When Success Doesn't Feel Like Success

You know that feeling… When everything on the outside looks great, title, pay, team, all the boxes checked, but something still doesn’t sit right. 

Laura Gassner Otting has spent a lot of time exploring that space. First as a high-level executive recruiter, then as a bestselling author and speaker, and eventually as someone who helps leaders navigate the strange, quiet tension between “I made it” and “…so why doesn’t it feel like I have?” 

We invited her into a Blend conversation, and she got right to the heart of something many of us have felt—but haven’t quite known how to name. 

Success vs. satisfaction 

Laura calls it consonance: when your work aligns with who you are and what truly matters to you. 

Over the years, she has worked with many powerhouse leaders who, on paper, had it all. But behind the scenes, many of them felt restless. They had built their entire lives around what they thought they should want—only to realize, somewhere along the way, that they had stopped asking whether that version of success still fit. 

“We’re so good at chasing the goal,” she said. 

“But we rarely paused to ask, ‘Wait—is this goal still mine?’” 

The surprising downside of “making it” 

Laura’s book Wonderhell unpacked what happens after a big win: writing a book, landing a new role, hitting a milestone. 

Instead of feeling satisfied, you can feel... unsteady. 

Excited, but also anxious. Like there is more at stake now. 

Laura’s take? That was completely normal—and this feeling is a good sign. 

“Wonderhell is that space where you realize you are capable of more than you thought,” she said. “It’s uncomfortable, but it means you are growing.” 

It isn’t imposter syndrome. It’s ambition. And it’s messy. 

So how do you make success “yours”? 

With Laura, there isn’t a three-step plan or tidy formula. What’s so refreshing about Laura’s approach is that it isn’t about fixing anything—it’s about getting curious. Asking yourself: 

• What version of success are you chasing? 

• Does it still feel right? 

• What would happen if you gave yourself permission to want something different? 

The unpolished side of leadership 

At Blend, we’ve always been about these kinds of conversations. The in-between moments. The considerations you wouldn’t hear in a keynote, but that came up over coffee—or during a late-night scroll when you were wondering if everyone else felt this too. 

A final parting of wisdom from Laura was: “Success doesn’t have to be big. It just has to be yours.” 

This chat came out of Blend Book Club, where we invite people who challenge conventional thinking and aren’t afraid to talk about the messy reality of leadership. 

Want the full conversation with Laura Gassner Otting? Find it here: https://youtu.be/CiOX35Hk1fI LINK