking up nearly as fast as I’d predicted. And despite the glam Instagram stories of coconuts and surfing lessons, living on an exotic island with little or no income turned out to have more downsides than good vibes.

Enters The Dip by marketing guru Seth Godin. It’s a short read – a rare blessing for personal development books – and although poorly written, it packed a punch that nearly sent me back home.

In it, Godin talked about strategic quitting and accepting that not every challenge is worth fighting for.

The ‘dip’ refers to the struggle and frustration any venture goes through once the honeymoon period has ended.

Aside from its duration, the dip’s destination is uncertain too, with three scenarios possible – a steep ascent towards success, a sheer cliff into personal ruin, or a dull cul-de-sac into mediocracy.

What does ‘the dip’ look like?

You’ll know you’ve hit that dip when after a period of initial excitement, steep learning and low-hanging initial success, your venture feels like it’s slowing down. Having taken your foot off the pedal somewhat, you’ve stopped learning as much, and things don’t feel as fun as they once did.

Maybe you’ve run out of friends and family to tap into for selling your wares, and you’re at a loss when finding those next customers. You feel like nothing is working anymore and maybe even fear going bankrupt.

This dip is a prolonged period of suffering where your resolve gets tested to see if it’s worthy of the spoils.

The winner takes it all

According to Godin, pushing through the dip is often not worth it, and you're better off calling it quits. The only circumstance in which you should persist is if you feel there's a reasonable chance that you can see yourself becoming the best in the world.

Indeed, markets don't reward average, he says, so the only way to thrive is by blowing your competition out of the water and becoming the best at what you do.

Those market forces reward those on top way better than those who rate second. Being the best is a rarity; everybody wants to work with a winner, and that winner takes it all.

Say you've decided to start freelancing as a content writer because you have a nose for storytelling and coming up with great ideas. But you also operate in a world where ChatGPT makes it possible for anyone with a laptop and a brain to write some pretty decent blog posts and articles.

These AI tools have become the equivalent of having a really, really good intern at your side 24/7. So, you'll have to perform way better than that AI intern for your freelancing business to survive.

However, if you want your business to thrive, you must commit to mastering a whole set of additional skills. That's because once you've hit that dip, you'll be competing with AI tools and tens of thousands of other freelancers trying to do the same thing.

Being the best in the world

Of course, being the best is highly subjective, and I'm not encouraging you to compare yourself with others needlessly.

It's less about competitive metrics than believing you can master a particular activity or skill. You then need to commit to that mastery fully.

You shouldn't take the 'world' too literally, either. I'm talking about your world, so define it however you want.

It could be the world of wedding photography, digital marketing, cupcakes, screen printing, cold calling, yoga retreats, accounts payable, financial services recruitment, or – god forbid – life coaching.

You can also be the best in whichever geographical area you operate, rather than needing to set the global standard. You may decide to be the best craft beer brewery, corporate lawyer, diversity trainer or party planner in your local area, so no need to Elon Musk it and reach for the stars. The global market is divided into millions of little and not-so-little submarkets, and you get to pick which one to focus on.

The best also means something other than the most expensive. You can have the best service or product in a low-budget segment and still do better than if you were average in a top-tier market.

Besides, being the best at something doesn't exclude you from being a generalist in other areas or having broader skills too – something I'll discuss in next month's newsletter.

To get past your dip, be clear on your market and commit to being the best in it.

What can you expect after the dip?

Godin predicts three possible scenarios.

1) A steep ascent

As a rule of thumb: the longer the dip, the greater the spoils at the end of it. That’s because most of your competitors won’t bother and will give up. By the end of the dip, only you, and perhaps a handful of others, will have braved the waters and therefore get to split the cake.

The easier it is to enter a market, the longer and harder dip and the more complex the journey to mastery.

Life coaching is an excellent example of this. There are virtually no barriers to entry, which is why there are way more novice coaches than clients. Only those whose services are worthy, and have the patience and the resources to get themselves past the dip, might make it.

2) The cul-de-sac

You know you’re in a cul-de-sac when you realise there’s no pot of gold at the end of the dip.

Your levels of achievement, results, and even your skills have flatlined with no significant upward movement on the horizon. Your frustrations have led to complacency, and your motivation to be the best has evaporated with little chance of recovery.

That’s a hard place to be, but you still have a chance to get out of it. Take some time to zoom out and honestly assess whether your venture has any reasonable chance of success. Is it that the market is saturated? Is your industry declining and has no future? Have you run out of finances, or are you likely to very soon?

If yes, ask yourself: is it worth pivoting into a different market/world?

Can you be bothered?

3) The cliff

Occasionally, and despite doing everything correctly, the dip is just too big to overcome. The world may be too large, and your best may never be good enough.

Or it’s possible that whatever venture you’ve chosen carries a significant risk of financial ruin and damage to yourself, others, or the environment. Maybe you’re liable for legal or ethical violations. All these make your business a complete non-starter, and you should step away now.

Quitting is the only viable option to protect yourself and others from severe consequences.

Knowing when to quit

Seth Godin defines strategic quitting as quitting the right things at the right time rather than gritting your teeth and draining your resources without adequate returns. If you find yourself facing a cliff or a cul-de-sac scenario, you must quit as soon as possible.

However, if you're merely going through the dip, you must push through. As we saw earlier, the longer and deeper the dip, the better because fewer competitors will be left once you make it out. As Godin puts it, this dip is why you succeed and if there wasn't one, literally anyone could replace you.

I'll also point out that, putting macroeconomic factors aside, you are primarily the deciding factor as to which of these scenarios you end up in.

Can you handle the tedious and challenging work typical of a long dip? Do you double down on becoming remarkable at what you do, or do you start cutting corners and delivering mediocre work? Can you handle the dark side of freelancing and running your own business?

Only those who deliver exceptional work and become the best in their world make it out to the other end.

To finish on a personal note

The reason I found The Dip such a depressing read back in 2016 was that it forced me to acknowledge a hard truth: that there would be no shortcuts to coaching success and mastery.

The fact that you're reading this article means that I clearly did make it past my own dip eventually. But it took me a good four years to build a consistent enough client base to make it a viable business. My back-of-a-fag-packet business plan had prioritised hope over realism. Although, perhaps if I'd been more realistic, I may never have started.

To make ends meet, I had to set up various other ventures, including content writing, translation, training language AI systems, property reviewing and voice-over acting. I'd try any odd job I could do remotely to bring some money in, so let's say it's a blessing that OnlyFans didn't become a thing until 2020.

And despite some initial successes with each of those ventures, none made it past the dip. For the most part, I wasn't motivated enough to become the best at it, and in the case of the latter, because my voice isn't world-class. Yet, each venture made me just enough money to allow me to continue mastering my coaching skills.

So, if you're currently running your own business, are in the process of setting one up, or are seriously thinking about doing so, let me leave you with a few questions worth answering for yourself.

1) Am I facing a dip, cliff, or cul-de-sac?

2) Am I panicking?

3) What am I doing that doesn't work?

4) What progress have I made so far? Am I moving forward, regressing, or standing still?

5) How can I change it into a Dip if it's a Cul-de-Sac?

6) If I quit now, am I simply doing it for short-term gain and ignoring the longer-term potential?

7) Is my persistence likely to pay off in the long run, or do I feel I'm so invested already that it's too late to pull out?

8) When should I quit? I need to decide now and not when I'm in the middle of a Dip or when part of me is begging to quit.

9) If I quit a particular task, will it increase my ability to get through the dip?

10) If I'm going to quit anyway, is there something dramatic I can do instead that might change the game?

So to all of the self-starters out there, I salute you. Here's to some extra luck and courage either way.

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Before you bow out

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I send out one short email at the end of each month with a few practical tips on how to develop a more meaningful and exciting life and career.

You'll also be the first to find out about my next group coaching programme and upcoming retreats.