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You Didn’t Fail Just Because It Wasn’t Hard

The “I didn’t work that hard for this thing to happen so I didn’t really earn it” conundrum.


I received an email from a fellow business owner and dear friend yesterday, someone whom I adore, who has helped me when I’ve been lost in the pits, directionless, overwhelmed. Who has laughed with me over margaritas, helped me try to choose joy and fun and creativity, and let me cry and rage when I’m still lost.


Her email floored me because it was so vulnerable, so honest, such a brave pulling back of the curtain to reveal what, I truly believe, so many women have done and also believe.


We are not good enough to do the hard thing, so we do something easier; and when we do that part well, we believe we still failed - are failures - because it was the easy choice, and we knew it was the less challenging road.


Meg said this in her email:

In art class, we’d usually have some kind of still-life week...And every time, every SINGLE time, I had a clever trick. I’d focus in REALLY tight on one area of the still-life. One statue head. One point of a starfish. One zoomed-in area that I knew I could recreate pretty easily.


The art teachers always thought I was being edgy. Like I was breaking the expectation of the assignment and doing something new and cool but… I wasn’t. It was the same trick every time. And I did it because I genuinely didn’t think I could face the whole still-life. The bigger picture with all its details and things I could get wrong was SO overwhelming that I just… didn’t try.


And that’s just one example out of MILLIONS of times that I told myself this same story:

That I’m not good enough to do the “hard” thing, so I’m not even going to try.

That what I could do was easy and obviously, therefore, a failure.


There are very few things in my life that I could say I was genuinely proud of, because, invariably, I always knew, deep inside, that it could have been more. I could have set the bar higher and done something REALLY impressive but… I didn’t.”


If you’re nodding your head, you’re in the right place, in excellent company. I am so relieved to know that I am not alone in this behavior, this pattern, this belief.


Here’s what I responded to Meg:


We’ve been indoctrinated intensely that if things aren’t hard, we’re not doing enough; or if we enjoyed them and they were easy, we were failing.


I used to wait until the night before papers were due in college, every time. My roommate and I had a running joke about it, because every time, we’d get As.


I assumed it was because the school wasn’t hard enough, or the teacher wasn’t reading closely enough, or that I was somehow still not really deserving of that grade.


My friends from high school mostly went to Ivies, and here I was, cruising through my favorite classes at a decent college, but certainly not working “that hard.” Or “as hard as I could.” The classes I didn’t like, I didn’t try as hard, and my grades showed there, but oh well. Whatever - I couldn’t bring myself to care.


Could I have gotten a tutor? Sure.

Have I used anything from those classes since? Nope.

Do I still have stress dreams where I’m not sure I actually had enough credits from those classes to graduate? Yup.


And I’m doing just fine.”



I recently explained myself as a survivor of burnout, of prep school, of being a New England WASP, of growing up as a feral farm kid, of self-imposed and deeply influenced sky-high expectations. In reality, I should say I’m more in recovery from these things: like with other addictions, I am always slightly more at risk of falling back on these habits than of abandoning them entirely.


Instead of celebrating that I was doing well in school, I assumed the school wasn’t hard enough.


Instead of enjoying, appreciating, or heck - intentionally choosing to take the easier path that would not result in stress-induced health issues, I simply assumed I wasn’t good enough.


As if being more stressed, more anxious, more overwhelmed, or more dedicated would have meant I was “doing college right.”


Spoiler: I now have intimate knowledge of working (almost...yikes) as hard as I could, of scoring 20/21 on a medical anxiety screening, of sobbing while walking my dog, of burning out completely and I did not, in fact, gain anything more from that process than if I had taken an easier route.


I certainly learned things, and I pivoted into a business and practice that I thoroughly enjoy now; but who is to say that I wouldn’t have come around to those anyway, at some point?


Why must we believe that suffering and doing things the hardest way possible is always right?


Do I believe that hiking a mountain for the view makes you a better person or builds more appreciation than taking a helicopter to the top for the same photo op?


Not really. I think you’ll learn different things on the way. I’ve done intense hikes and been too grumpy, sore, or tired to appreciate the view; and I’ve been helicoptered to a glacier, which was one of the most magical moments of my life.


I would love to unlearn and release the guilt of taking the easy path, to recognize that there is beauty and worth in allowing yourself to work less and live more.


Because, when I look back on my college paper writing or Meg’s still-life micro-focus, chances are that, instead of doing intense work, we were doing other things that brought us joy.


I was absolutely reading, writing for fun, laughing with my sorority sisters (with whom I’m still very close, which I cannot say for my logic class or astronomy lectures), healing from a break-up, or exploring the local haunts.


Taking the easy path does not make us failures or less worthy of success. It allows us to experience more, which I think is the actual point of our journeys on this mortal coil.


Prompts for Your Reflection:

  • When have you taken an “easier” option? What did you do with the extra time, energy, or space it gave you? How do you feel about that choice now, compared to then?

  • How do you personally define “easy” and “hard”? Where did those definitions come from?

  • Is there room for joy, meaning, or growth in both the easy way and the hard way?

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