When Success Isn’t What You Thought It Was

It’s okay if success is feeling a drag

Susan Doerksen Castro
4 min readMar 29, 2023
Photo by Johnny Cohen on Unsplash

The verbal grind of a 15 year old professing he hates school is getting old. While it’s age appropriate behaviour, the repetitve chant of “school is so boring and useless” and the endless asking of why he must study Shakespeare and how is THIS going to help him? makes me want to lock myself in my closet.

And, I feel his pain. While 50% of the time I’m rolling my eyeballs and clenching my teeth as I hear the drawl, the other 50% of the time I remember the arduous task of memorizing an endless list of biology definitions… mitochondria, anaerobic respiration, glycolosis etc. Why??? Oh the torture.

You’d think that the kid would remember all the things that are going well him right now.

But of course, right now he can’t see that.

School sucks.

Do you ever feel like this?

Like everything has gone to (or is) shit and if we could just toss it out on the curb and request a do-over all would be well?

When school (or success) sucks

As I see my son in a tailspin of despair, I can, with compassion see how his experience, for him, is real and true.

The utility of his present experience is unavailable.

At this stage in his life, I don’t really need him to “like” school, but I do want him to be curious.

So when my more patient self is accessible, I ask him to tease out what he does like to learn about (and why), who his favorite teachers are (and why), and to know which subjects he despises (and why).

Because sometimes things suck, and even what sucks can teach us something.

Lest you think this is a glass half full approach — it’s not.

We get to fiercely dislike some elements of our life.

I want M to cull out what he truly dislikes (and be okay with it). Not to stew in negativity nor whine, rather to see how even this part of school is teaching him something.

Yes, all the things he dislikes, some subjects, how some of his teachers teach, how the day is set up, all of it is grounds for helping him learn about himself.

This is the thing I never did. My approach was to grin and bear it, try to find the silver lining, or find a way to like it, or feign liking it. Or get another perspective, or ask for advice — anything to just try to like it.

Until I got to a part of my life where I just couldn’t like it all anymore.

It’s okay if success is feeling a drag

While this might not feel comfortable, it’s okay to declare that your current version of success isn’t feeling great.

What if instead of aiming for being positive and grateful and glass half full you get a wee bit more honest and declare “Nope, this (INSERT THING YOU’RE TIRED OF) ain’t for me anymore.”

You already know how to be positive and grateful!

If you’re looking around and feel significant dis-ease about the success you’re in and it’s just not floating your boat, it’s time to name that. It’s time to rant, mad scrrible in your journal, vent to your bestie on a walk or two, cry, pound the pillows, and be pissed about it.

And don’t expect that one session will suffice. More is better here. And expect it to feel cathartic. Yes, allow the feelings to flow flow flow.

And just because you feel crap about it all, doesn’t mean you’ve taken a wrong turn, or made a mistake or were asleep at the wheel of your life. None of that. It just means that you’re not loving it any more.

Why it matters that you hate this (version of) your success

All these feels are a part of letting go.

Naming what’s hard, seeing it, feeling how it’s no longer you.

Don’t skip this, nor avoid it, just know there is big and juicy energy in these uncomfy feels that can be unlocked, and all this yuck is a minefield of insight into what matters to you now.

That’s right — it might look like dirty sooty coal but it’s also where you’ll find the diamonds.

Should I stay or should I go?

Often times, women will ask me if they should quit their jobs when they get intimate with their feels and yuck.

I remind them it’s always an option.

But I’d encourage you, before going any new/ different route, to examine what you’re disliking fiercely, feel into it and allow it to uncover what’s true for you now.

All to say that a job change isn’t going to uncover what success means for you now. Only you know this about you.

Because just like for my son, while he (thankfully) doesn’t say he’s quitting school, it would be a loss if he didn’t see what school is teaching him beyond the content. This chapter of life is also teaching him about him.

After you have your scream fest

(Yes, I’ve had in car scream fest sessions), get curious. Notice what’s left behind that isn’t shit, notice that you may feel a little less connected to what you’re disliking, and notice there may be more room to be curious about what will make your heart beat a little harder.

To our shared new way of success,

Susan xo

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Susan Doerksen Castro

Entrepreneur & Integral Master Coach™ helping accomplished women redefine success so they can realize a new, more fulfilling agenda for their lives.