Three Questions To Ask Yourself Before You Say Yes To Anything

Ihave a shocking confession to make - I am an optimist, not a pessimist.

This is shocking because a lot of the time I feel like a permanent pessimist and sceptic. I challenge norms, push boundaries, disagree openly and publicly and put myself out there opposing the common narratives.

I look at something and see the flaws in it. I read something and question if the source is honest, transparent and objective. I review a business plan, assume it will fail and then begin hunting for the points of failure. Perhaps it’s my journalism training. Perhaps it’s the fact that I am a nihilist and an atheist. Perhaps it’s just that I see the world for what it is while others choose to live in blissful ignorance.

Whatever the reason, I default to scepticism in most situations.

But the truth deep down in the crevices of my brain, heart and gut is that I am an optimist. I believe this to be true because I have trouble saying no.

Saying no is doesn’t come naturally to me. It’s a skill I have spent years developing and flexing. I often listen to people pitch an idea and think: “Oh shit, I can’t miss this opportunity. There’s something here and I gotta jump on it or I’ll miss out.” I then say: “Yes, sure let’s meet.” or “Of course I can help you.” When what I really want to say is: “FUCK NO! This idea is dumb, I don’t think it’ll work and you’re a terrible founder.” But I placate them and myself by diving in just in case there’s an opportunity there.

I believe that my default scepticism is an over-exercised muscle that I have needed to evolve to survive my optimism. I know in my subconscious that if I keep saying yes to everything I will never make any headway in life.

So I went the other way and became a mental grinch.

Looking back over a career of decisions, businesses, engagements, partnerships and choices I realise that I was actually unable to get my optimism under control. I say yes too often.

Recently I’ve taken a hard line with my work, my time and my choices. I default to no. My 2022 mantras include:

• More focus

• Fewer, bigger bets

• Move slower

• Be present

All of these involve saying no more often.

I needed to do this to save my mind from turmoil. I needed to do this because I am trying to focus exclusively on things that make me say “HELL YEAH!” (a mantra I’ve adopted from Derek Sivers). This extends deep into my life and as close to the edge as I believe is reasonable to go.

For example, I was meant to go to the dentist today. I don’t particularly mind going to the dentist, it’s not a fear of mine. But they only had a time that was inconvenient for me — a 75-minute drive there and back, no use of toilets at the dentist due to COVID restrictions after a long drive makes the anxiety palpable and I had a meeting shortly after that I was probably going to be late for because of the 9 am dentist appointment.

Photo by Jonathan Borba on Unsplash

Two things come to mind:

1. Why did I say yes in the first place?

2. Why would I go when I feel this pit in my stomach and it’s so complicated?

So I cancelled. I said no.

Going to the dentist isn’t a big decision so why should I agonise over it? Why would I commit to something so small and then force myself to do it even when it gives me physical pain in my chest just thinking about it? I wouldn't and you shouldn’t.

I have spent the past 20 years working hard to gain the privilege of one word; no. I have afforded myself the luxury to say no to things that I don’t want to do. The dentist is a trivial example that illustrates a broader point.

Success is a difficult thing to define but one of the benchmarks for success in my life is the ability to say no to things. The fewer things I am obligated to do, the more success I have achieved.

Think about the things that you have to do on a daily basis. How many of them would you choose to do again if you were just starting out? Would you change the work that you do? The car that you drive? The partner you have chosen? The pets that you have in your life? The place you live? The house you own? Would you say “no thanks” to any of them knowing what you know now?

Remember, you are not a tree. You do not have roots. You can move.

Ask Yourself These Three Questions

1. Will this make me happy and for how long?

I know that sounds selfish, but so what?

Going to the dentist will improve my life because the chipped filling will get fixed. But right now, it’s giving me a stomach ulcer thinking about the 75-minute drive there and back + the meeting I’ll be late for + the sore face + the traffic. So, it doesn’t make me happy and it won’t improve my life enough to justify the immediate suffering.

I still need to see a dentist so I’ll just book a new appointment at a dentist closer to me.

Some things need to be done and won’t make you happy. That’s OK. You have to figure out if it’s important enough to endure the unhappiness and then shut up and get it done.

2. Do I really give a shit about this… like, for real?

Excitement is contagious. When someone talks to me about something new, a business idea, a restaurant, a show, a band or whatever, I get excited because they’re excited. I jump in with both feet and I’m all like, “HELL YEAH THIS IS THE BEST THING IN THE WORLD.”

And then we part ways and I begin reading, researching and thinking more about the conversation and slowly I talk myself out of and away from their initial excitement because it’s their excitement, their vision and their enthusiasm. Not mine. It’s their perspective, their context and their insights for their lives. Not mine.

This happened to me with Web 3 recently. A lot of people I know are building businesses in the Web 3 and crypto worlds. They are leaving their careers and shifting their attention so I spent a few months reading before I let myself get carried away. I mark this as personal growth because ten years ago I would have sold my shirt to start building something in the new hot space. But I was calm, collected and measured and realised that there is always time and I don’t really give a shit about it right now.

3. Does this move me closer to my idea of success?

By saying yes to this big thing am I moving closer or further away from my defined idea of success? The first thing to notice here is that you need to have a defined idea of success and if you don’t, you need one. Stop now and think about it. Not someone else’s idea, not the fast cars, big houses, gold watches, expensive alcohol idea of success. No. Your idea. The comfortable, contextual and relevant version of success for you and those you care about.

If you say yes to building this business, marrying this person or moving countries does it move you closer to or further from your success?

BONUS: 4. Is this altruistic or selfish (for them or for me)?

I don’t believe in altruism.

I think that there is a self-serving benefit to everything we choose to do.

You give someone your kidney because you love them and want them to survive and you’ll feel good when they do and you’ll benefit from their existence. Sure, you sacrificed but it’s not altruistic.

So if you’re doing something because you believe someone else needs you to do it then you better fucking care about that person about as much as you care about yourself because doing things for other people exclusively is terribly difficult. It may not be tough in the short term but over a period of time constantly doing things for other people will chip away at your relationship with them. The best outcome is usually when both parties benefit in some way or another.

This will be different depending on who the other party is. In business, are you talking about your business partner and cofounder or competitor? Different outcomes lead to different feelings. In life, are you talking about your favourite sibling (I know you have a favourite) or a distant cousin three times removed? Different relationships and commitments lead to different feelings about the outcome.

Sometimes the best option is to be selfish because you may be a happier person to be around if you aren’t forced to do the thing that you hate doing.

Sometimes trying to be altruistic is the best option because it feels good to put other people’s needs ahead of our own and reap the benefits of that sacrifice.

But don’t fool yourself, every decision you make is a decision. You have agency and you exercise it whether you admit it or not. You are never trapped, you never have to say yes, you never have to do something you don’t want to do. You choose to do things and then you choose to be irritated and anxious about doing the thing you said yes to. You choose these things.

Choose better.