When to Say Yes


Among the swaths of online advice telling us how to live, there exists a wildly popular philosophy on how to best lead an enjoyable, adventurous, happy life. The basic idea is this:

We should say yes to every opportunity thrown in our general direction.

A chance to attend a 4-day music festival this summer? Hell Yeah!

An opportunity to backpack across Europe for 6 months after graduation? Absolutely!

Go out to a new bar with a group of people you vaguely know from work? Of course!

Attend an out-of-state university for the sake of being spontaneous and making memories? No-brainer! Yes!

Supposedly saying yes to everything leads to a meaningful and memorable life. But I would argue this is actually a terrible idea.

Surface Level Spontaneity

On the surface it seems that saying yes to any and every opportunity is an appealing idea. It allows us to be spontaneous and it opens up a world of new experiences and the chance to make lasting memories. At least that’s what we’re told.

See, after the excitement and adrenaline rush of saying yes to something wears off, we are left with facing the actual consequences of our choice. The reality is that saying yes to everything that comes our way can quickly lead to debt, poor health, and unhappiness in the long term.

After the initial week of bragging about attending an out-of-state school via social media, the student loans aren’t going anywhere. And they’re not quite as spontaneous and fun as we might have thought. Saying yes to going out and bar-hopping 3,4,5 days per week suddenly isn’t as great as we thought after spending half the week hungover with our wallets emptied out.

But I’m not here to suggest we should say no to everything and lead a mundane, predictable, mediocre life. Instead, I would argue that once you get really good at knowing when to say yes, life can be way more meaningful and exciting than you could ever imagine. So when is it a good idea to say yes? I use one simple rule of thumb to help me decide:

I say yes only if something threatens to push me outside of my comfort zone.

Saying Yes

When an opportunity arises that stirs up fear in me I have learned that it’s almost  always a good idea to say yes to that opportunity. Being fearful indicates an opportunity to grow and push the limits of my comfort zone. Steven Pressfield once said in The War of Art:

“Are you paralyzed with fear? That’s a good sign. Fear is good. Like self-doubt, fear is an indicator. Fear tells us what we have to do. Remember one rule of thumb: the more scared we are of a work or calling, the more sure we can be that we have to do it.”

Fear only reveals itself when we are presented with an opportunity that threatens to make us uncomfortable. The stronger the fear, the greater the opportunity to grow. Over the past couple years I said yes to many things that scared me, including:

Joining Toastmasters, a club that focuses on public speaking and communication.

hate public speaking. It terrifies me. I avoid it at all costs. So I joined a club where I have to speak in front of a group of people once a week and face my fear head on. Over the past three months I have had the wonderful opportunity of looking like an idiot on a regular basis in front of a small crowd of people.

But the benefits have been huge. I’m no longer scared to speak in front of a group and my confidence has improved significantly as well. Saying yes to this opportunity was initially terrifying but it has added tremendous value to my life and allowed me to conquer my fear of public speaking.

Traveling to Costa Rica.

The opportunity to do a study abroad program for 3 weeks in Costa Rica scared me. I didn’t know Spanish and I wasn’t particularly interested in making myself look like a fool attempting to communicate with the locals. So I said yes to this opportunity. I had an incredible time, met some amazingly friendly people, and experienced a culture that embraces slow-living and close-knit human interaction on a daily basis.

Of course I looked like a fool attempting to buy bananas at a farmer’s market when I only knew the word for ‘apple’. Of course I received stares when I was the only white male doing zumba in a public park with middle-aged Costa Rican women. But this trip taught me it’s okay to look ridiculous. It’s more fun to make a fool of myself than to constantly avoid doing things to protect my ego. This was a trip that I will truly never forget.

Traveling to Japan.

Similar to my Costa Rica trip, choosing to go to Japan for one month for study abroad was slightly terrifying as well. I didn’t know a single word of Japanese and I wasn’t particularly fond of seafood. There were many things that worried me about this trip. So I said yes. Again I met some amazing people who I still keep in touch with, I ate more seaweed than I previously thought was possible, and I learned that Japanese people are among the most humble and well-mannered people in the world.

Volunteering for projects that are over my head at work

I have been working full time as a data analyst for a little over 5 months now. As of recently I  have begun to volunteer for new projects, despite my lack of experience. Doing this often strikes fear in me. What if I fail, what if I can’t finish the project, what if I don’t know how to do something? I’ve learned that if I say yes I will figure it out as I go and I’ll develop new skills along the way.

That’s not to say I haven’t looked like an idiot or made mistakes, but I’m actually caring less and less about looking like an idiot for the sake of growing and learning. I’ve learned more in the past 5 months of my full-time job than I have in over 4 years of schooling. Saying yes to new projects that are over my head and beyond my level of comfort is scary, which is why I say yes to them. The experience I gain from these projects is invaluable.

Sharing my net worth online.

I debated for several months after starting this blog whether or not I should share my net worth online. I initially was held back by the fact that since I’m still at the beginning of my path to financial independence  it’s not even worth mentioning my net worth since it’s so insignificant. But I also realized that I was in a unique position to to share my financial journey from the very start and document the path all the way to FI.

I had to admit to myself that it’s not about me, me, me. It’s not about what people think of me or my net worth personally. It’s about my journey and being OK with the vulnerability that comes with sharing my net worth. I want to share my experiences, my setbacks, and my triumphs with others. I find value in documenting this journey, so although it’s a little scary I’ve deciding to say yes.

Choosing to say yes to opportunities that scare me has made me realize:

  • Most of my fears exist only in my mind.
  • The more I say yes to things that scare me, the more I expand my comfort zone and self-confidence.
  • It’s okay to look like an idiot, admit I don’t know what I’m doing, and ask for help. This is the fastest way to learn.
  • When facing my fears there is no room for ego.
  • If I try something and fail, I am the only person tracking my failures.


I have never regretted saying yes to any opportunity that has pushed me outside of my comfort zone. In fact, I’ve realized that a ‘comfort zone’ only exists in my mind and not in reality. 

So when you’re struggling with whether or not to say yes to an opportunity, first ask yourself: Does this scare me? Will this push me outside of my comfort zone?

I strongly suggest using free financial tools like Personal Capital to track your net worth, spending habits, and cash flow to help keep an eye on your money. The more you track your finances, the better you get at growing your wealth!

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5 Replies to “When to Say Yes”

  1. It sounds like you’re magnificent at looking like a fool, which is awesome! The War of Art is one of my favorite books, and I think about it every morning when I wake up and have to fight resistance against writing.
    I was honestly afraid to start commenting on other people’s blogs. This fear, as you mentioned above, is what pushed me to do it. I was worried that I wouldn’t add anything valuable or I would accidentally offend the writer. I eventually told myself “do it anyway, ” and now I use these three words to combat any fear I might have.
    Thanks for another terrific article!

  2. Hahahaha, that’s a fantastic point. I think it only makes sense to say yes if it … makes sense. It’s not always prudent to travel the world for 18 months if it’ll really screw you over. I’m finally at the point in my life where I could maaaaaybe get away with that, but still.

    It’s okay to be a free spirit, but know good boundaries for what’s adventurous and what’s stupid.

  3. Have you ever said yes and realised you didn’t really want it? I mean all the examples are that of saying yes and realising it broadens up your boundary after you’ve done it, haha

    1. Oh I’ve said yes MANY times and regretted it. I’m not saying there’s a way to always know ahead of time whether or not a situation will turn out favorably or end up broadening your boundaries, but in general when I say yes it’s because I expect to grow in some way because of that decision.

  4. Awesome stuff here Zach, you have wisdom beyond your years ;)!
    Derek Sivers has the saying ‘if it’s not a hell yes, then it should be a no’.. I feel that we’ve got a bit of a fomo mindset, even I have it although it’s a continuous evaluation to see whether there is balance in place or not..

    onwards and upwards man and loving your content!

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