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5 leadership lessons from my first 5 years as a founder and CEO

by | Feb 21, 2023

We Are Rosie Founder Stephanie Nadi Olson.
Image Credit: Photo by Brian Ingram
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So much of leadership happens when no one is looking. It happens in the time you spend bettering yourself to become the person your team needs for the next phase of growth. It’s in the effort it takes to reflect on an experience or situation you encountered for the first time, and how you might handle it differently if it comes up again. It’s tucked into the days that you do things that scare the shit out of you because you know that doing it will, in some way, help the team, the business, and the mission. I never could have imagined how all-consuming my own leadership journey would be. Like so many things with We Are Rosie, my leadership journey happened on hyperspeed, amidst crazy growth, an incredible pace of change, exhaustion, and pure joy.

Before I started WRR, I had worked as a “people manager” for less than a year. And I feel like I’ve gotten my MBA in leadership about a hundred times over since I launched the business. I’ve made some mistakes (many more than once) and I’ve learned a lot of lessons the hard way. Here are my top five take-aways on leadership after five years as a founder and CEO.


1. Spend time with people who have more leadership experience than you do. 

Some of my earliest connections and friendships at We Are Rosie were with people who have decades more leadership experience than me. I hired them, I asked them to be on my Advisory Board, I made them my friends, and I requested their guidance often. These were people with a leadership style that I related to and respected, so when I needed some help, I really leaned on their advice and experience. I made up for my own lack of formal leadership experience with theirs, and I used my intuition to decide which parts of their advice served me and which parts I could leave behind. It helped me form my own leadership style quickly.


2. No one else is going to set boundaries for you. 

This is one I learned the hard way, over and over. It’s not anyone else’s job to set boundaries around your time, energy, attention, and effort. And if you don’t set boundaries, you likely won’t have any and it will become very difficult to see the forest through the trees. You’ll be lauded as a leader who sacrifices everything, including themselves, for their team. And you will feel empty, weary, and eventually resentful.

Every time I hear someone describe a leader, almost always a woman, as someone that is everything to everyone—keeping all the plates spinning, doing the absolute most—my stomach drops thinking about how she must feel at the end of the day. The hyper-vigilance that requires. The exhaustion that follows. Because I know that feeling. Through panic attacks, deep fatigue, and burnout that led to depression, I learned that when you consistently abandon your own needs, your physical body falls out of harmony with your spiritual body. You’ll end up doing what you need to “get through” the days, not thriving but just surviving. And eventually, like me, you’ll crash hard. As a leader, you’ve got to start by loving yourself enough to set boundaries that will allow you to sustain the compassion, effort, and attention your team needs for the long haul.


3. Say the scary things out loud. 

Writing this piece, sharing some of the less-than-glamorous parts of leadership, is terrifying. But I’ve learned that courage is not the absence of fear. It’s taking action in the presence of fear. I share my story, as much as I possibly can, in an effort to make others feel seen. So many things are labeled as taboo or NSFW conversations, but it’s not realistic to expect anyone, especially leaders, to behave like robots devoid of human emotion and needs when they’re at work. My team (and the marketing community at large) has been so incredibly supportive every time I’ve shared the scary things out loud. When I tell them I’m not sure what to do next. When I tell them I’ve never encountered this challenge before. When I tell them I need a break or that I’m just feeling off kilter. They’ve never once made me feel anything less than supported. And I hope that it has given them permission to do the same for themselves. I am not a fearless leader. I am a leader committed to exercising my courage muscle as much as possible.


4. Managing people isn’t the only way to lead. 

Thank goodness, because there are so many incredible leaders on my team that do not manage a team. This idea that leadership only shows up when you have responsibilities for direct reports is as old-school as the 40-hour, year-round work week we’re seeking to disrupt at We Are Rosie. It relies on the idea of a hierarchical career path—that the only way to reach new heights at work is to literally “move up” the org chart. So many people aren’t interested in that. And judging by how many terrible people managers exist, not everyone is suited to do it either. I am thankful for the people on my team who’ve decided to lead as individual contributors. I am thankful we have a culture that allows them to be heard, their thoughts respected, and for them to have a career path that isn’t strictly up and to the right. Find and embrace these leaders in your organization early and often.


5. Be honest about when it’s your time to go. 

Last month, I stepped out of the CEO role and into an Executive Chair of the Board role. It wasn’t bittersweet or shameful. I didn’t feel like I was quitting. Quite the opposite, actually. I was proud that I had built a business that was so much bigger than me, the Founder, that it required someone with different experience and skills in the CEO seat to take it to the next level. The needs of the business, serving our core team of employees plus 25,000 brilliant freelance marketers, are so very different than when I dreamed it up 5 years ago. The operational complexity of the company made it clear to me that there was someone better suited to be at the helm as we move from start-up to scale-up.

I’ve seen a lot of founders and leaders stay in a role even though it’s no longer in their highest good, or the highest good of the people they serve. These leaders can undo years of legacy building by sticking around until they crash and burn. I think it’s a combination of ego (what will people think if I step away?), sentimentality (but it’s MY company or team!), pride (of course I can figure this out!) and comfort (but what else am I going to do?) for most people that hold them in a position past their prime. But I think one of the greatest signs of a leader is to know when their time has come and to be brave enough to say it out loud.

As we begin our celebration of We Are Rosie’s 5th year around the sun, I am so thankful for everything this journey has taught me about leadership. The rewards earned, the lessons learned, absolutely all of it. It’s made me a better person, parent, friend, partner, and business person.

Founder of We Are Rosie | Follow Steph on LinkedIn, Twitter, and Instagram

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