I Hate Disappointing People & It’s Time to Let It Go

When I started this blog a couple of years ago, I promised myself that I was going to be honest. If I couldn’t write honestly about a topic, maybe because it was too raw or too personal, or maybe because I only knew enough about it to be dangerous, then I was going to stay silent. Sort of like the “if you don’t have anything kind to say, don’t say anything at all,” mantra, but with an amateur-blogger-integrity-kinda spin.

I have respected this promise and still intend to, and yet, the posts that have pushed me the furthest out of my comfort zone have been the ones that have resonated the most with readers. You’ve crawled out of the woodwork to respond to my thoughts on relationships, personal crises, restlessness, and my complicated love for my country. It’s surprised me just how many of you have reached out after posts like these, only to share that you’re wrestling with a similar topic, or have struggled to find the right words to give context to your feelings.

At the beginning of this year, I promised myself (and you!) “more Grit, less Banter,” and so despite my squeamishness about baring my soul on the Internet, here I am.

To that point, I wanted to talk tonight about something with which I very much struggle, and for which I have very few solutions. I wish that I could give you answers and insight, but my hope is that this post will help us all work through our thoughts and hangups. So stick with me, kids, and let me know if you have any epiphanies along the way!

I’ve struggled with a lot of things over the years, but as I’ve gotten older and more confident in who I am, I’ve been able to shake most of them off. Even so – in spite of my convictions and contentment – I majorly, majorly struggle with disappointing people.

Put bluntly: I hate it.

In fact, I hate disappointing people so much that it often drives my decision-making in ways that aren’t always healthy or beneficial to either myself or the people I’m trying to avoid disappointing.

I constantly worry about letting others down, whether it’s as small as not finding a killer birthday gift for my best friend, or as significant as taking another job and leaving a team that I love. I even worry about not noticing when someone’s having a bad day and failing to be there for them due to my lack of awareness.

I so deeply hate disappointing people that I very rarely say “no,” and I often stretch myself too thin. I once sent flowers to friends when I got the stomach flu and had to cancel plans, as though it was my fault for getting sick! I recently had to turn down a request to volunteer somewhere – because I was already volunteering elsewhere – and it made me feel like a terrible person. Over the years I’ve purchased so many things that I don’t need or want, simply because I didn’t want to tell someone that I’m not into LuLaRoe or whatever the latest pyramid scheme may be, and disappoint them.

The thing is, disappointment is inevitable. I know this, because I wake up every morning hoping that I’m suddenly living at a cat sanctuary in Scotland and simultaneously running a DC-based nonprofit that brings people of all backgrounds together to have constructive conversations, and that J.K. Rowling is my BFF and we go to coffee once a week to discuss how to make the world a better place. I am unfailingly disappointed when I realize this is not the case, and that maybe my daydreams should be slightly less specific.

But in all seriousness, I’m no stranger to disappointment. I know that it is a fact of life. I know that it often leads to growth. I know that you can be incredibly disappointed, only to be grateful years later that things worked out differently.

Rationally, I accept that disappointment is inevitable, necessary, and sometimes a path to something better. And yet – I still feel sick to my stomach before I have to knowingly disappoint someone.

Why is this? Why can I not just embrace the freedom that comes with knowing that sometimes you have no choice but to let people down? Yes, I always want to be compassionate and considerate, and I’m not advocating that we all harden our hearts. But sometimes my fear of disappointing others is crippling.

I want to do everything, for everyone, all the time, even though I realize that’s impossible and insane.

I’ve tried to get better at identifying why I struggle with this so much, and I don’t have any good answers. I’ve tried to come up with some tactics to help combat my irrational feelings, and that’s gone a bit better. So, for all my fellow disappointment-phobes, here are a few tips that I’ve found helpful:

  1. Just (Don’t) Do It – I’m constantly pushing myself to say “no” to small things, so that when the time comes to say “no” to big things, it won’t be quite as difficult to do. The few times I’ve turned down plans with friends because I’ve been so incredibly overwhelmed with stuff that needs to get done, I’ve dreaded it. But then HOLY COW – the freedom of not running around a million places like an over-caffeinated lunatic! It’s priceless! My hope is that just like exercising, if I can build up my “no” muscles a bit, I’ll get better and better at it each time.
  2. Trading Places – I’ve also found that it’s best to try some mental role-reversal when I’m worried about disappointing other people. How often have I been irrevocably disappointed when someone forgets my birthday or reschedules dinner or declines to volunteer for something I care about? Literally, genuinely, NEVER. So if I’m not upset, why would they be? Trying to put myself in other peoples’ shoes really helps me gain much-needed perspective . . . there’s a good chance they might not even be that disappointed!
  3. Sometimes it’s Good to be “Bad” – You’re not a bad person for accepting another job, for breaking up with your significant other, or for recognizing and respecting your personal priorities. Avoiding disappointing someone in order to avoid feeling like a bad person is incredibly short-sighted! Sometimes disappointing someone you care about is ultimately in both of your best interests, even if it doesn’t feel like it at the time. Respect your own time and free will just as you would anyone else’s!
  4. People-Pleasing isn’t Sustainable – I am a natural-born people-pleaser. I want people to be happy, even if it comes at the expense of my own happiness. But sometimes this has led me to enabling friends’ and family members’ poor choices, or has resulted in bad decisions of my own. If you make all of your decisions in an effort to not disappoint people, one day you’re going to wake up to a life you don’t recognize, because it won’t be yours. It will be the life of the dozens and dozens of people you’ve tried to placate.
  5. Trust Your Gut – At the end of the day, you have to listen to that tiny little voice inside your head that sometimes gets drowned out by doubt and worry. If your instincts are telling you to do (or not to do) something, perhaps it’s time to tune in, even if the idea of breaking the news to the people you care about is terrifying. I often ask myself, “If I knew I wouldn’t disappoint anyone, what would I do?” and then the answer is much clearer.

It’s easy to sit here and type these “tips,” but I still have a physical aversion to the whole OMG-I’m-going-to-let-somebody-down process. I’ve gotten better at it the more I’ve done it, with less second-guessing and drama each time. I still have a longgggggggggg way to go, and I probably will never be immune to my fear. But as someone very wise once told me, “fear is temporary, regret is forever.”

Don’t let your fear of disappointing others drive decisions you’ll regret.

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