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6 things I wish I had known when I started We Are Rosie

by | Feb 16, 2024

Stephanie Nadi Olson
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In honor of We Are Rosie’s 6th birthday, Founder Stephanie Nadi Olson peels back the curtain on her journey of entrepreneurship, the growth of the company, and what it’s been like to build a mission-driven business that’s reinventing how marketing works.

1. It will be harder than you think.

I often joke that if I had known how hard it would be to create We Are Rosie, I would have run for the hills. And I chuckle every time I hear the saying, “We do this not because it is easy, but because we thought it would be easy.” I certainly didn’t expect that changing the way work happens in the marketing industry would be easy, but I couldn’t have imagined how hard it would be. I definitely didn’t know what I didn’t know.

We Are Rosie sits at the cross-section of agency services, project-based work, consulting, and staffing. I had never worked in any of those sectors before. Eeeep! I had worked alongside many of those sectors, but I didn’t have a firm understanding of how they operated inside and out. On the bright side, this turned out to be a huge advantage. Without a frame of reference, I was unencumbered by hard lines about how things needed to happen. I hadn’t been indoctrinated into what was immovable and how things simply “just had to be.” This left me free to imagine a better way all on my own, which, as a creative, is a dream come true.

On the other hand, we had zero shortcuts—what we were building didn’t exist before we built it. We couldn’t copy someone else’s playbook because we intentionally set out to build a better way to do all these things: agency services, consulting, staffing, and beyond. No shortcuts means baptism by a million mistakes and a steep learning curve. It’s hard, but so rewarding as you make progress. Which brings me to my next point…

2. It will be more rewarding than you can ever imagine.

Building We Are Rosie is one of my life’s most rewarding experiences, right alongside being a mother to my daughters. At a high level, I’ve learned so much about myself, what I am capable of, how to push my own limits. But by and large, the most fulfilling part of this business is the people I’ve gotten to meet along the way and the stories from employees and Rosies about our impact on their lives.

We’ve had people tell us that through the project-based work opportunities we’ve provided, they were able to move out of a big city to take care of a family member who needed them. We’ve helped military families reunite by getting mom out of a mandatory in-office job that is states away from where dad is stationed. I’ve spoken to Rosies who had experienced so many demoralizing micro-aggressions in an office work environment that their anxiety was notably reduced when we gave them remote work opportunities. We’ve helped people who had faced age discrimination with full-time jobs find opportunities where their wisdom and charisma were valued.

These stories abound. And they are a constant reminder of why we do this work and how, even though we aren’t saving lives, we are lifting spirits.

3. People really show up when they see themselves in your mission and purpose.

Our desire to make work more compatible with people’s lives resonates with just about everyone. I’ve met very few people who can’t see themselves in this mission—who haven’t had a time in their career where they could have used flexibility in how they work. And for this reason, people from all corners of the industry have shown up for us time and time again.

They are people who possess decades more experience than me. They are people with so much to give, but who had (prior to We Are Rosie) sworn off ever working in this industry again for a myriad of reasons. They are people I admire deeply and people who have counseled me as an entrepreneur and as a human being trying to figure out this thing called Earth School. They are people I used to read about in the press who have now become my friends. And they are some of the most dedicated, caring, thoughtful teammates ever, who have shown up every day for six years, committed to making this industry a better place for everyone.

It’s not an accident that all of these folks have shown up for us. They’ve come because we’ve been willing to stand on our principles, even at the risk of alienating some people. I’ve always believed that you have to stand for something because standing for nothing is such a travesty (especially when you have so much privilege, as I do).

We’ve been bold. We’ve spoken out about what’s broken in the marketing industry. We’ve been unapologetic in our stances on social justice issues. We’ve been as authentic as we can be, and yes, we’ve made mistakes. But all of this, while it might turn some folks away, has been a lightning rod for bringing like-minded change-makers into our orbit. And that is the biggest reason so many people took a bet on a first-time entrepreneur who was disrupting three industries at once on a bootstrapper’s budget.

4. Everyone is figuring it out as they go.

I used to look at business leaders and think they all had something I didn’t have. A better education, more experience, bigger brain (!), and on and on. I used to assume there was some fundamental difference between me and them. And then I crowned myself Founder and CEO and found myself in the same room as so many of the people I’ve admired.

They are competitive, strong leaders, opinionated, and passionate. But I quickly realized that they didn’t necessarily work harder than me. They didn’t have some magic ball that told them all the answers. They, like me, were really good at doing the best they could with the information they had, and then figuring out the next best thing to do.

You see, we’re all figuring it out as we go. The world, especially the world of marketing, is changing too quickly for it to be any other way. And while I don’t necessarily recommend walking around shouting, “I AM FIGURING THIS OUT AS I GO,” I do think it’s important to give yourself permission to not have all the answers and to challenge yourself each day to find the next best thing you can do. One step at a time, just like the rest of us.

5. The flip side of the glory is getting your ass kicked every day.

So, there is a LOT of behind-the-scenes getting-your-ass-kicked as a leader. We don’t talk about it a lot because:

1) we know what a privilege it is to be a leader and no one wants to hear how hard it is to be in a position of power, and
2) it’s important to balance being strong (and engendering confidence in your team and customers) and being open and honest about things that are hard for you.

It’s a fine line.

I often describe my entrepreneurial journey as experiencing the highest of highs and the lowest of lows, sometimes within the same 10 minutes. The time I gave an amazing interview for the Inc 5000 and immediately after found out we had made a mistake that would cost the company five figures. The days when you finally get an MSA signed, but someone you care about deeply decides to leave the company. When you wrap up an all-hands call and are feeling GREAT only for your kid to look at you and say that you care more about work than them. It’s a lot. And it’s constant.

I don’t have a great lesson on this point other than to say that you really never know what folks are going through and you definitely only see the best parts on social media. And if you are an adrenaline junkie, entrepreneurship might be the career for you.

6. You can do it.

We’re six years into showing the world that by allowing people to work in flexible ways, your marketing will be more efficient, innovative, and inclusive. I’m really proud of the progress we’ve made on that point. I don’t think there’s a person in this business whose worldview about the power of flex experts hasn’t changed after working with We Are Rosie.

We’ve provided a community home for 30,000 people who’ve raised their hands and said they want to share their talents with this industry in a non-traditional way. And by eliminating our over-reliance on the record-of-privilege resumes that have long been the norm, we’ve created a way to match people with work that delivers better outcomes for clients and Rosies.

We’ve taken business from the biggest global players in the marketing space. We’ve collaborated with others. And we’ve provided our marketing experts to many. We’ve got Fortune 100 clients (lots of them!) who tell us they couldn’t run their teams without the support of our brilliant Rosies.

This is A LOT to accomplish in six years and I could not be more proud of the team, both our employees and our Rosies, that made it happen.

We’ve got a lot left to do, but at this rate, I think the flex all-stars at We Are Rosie will be the backbone of the entire marketing industry before we turn 10. I’m calling our shot.

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

Welcome to The Write-Up, a space for conversations about the future of work and flexible careers.

Whether you’re a CMO or an independent marketer (or both), we’re here to bring you bold perspectives, inspiring stories, and helpful advice from We Are Rosie's community of experts and thought leaders. Together, we're building a more inclusive, human future of work.

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