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Strategic quitting: when to stop flogging a dead horse
This article is for the self-starters: business owners, side hustlers, and entrepreneurs, or those hoping to be one day. It's about knowing when to quit.
Let me start with a confession.
Many years ago, I read a book so depressing I nearly gave up coaching.
It was late 2016. 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. Despite the glam Instagram stories of coconuts and surfing lessons, living on an exotic island with little or no income had more downsides than good vibes.
Enter 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. Its duration is uncertain, and so is its destination, with three scenarios possible: a steep ascent towards success, a sheer cliff into personal ruin, or a dull cul-de-sac into mediocrity.
What does the dip look like?
You'll know you've hit the dip when, after a period of initial excitement, steep learning, and low-hanging 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 for selling your wares, and you're at a loss when it comes to finding the next customers. You feel like nothing is working any more and maybe even fear going bankrupt.
The 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.
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 the people 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. You also operate in a world where ChatGPT makes it possible for anyone with a laptop and a brain to write pretty decent blog posts and articles.
These AI tools have become the equivalent of having a really good intern at your side 24/7. So you'll have to perform much better than that AI intern for your freelancing business to survive.
To make your business thrive, you must commit to mastering a whole set of additional skills. Once you've hit the 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
Being the best is highly subjective. 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, and then committing 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. No need 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. 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.
Being the best at something doesn't exclude you from being a generalist in other areas or having broader skills too.
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. 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 get to split the cake.
The easier it is to enter a market, the longer and harder the dip, and the more complex the journey to mastery.
Life coaching is a good example. 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 who have the patience and 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. Take some time to zoom out and honestly assess whether your venture has any reasonable chance of success. Is the market saturated? Is your industry declining and has no future? Have you run out of finances, or are you likely to soon?
If yes, ask yourself: is it worth pivoting into a different market?
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.
It's also 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 of 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, instead of 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.
If you're merely going through the dip, push through. 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.
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 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.
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 fact: there would be no shortcuts to coaching success and mastery.
The fact that you're reading this article means I made it past my own dip eventually. 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. Perhaps if I'd been more realistic, I might 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. Let's say it's a blessing that OnlyFans didn't become a thing until 2020.
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, my voice isn't world-class. Each venture made me just enough money to allow me to continue mastering my coaching skills.
If you're currently running your own business, in the process of setting one up, or seriously thinking about doing so, let me leave you with a few questions worth answering for yourself:
- Am I facing a dip, a cliff, or a cul-de-sac?
- Am I panicking?
- What am I doing that doesn't work?
- What progress have I made so far? Am I moving forward, regressing, or standing still?
- If it's a cul-de-sac, how can I change it into a dip?
- If I quit now, am I doing it for short-term gain and ignoring the longer-term potential?
- Is my persistence likely to pay off in the long run, or am I so invested already that it's too late to pull out?
- When should I quit? I need to decide now, not when I'm in the middle of a dip or part of me is begging to quit.
- If I quit a particular task, will it increase my ability to get through the dip?
- If I'm going to quit anyway, is there something dramatic I can do instead that might change the game?
Want to think this through with someone? Book a free consultation call.