Nice Work: Your career is more than a ladder

“I want to go where my leadership style is appreciated, not tolerated.”

Hey there,

You know how sometimes you meet someone new, and you’re immediately like, YES? That’s how I felt when I met Roberta Dombrowski.  

Roberta is a fellow coach with a UX background, so of course that’s part of it. But even more than her background, I clicked with her story. And I think a lot of you might, too. 

See, Roberta always saw herself as an ambitious person—someone who was willing to go the extra mile to get noticed and move up the ladder. And it worked! She moved from learning design and product management before finding her home in user research, and ultimately became the VP of user research at User Interviews. 

There was only one problem: all that success didn’t actually make her feel successful. 

Instead, it made her exhausted, anxious, and burnt out. 

I see this all the time in my coaching, too. It’s easy to spend years doing all the “right” things with your career: work at the most impressive companies you can. Angle for bigger and bigger titles. Put in tons of extra hours. 

Only to find out that the things that look good on paper make you deeply unsatisfied in practice. 

Only to wind up in an environment that doesn’t value who you really are—just how well you can stuff yourself into their mold. 

Roberta has those stories, too—like the time she was scolded for talking about hair products during a company retreat. It made her feel like it wasn’t OK to be a woman of color and a leader at the same time. “It didn’t sit right with me,” she told me. “I want to go where my leadership style is appreciated, not tolerated.” 

Those experiences—and the training she’s now completed on mindfulness and coaching—led her to take a different approach to her career. It’s one that’s counterintuitive to a lot of people. 

It’s about slowing down. 

“Many leaders talk about where they want to go and what they want to do. It’s all about making it to the next level, having an impact, or getting a raise,” she told me. “Only to find when they get there and take a step back, they don’t actually enjoy what they’re doing. I encourage leaders to just simply be present. When you’re present, you can connect with your values, and examine your work from different perspectives. You can investigate what you enjoy and why. Often your path may be something you won’t see until you slow down.” 

This isn’t always easy. Cultural norms often tell us that slowing down isn’t OK—that we’re only valuable when we’re hustling, striving, pushing forward. It takes concerted effort to do things differently. 

So over the past few months, Roberta’s been developing a new workbook designed to help people in the process. It’s called Consciously Crafting Your Career Path, and it comes out later this month.

We think more people should know about Roberta—and that a lot of you will want that workbook! So we’re putting on a free masterclass later this month to introduce you to her. She’ll share more of her story, give away some tools from the workbook, and walk you through an activity designed to help you slow down and get more mindful in your career planning. You’ll also get a discount code so you can grab a copy of the full guide! 

See the details below, and come hang out with us on August 24. I promise you’ll be glad you did. 

—Sara

Free masterclass

Why now is the time to consciously craft your career

August 24 from 1-2:30pm ET

If you're feeling disconnected, directionless, or burned out, don't miss this free masterclass with Roberta Dombrowski. She'll help you understand how old definitions of "ambition" or "success" might not be serving you anymore—and show you how to replace them with something more intentional instead. You’ll leave feeling energized to intentionally shape a career you can thrive in—one that is aligned with what matters most to you, not just what everyone else is doing.

On the reading list

The one question that inspires connection on teams
This bit stopped me in my tracks: “The radical part of radical self-inquiry is that we don’t do it. We don’t start off by saying: Here’s where I am . . . My heart is hurting. I’m nervous. I feel vulnerable. We lean into doing the work and the person gets dropped.”

Business Models for Freelancing in Tech
If you freelance—or want to—don’t miss this smart conversation between Laura Klein and Amy Santee on different pricing models and when and how to use them.

On writing the first draft of the Present Yourself book
Women Talk Design’s Danielle Barnes shares what it was like to write the “shitty first draft” of a book. The lesson: even people who write books about sharing your ideas with the world sometimes find it hard to share their ideas with the world! It’s not a sign your idea shouldn’t exist—it’s just human.