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Tough choices

We all have priorities in our evaluation of different aspects of life and business, whether conscious or subconscious. When we make decisions that respect those priorities, we tend to feel at peace. When we make decisions in conflict with those priorities, we feel that something's wrong. In some cases, being forced (by circumstances, someone, or one's own lack of awareness) into making such a decision can leave one very distraught.

Very often, the right choice can be found by simply "feeling" for it. You can rationalise it all you want, and even come up with elaborate, sophisticated and very convincing arguments for why it's right, but cheating on your partner (to take an obvious example) feels wrong, and that's your subconscious telling you this is not the right choice according to your priorities.

Unfortunately, life also throws much tougher choices at you. Making decisions is (comparatively) easy when there's a right choice and a wrong choice, but in many situations, it feels like there's no right choice - just wrong choices. In those situations, no matter what you do, someone will lose out on something and they'll be pissed off at you for making that choice. These are what I call "tough choices" - they're tough, because all the options feel wrong.

This happens particularly often in business. Tough business decisions are inevitable. Whether it's dealing with a fallout between cofounders, firing an employee that's not performing, negotiating a tough deal, or even assigning shares in a new business, businesses seem to have an almost magical way of providing an endless series of tough choices. To make matters worse, many startups are like pressure cookers that heighten emotions and drama and make all those decisions seem even more important and personal to those involved.

I've had my share of these tough choices (though there are no doubt many more to come), and I've come to realise that there are some very fundamental principles that can help with those situations.

1. Be aware of (all) your options

Most of the "tough choices" in life are artificially limited. "You have no other choice," says the authority figure in the famous Milgram experiment. "Oh, I have a lot of choices", replies one of the very few subjects who resisted this artificial narrowing of possibilities. Watch it for yourself here. It's inspiring.

Life and business throw many real "tough choices" at you, but the first thing you should do when faced with one is not to make a decision, but to see if the landscape of choices can be expanded. Many times, it can. In particular, it is always worth being suspicious of the menu of choices on offer, when it is offered by someone else. Chances are, consciously or not, the choices on that menu will be crafted to lead you to make the choice that someone else wants you to make. That is one of the most common ways that you can end up making decisions that conflict with your internal compass, and which you end up regretting.

Another factor that often limits our choices is our own axioms of behaviour. "I won't break my word" is a common one, which is easily discarded in extreme circumstances, but which we hesitate to disregard in normal situations. I am an honest and sincere person, but if I was in Nazi Germany, and an SS was asking where the Jews are hiding (and they happened to be in my neighbour's cellar), I would lie to them without hesitation and not feel bad about it. In more mundane situations, we tend to ignore this option of evading our own behavioural axioms.

Now, I'm not suggesting that breaking your word should become a routine, daily maneuver (though I'm sure some people will misunderstand this... this is the internet, after all). However, when you have really tough choices to make, I believe it's important to consider all options - including those that involve behaviours that you would not normally condone.

So, the first tool at our disposal is to reject externally and internally dictated set of choices and explore the full landscape of choice. This should be an automatic reaction to a situation where a tough choice presents itself.

2. Be aware of your priorities

The second principle is to be aware of what your priorities are. I'm not talking about your business priorities, or your priorities as an entrepreneur, though both of those matter and you should be very aware of them. Ultimately, however, you will have to live with your choices as a person, as a human being. So what are your priorities on a personal level?

Everyone will have a different set of priorities there, and the point is not to judge whether your priorities are what they should be (that's a whole different exercise), but simply to be clearly aware of what they are.

Are friends more important than business? That's an important bit of internal compass to be aware of when you start businesses with friends, because you will probably end up being faced with a decision that hinges on this question, some day.

Is creating value for customers more important than making profits? Are employees' livelihoods (if you hire any) more important than your own financial outcome from the business? Is your family more important than your employees? Is being entirely honest more important than closing the sale, or is it ok to be mostly honest? Is your health more or less important than your achievements as an entrepreneur? Would you sacrifice your life to make that dent in the universe?

There are many such questions that you can ask yourself. They're tough questions, whose answers will often determine your decisions when faced with a tough choice. Yes, they seem more personal than business-driven, but that simply reflects the fact that business is (for now) conducted by human beings, not by impersonal processes. You have to live with your decisions on a personal level, no matter how you may try to justify them as "just business".

Many may look at these questions and say "well, I don't want to make that choice - I value both family and employees", or "friends are just as important as business, I don't want to screw up either". Fine, tell yourself that if you want to, but that's just denial (similar to a product manager ranking all of 50 items on the development plan as "highest priority"). Some day, you'll be faced with a choice where either your employees or your family will be disappointed with you, where you'll either hamstring your business or your friendship, and then you'll have to choose one of the two.

That the choices will come is inevitable. What I'm suggesting is that by spending the time now, when you're not facing a crisis, to clarify what your priorities are, you will find it much easier to deal with the tough choices calmly, without panic, and correctly, when they do come.

A worthwhile exercise, then, is to try and figure out what are your top three or five priorities in life. What are the things that trump all others, and in what order do you place them? Having done this homework (and redoing it when you sense that your priorities have changed) helps in both personal and business life.

This is the second tool to deal with tough choices: be aware of your priorities in life, so that you can use them when making tough choices.

3. Erring on the right side

Sometimes, even though you're aware of your priorities and the full landscape of your choices, you might be confused about which choice best supports them. It might seem that all the options disregard your priorities equally.

When priorities fail, you can still fall back on universally accepted human values. Generosity, mercy, freedom, love, peace, life - those values (and many others) are universally accepted as good, and, should all other methods fail, falling back to them is a final safety net to make decisions that you can live with.

This might seem melodramatic, but it is a powerful tool when faced with the really tough choices.

If all the choices seem to contradict your priorities equally, which of the options is more generous, more merciful? If every decision is a mistake anyway, we can at least try to choose so that our mistakes lead us towards a better world rather than a worse one.

That is the final line of defence: if every choice is an error, we still have the choice to err towards good rather than evil.

In conclusion

I've proposed three principles to deal with the tough choices that come with every business. All of them start by accepting that we live with our decisions as human beings. "It's just business, it's not personal" is a fallacy. Everything is always personal to both the decider and the ones impacted by the decision, and recognising that leads to a framework that enables people to make decisions that they can live with.

The three principles are:

  1. Reject externally and internally dictated sets of choices and explore the landscape of choices on your own.
  2. Be aware of your own priorities in life, so that you can use them to guide your tough decisions.
  3. If every choice still feels like a mistake, err on the side of good, universal human values.

I hope you find this useful the next time you are faced with tough choices.

More from the library:
Startup sales: #6: Pre-qualification and triage
Stop looking for a cofounder
Internalising and externalising success and failure