The Grief Nobody Warned Me Success Would Bring
The strange sadness that shows up right after you get the thing you prayed for – and why you’ve been hiding it.
I’m going to say something that I’ve watched some of the most successful people you can imagine only whisper behind closed doors, usually after a long pause, usually with their eyes fixed on the floor, usually prefaced with some version of “I’ve never said this out loud, but…”
Getting what you wanted can lead to grief.
It’s very disorienting. You hit the number, you close the deal, you get the recognition you spent a decade chasing, and instead of the arrival you were promised, a strange flatness settles over you. Underneath the flatness, if you sit still long enough to feel it, there’s actual grief.
What in the…?
How are you grieving while gaining? What I’ve found is that people don’t know they’re grieving.
They think they’re stressed. Overwhelmed. Burntout. In need of a vacay. Desperate for better systems. Just in a tough season. Whatever… fill in your blank here.
I’ll tell you about a client of mine whose name I won’t mention here, but she’s the real deal, success you’d assume was airtight from the outside. She had just closed the biggest, most career defining deal of her career, one she’d been building towards for years. She told me that the deal went through in one of our sessions, and I watched her face while she said it, and there was nothing there. No light. She may as well have been reading me her grocery list.
I asked her how she felt when it closed. She was quiet for a second, and then she said, “I felt like crying, and I couldn’t figure out why. So I just went back to work.”
I knew exactly what she meant, because I have been her.
I had my first million dollar year at twenty-eight. I’ve been in Forbes and Entrepreneur and Fast Company. I advise some of the biggest names in leadership. What I don’t talk about as much – although I am a lot more lately – is that a lot of that season felt hollow in a way I was deeply ashamed of. I would hit the goal, feel the flatness, and immediately assume something was wrong with me. What kind of ungrateful person claws her way up the mountain and then stands there thinking about the next one, because this one didn’t satiate, so the next one must be the one?
For years I thought I was broken. It turns out I was grieving and I didn’t have anyone I could say it to because I don’t think I really knew it at the time.
Here’s the cruelest part of this particular grief – it comes with a gag order. You can’t freaking tell anyone. The people below you on the climb would give anything to have your problems, and they’d be right to roll their eyes at you. The people above you have already made their peace with it or buried it deeper than you have. And the people beside you are all performing the same victorious highlight reel you are, so admitting the flatness feels like breaking rank. So you say nothing. You go back to work, like my client did. Like I did. You grieve in total isolation, which is the kind of grief that never actually heals.
Success shrinks the number of people you can be honest with.
I wrote a while back that success shrinks the number of people you can be honest with. This is the sharpest edge of that truth, because the higher you climb, the fewer people can hold what you’re actually carrying, until eventually you’re standing on a peak, but you can’t appreciate the view.
What is that? Why does that happen? What the hell are we grieving, anyway?
You lost the version of yourself that was still hungry.
There is a specific kind of aliveness that only exists in the pursuit. When you’re climbing, you are so awake. Every single day has a point and every decision matters because you’re building something that doesn’t exist yet. You know exactly who you are because you’re defined by where you’re going. The hunger governs everything – your calendar, your identity, your sense of purpose, your reason to get out of bed. You are, in the truest sense, on a mission, and a person on a mission does not have time to feel the void because they’re too busy filling it.
Then you arrive and the mission that organized your entire inner life just… completes. The scaffolding comes down and you’re standing there in the sudden silence of having gotten it, and for the first time in years there is nothing pulling you forward, nothing to chase, nothing to prove, no next rung with your name on it.
You’re grieving the death of the striving self. The hungry version of you who felt so alive is no longer necessary, because now all you’ve built needs a manager, and that manager is you.
So you went from dancing through the uncertainty of growth, taking risks that exhilarated you, to Zoom meetings, Slack messages, and tech hiccups. Like a drug addict coming down from their high, there you are, just maintaining.
But I have to go one layer deeper than that, because if I stop there I’ve only told you half the truth, and the second half is the part that actually sets you free.
The striving wasn’t only keeping you alive… it was also keeping you hidden.
This is the part I had to nearly die to understand, so I’ll just tell you plainly. When you are in relentless pursuit of something, the pursuit becomes a place to hide. All the learning, all the doing, all the sprinting…as long as you’re chasing, you never have to be still. And as long as you’re never still, you never have to face the deeper questions – the ones about whether this life is actually the one you were meant to live, whether the thing you’re building is even yours to build, whether you’d know who you are if you stopped producing for five minutes. The hunger doesn’t just give you a mission, it gives you an alibi as to why you aren’t who God’s calling you to be, yet. It’s a very socially acceptable, deeply rewarded, applauded-by-everyone way of running from yourself.
And then you arrive, and the running stops, and every question you outran for a decade is standing there waiting for you with its arms crossed, toe tapping, demanding answers.
That’s the grief. It was never really about the achievement going flat. The blah-ness is just the moment the noise stops and you finally hear the questions.
The grief of success is the terror of stillness.
I know this because I didn’t get to ease into that stillness. Mine arrived on an operating table when I lost more than half my blood and a part of me I’d built my whole identity around died in the most literal way it possibly could. The hyper-ambitious, productivity-fueled, always-climbing version of me did not get a graceful retirement. She bled out (dramatic, I know). And I have spent the last two years in the stillness she left behind, face to face with every question I’d been too busy and too impressive to answer.
It was the worst thing that ever happened to me, and yet, maybe also the most merciful. I think a lot about where I could have ended up had I not been gifted that wake up call.
The death of the striving self is not the end of your story, though! It’s the launch party to a new one – something even greater.
That hungry, climbing, proving version of you did her job. She got you here – she worked so hard, and she was running from things she didn’t even know she was running from, and she still built something, but she was never meant to be the final version. She was scaffolding, and scaffolding, by design, comes down once there’s something solid enough to stand on its own.
What God has been doing in the stillness – the stillness I fought and resented and wept through for two years – is building the version of me that doesn’t need the chase to feel alive. The version whose worth isn’t riding on the next achievement. The version who can be still without terror, because her identity is finally rooted in something the next accomplishment can’t give and the next failure can’t take.
You cannot get to that version of yourself without grieving the old one first. There’s no shortcut through it, at least not that I’ve found.
The fact that it hurts this much (or maybe feels like apathy) is evidence of how alive that old self made you feel, which means you’re fully capable of feeling that alive again, but this time just rooted in something that won’t die every time you reach the top of a mountain.
Just some food for thought today.
Love + prayers, Liz
