What’s the hardest thing you’ve ever had to do in your life?

I was recently asked, what’s the hardest thing you’ve ever had to do in your life? That’s a great question, because how we handle challenges and tough times is telling, in terms of who we are. Looking great while things are great, that’s easy; looking great when things are rough, that’s much harder. (I hope it’s obvious that with “looking great” I’m not commenting on how perfectly dressed or coiffed you are but about what kind of a person you appear to be.)

On the other hand, I felt the need to immediately go off-script and answer a slightly different question! Because I live for challenging myself, I routinely do hard things by choice. So there’s no one hardest thing. In different ways, for different people, I think that’s actually kind of common.

One-time events

For me: Physically, what’s the hardest thing? Here are some examples. I’ve climbed above 19,000 ft. Ask me again in a week and a half and hopefully I’ll have completed my first 100miler (so far, I’ve done 100K / 62miles). [Update: we’ve had to reschedule because my co-conspirator was ill.  Soon! This is a goal and not a limit – check out my view on limits that are not limits here. ]

Mentally, I’ve always challenged myself since I was young. Yes, I really did get two undergraduate degrees from MIT while working a full time job in my last 2 years. Morally, speaking out in the face of something that’s just wrong – requires courage. Big deal – I’m smart. I learn quickly. I can suffer physical hardship for a period of time. I got my warrior / protector genes from my mom (can’t argue with genetics).

Am I proud of having achieved these difficult things and of my hard work in doing so? Of course, I am! The point is these are one-time events. There are a lot of them over time, but each one is a separate choice. Sometimes the choices have consequences, sometimes not. However, each is a one-time event. Make the choice, take action, get it done – not so bad.

What’s really hard about life is making everyday choices that reflect true commitment to my values – e.g., mastery, protection of others, compassion. Being committed to mastering certain skills, for example, means I need to train every day, whether I feel like it or not, whether I ache or am tired or busy. It means I need to read and study even the boring stuff, even when I’d rather not. There is no one-time “I’m done now” box to be checked.

So, what’s the hardest thing? The daily stuff…

No matter what your passion, to truly move toward mastering it, there will be many hours where things really and truly suck. I love flying airplanes – but of course there are days when I think, man, wouldn’t it be nice to just sleep in. Yes – but that doesn’t make me a better, safer, and more professional and skilled pilot. Sure, working out in the cold and the dark sometimes hurts. But because I do it on a daily basis, it increases my level of mastery – and it makes the “big events” easy (well, easier).

Being compassionate and generous is easy when I’m feeling great. However, when I look in the mirror I can’t really give myself a lot of credit for that. If I’m truly committed, I need to be that even when I’m cranky and miserable or afraid – and whether I failed or succeeded yesterday I need to still do it today. The unsung, daily work, that’s the really hard stuff. Put in the hard work every day, and then when the big challenges arise, they’re not so hard.

Why is this so difficult?

Why is this daily stuff so difficult? Because there are no days off from these kinds of commitments. Going through the motions doesn’t count. Truly being my values, every day, not just wearing them like a coat when it’s convenient or fun, that’s what’s hard.

As always, I’d love to hear from you, what you think!


By the way, the title photo is not one of me – I picked it because it’s my kind of environment! It’s by Todd Diemer, on Unsplash. Thanks, Todd!