The art of applying stoicism to sales craft

In 2022, it felt like the four horsemen were running riot. Wars and pandemics were sending economies haywire. I was also approaching 40 and these things combined led to a textbook mid life crisis. My cliche of choice was getting into Stoic philosophy.

Stoicism has been co-opted by macho bros, but it’s really about reason and self-control. Stoics believe the key to a happy life (Eudaimonia) is living by Hellenic virtues; Wisdom, Temperance, Justice, and Courage.

It’s ~2000 years old, often mistranslated, and based on writings from the Late Stoics (Epictetus, Seneca, and Marcus Aurelius lived centuries after it was created). But, in spite of its age and lack of primary sources, I find it to be an optimistic, empowering guide to modern life. At the risk of sounding like one of those people saying “here’s what x taught me about sales”, here’s what Stoicism taught me about sales.

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The dichotomy of control: “If it is not up to me, then I am not concerned” (Epictetus)

This is one of the most well known concepts. Stoics talk about having the wisdom to recognise the difference between things we can control, and things we can’t. A common example is not being able to control how other people feel or perceive us, we can only control our judgments, intentions and responses.

Controlling the controllables is a great mindset for sales. The simplicity of sales is how ruthlessly results driven it is. But those results are rarely fully in our control. We’ve all got examples of doing things right, but not getting the win, because the budget was pulled, or the CFO chose a cheaper option, or we didn’t realise the incumbent had it sewn up (not perfect examples, you could argue all of these things should have been qualified).

Valuing the process over the outcome gives the required level of swagger that good salespeople need. It stops us getting paralysed trying to second guess every decision. It allows us to get back on the horse when we don’t get the win we think we deserve.

Reasoned choice: “The greatest remedy for anger is delay” (Seneca)

Having the wisdom to recognise the things that are up to us, and the things that are not is only the start. Often we know these things, but our emotions influence us. Reasoned choice (Prohairesis) is about controlling ourselves. Stoics argue that is really the only thing we can control. There is a misconception that Stoics try not to feel things. But that is far from the truth. It’s about recognising your emotions, understanding how they influence your thoughts and actions, and then accounting for that.

Don’t believe the bravado. Sales is pretty emotional. Pitching is about inspiring and persuading. Closing can be about maintaining excitement and handling uncertainty. Negotiation often involves pride and fear. In this climate, it’s easy for salespeople to lose focus and discipline. Stoicism calls for temperance (self-control). Recognise how you feel, then decide how to respond. This is very powerful when having hard conversations. It’s easier said than done when you like the sound of your own voice.

Loving your fate: “Whatever happens, happens justly” (Marcus Aurelius)

We’re getting into the heavy stuff now. Loving your fate (Amor Fati) is about accepting all events, whatever they are. Epictetus says freedom comes from mastering your desires, not fulfilling them. Stoics build this strength by rehearsing hard times in their minds (Premeditato Malorem). A well known example of this is the medieval practice of Memento Mori. Physical reminders that we’re all going to die. Not something most sales leaders consider during their weekly pipeline reviews. But, in Stoicism it’s the ultimate motivator. There’s a story I’ll get wrong about a man telling Epictetus they were scared of dying, and he responded, when did you start living?

In sales, preparing for adversity is common. Good qualification should involve thinking about what could go wrong, and whether you’re able to mitigate that. The focus is to be better prepared with materials and arguments, but the Stoics would say you’re also better prepared to be resilient when the inevitable problems arrive.

Sales also involves doing things we should, but don’t want to. I’m sure we’ve all written outbounds then hesitated to send. Or delayed a hard call with a client. Stoics would say if these are the right thing to do (because they’re just and wise) then we need to do them now. And if that isn’t enough motivation, remember you’ll be dead soon anyway!

“Man cannot learn that which he thinks he already knows” (Epictetus)

Meditations is Marcus Aurelius’ private journal from his time as emperor, and is one of the most beautiful and wise books ever written. I can’t possibly do it justice. If you found this interesting, go and read that and some of the other real stuff. If you’re interested in modern takes and using Stoicism to help with stress and anxiety, I really loved the super short “Happy” by Derren Brown.

Until then, I wish you all the wisdom you need to qualify well, the sense of justice to sell with integrity, the temperance to keep your ego in check, and the courage to do all of these things even when they’re hard.