David Strittmatter

Say yes to great opportunities (how & why)

If somebody offers you an amazing opportunity but you are not sure you can do it, say yes – then learn how to do it later! – Richard Branson


  • If I’m not a little afraid of my next step, it’s most likely too small
  • It’s natural to take risks
  • We need to find out what’s really valuable to us so that we can decide what to have and what not to have

Practical advice:

  • Ask yourself: What would you regret more in your 80s: Not doing it or doing it?
  • Adopt the right mindset: If you say no, you already lost
  • If you’re in doubt, say rather yes than no

Dear friend,

Recently, I faced a decision that will heavily affect my life:

I just started my career in strategy consulting where it’s not uncommon to work 60 hours a week. Before starting this job, though, I hadn’t only put many hours into my Youtube channel, Instagram page, blog, and TikTok but also had gone my first steps as an entrepreneur. Four other people and I built the foundation of a business and made our first sales.

At the beginning of this year, we sat down and discussed how far we want to go and how committed each of us was. Particularly, I needed to decide whether I want to sacrifice hours of the little free time that I had left to pursue this unpredictable journey.

In today’s blog article, I want to encourage you to make use of this kind of chances, write about opportunity costs, and provide you with the necessary toolkit to make bold decisions.

Why you should say yes

If you know me, you’d know that I wouldn’t say no to a great opportunity. I’m this type of person who sees the opportunity and not the problem. I believe that if I’m not a little afraid of my next step, it’s most likely too small. But you don’t have to be like a naive optimist to make a bold move.

It’s natural to take risks from early on: Life is about taking chances, and you begin taking chances from the time you are a baby. Taking the first steps can be scary, but then you learn that it helps you to walk and eventually run.

Unfortunately, as we grow up and gather more and more experience, we also become more and more risk-averse. Our decision making is often biased due to this extra knowledge. In making risky decisions, we often emphasize the importance of the downside risk, leading to an underestimation of the upside potential. Additionally, as the Nobel-prize winning Prospect Theory shows, we tend to experience a loss more negatively than a gain of the same amount – losing 20 bucks decreases significantly more our happiness than winning 20 bucks increases it.

Yet, risk-taking behavior allows you to feel a sense of independence, have a new experience, and establish yourself as an individual. While risks can be scary, they allow you to push past your perception of limitations and try something new.

By deciding for the venture and continuing to create content for the various platforms, I opened many doors and created exciting and lucrative challenges for myself. Even if the venture failed or worse, I was laid off by my employer for my bad performance, I’ll have experienced crucial lessons and wouldn’t have succumbed to my anxiety but lived the life I want.

Moreover, we need to remember that not taking risks is also a risk. When faced with a decision, realize that any road you take involves some risk. Even if that decision is to stay within your comfort zone or venture outside of it, there are risks associated with either outcome. When you stay within your comfort zone, you risk not experiencing happiness in different ways, not exploring more facets of who you are, and not growing in new ways.

Obviously, you can’t have it all

There’re articles all over the media debating whether it’s possible to have it all – whether it’s possible to be an all-star in your career and have a healthy family life and have cool and fun hobbies and be financially stable and have that sexy bikini body and …, all at the same time.

In my case, I want to do sports six times a week, build a company, grow my social media channels and blog, work as a strategy consultant, be a great partner to my girlfriend, sleep eight hours per day, eat healthily, spend time with my best friends, care for my family, and have some time left to learn new stuff by reading.

So far, it’s been working out pretty well, but there’ll be times when I won’t be able to have it all. Actually, nobody can always have it all. We all have to sacrifice something at some point. And that’s not bad at all but just right.

When we attempt to do everything just because the media, celebrities, or whoever postulate it, we won’t be happy but overwhelmed. Essentially, we’re then attempting to live a valueless life. When everything is necessary and desired equally, then nothing is necessary or desired at all.

Hence, we need to find out what’s really valuable to us so that we can decide what to have and what not to have. Even though risky decisions bring along uncertainty, clear values will help you to make good decisions.

But what should you exactly do when life offers you a great opportunity and you don’t know whether you should grasp it and take the risk?

How to decide

What greatly helped me to make this risky decision was my guiding principle: Every time I need to decide whether I do something or not, I ask myself: What would you regret more in your 80s – not doing it or doing it?

By taking the stance of my older self and thinking long-term, I minimize the number of regrets and make more profound decisions. When you think in decades rather than in years, taking risks is much easier. In 60 years, no one cares whether your startup failed, but you’ll definitely remember the day you said no to your co-founders and declined to grow that venture.

Moreover, making a bold move requires the right mindset: If you say no, you’ve already lost. Unfortunately, we often reject a great opportunity because we focus too much on the downsides and consequently don’t dare to take the risk. What we forget that everything great starts with a small step. If you don’t take this first step, you cannot win.

Finally, what should you do if you’re still not sure what to do? Since we all tend to underly biases amplifying the downsides and risks of an opportunity, I’d always say yes to something when I’m in doubt. From the day I clearly imagined the feeling of regretting something when I’m 80+ years old, the risk of regret clearly outweighs the risk of failure or overwhelming myself. Hence, if you want to minimize your regrets, always say yes when you’re in doubt.

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