Abadesi Okunsade was born in New York and grew up in Maryland. Then, thanks to her dad's job, she found herself in an international school in Tanzania and exposed to people and cultures from all over the world.
Now she's the founder and CEO of Hustle Crew, co-host of the Techish podcast, Ecosystem Lead at Ordnance Survey, and someone who dreams of a future where women and other historically marginalized groups have more power, because the stories we pay the most attention to are of people who have the most power to tell them..
When Jill and I sat down with Abadesi, we had a candid conversation about assumptions, ambition, and why Gen Z might actually be onto something when they reject the old playbook. Here are three things we learned:
Abadesi has a rule she tells her team: assumptions are dangerous.
The less exposed you are to different cultures and different backgrounds, the easier it is to make those dangerous assumptions. And those assumptions lead us to create false stories about people. We make up stories and decide they're true based on nothing.
Abadesi's childhood taught her that you don't know what you don't know. It's incredibly easy to make an assumption about someone when all you've seen about them is one stereotype on TV, or something a problematic uncle said, or a joke your parents made. And you think, "Yeah, that must be true" because the people around you believed it.
But when you're exposed to different foods, cultures, languages, ways of living, you realize what you thought was universal is just how things are done in your house. Some people say grace before a meal, some don't. Some eat meat, some don't. And we shouldn't just give our respect or attention to people who feel the most similar to us.
We can allow our ignorance to make us feel superior. Or we can allow that ignorance to be a reminder that we really need more empathy and compassion.
Abadesi calls herself a reformed people pleaser: a middle child overachiever who wanted attention and approval. She recently spoke at her university graduation and was amazed that every single prize went to a woman. Best dissertation? Best student? All women.
Doing the work she does at Hustle Crew addressing salary inequities and inequities in promotions and positions of power, she thought, "Ten years from now, are these women winning prizes going to be paid the same as the guys in their class who weren't? Are they going to be in positions of power?"
The data tells us no. Women do really well in school because the rules are clear and we can people-please our professors. Then we enter the wild west of the workplace where every organization has its own unique culture, its own invisible rules that are always changing, its networks, its boys' clubs.
Abadesi now protects the boundaries that a younger version of herself would have felt guilty about. She allows herself to fail in situations where she thought it was important to win. Because we only ever have the information we have. We start a job excited and hopeful it's going to be what we envision. Fast forward six months, a year, two years and it might be a different management team or different culture. Suddenly, that dream to climb the ladder doesn't feel right anymore.
Abadesi gives herself permission to take the information she has now and move on. She's learned to give past versions of herself grace. The version she was six months ago did her best. Kudos to her. Today is a new day with new information. Six months from now, she might be disappointed in today. That's her problem. She'll deal with that at the time.
People pleasing is linked to control in a not-so-obvious way. It doesn't feel like it because you're giving your agency to the person you're pleasing. But it's also rooted in this belief that if you control their happiness, you can control how they feel about you based on what you do or say.
Abadesi's trying to humble herself about what she can actually influence and control. This isn't all about her. This certainly isn't everything she can control. So moment to moment: What can she own? What can she manage? And then she’s not too disheartened if the outcome doesn't pan out as hoped.
We asked Abadesi about "conscious unbossing," the trend among Gen Z that feels like a rejection of hustle culture and hierarchical power. She thinks about the socioeconomic context. Gen Z came of age in a specific time. A lot of them are still living at home; not out of failure, but because housing is unaffordable. Parents are stressed, supposed to be retiring or semi-retired, but they're looking after kids in their 20’s and 30’s and also elderly parents moving into care homes. Gen Z is watching this and thinking: What do I actually want out of life? My parents did well, but they look stressed as hell.
Then there are the stories on social media. People become millionaires by setting up supermarket challenges. Content creators are on the next richest of the rich list. How do you define that as a career? What's the career path to be a Twitch streamer billionaire?
The workplace has been completely deconstructed. The concept of a career ladder has been exposed and devalued. So a lot of people are thinking: I might just live at home as long as I can, travel every now and then, hang out with my friends. Things that used to bring shame — like living at home, which might have stopped you from getting into a romantic relationship — don't exist anymore if most people in your generation are doing the same thing.
Here's what leaders need to hear: Do young workers want to put their future in the hands of a manager who may not respect them, who might have problematic views about identity, capitalism, ownership? This is a conscious, intelligent generation with access to an incredible amount of information from day one.
So what can leaders do? Make the job (and more than just the job, the company culture) feel like something that can genuinely add value to a young adult's life. It's not just about the role. It's about how they're contributing to something bigger in terms of environment and society. It's about their growth potential, what skills or experiences they gain, what mentorship and coaching are available.
So much messaging in the corporate world is output-focused. A job description says, “you'll be responsible for A, B, and C,” and maybe 5% is "here are the benefits." That needs change. It should be 50/50. Fifty percent what we expect from you, fifty percent here's the pitch, here's what we're selling you as an employee brand.
Ask yourself: Where is that right now? If it’s absent, you have work to do.
After talking with Abadesi, Jill and I are thinking differently about assumptions, ambition, and what it means to create space for people to define success on their own terms. We're reminded that people are the product because there is no company without people. And we're reminded that even in the toughest times, we always have a choice. It might be deferred. It might be delayed. But it's still a choice.
Abadesi dreams of a future where more people, outside of just the default groups, get an opportunity to do something they've never done before. And we can empower that. We can help build this future of work.
It won't look perfect. But if we're willing to listen to women, ask them what they need, and actually act on what they tell us instead assuming, we might just get there.
Listen to the full episode of Work Made Human to hear more from Abadesi Osunsade about why women are told they've "ruined the workplace" (spoiler: we haven't), the story of a CEO announcing egg-freezing benefits when women asked for flexible work, and why the loudest pushback against progress often means we're getting closer to real change.