Perspectives: From burnout to breakthrough
How one solopreneur found the path that aligned with her values.
This issue of Perspectives is an interview with Maggie Blackburn. Maggie is an experience designer, career strategist, and coach living in Brooklyn, NY. After reaching a point where she felt lost, stuck, and misaligned with her life, she left the corporate ladder behind to pursue her own path. Now she designs retreats for companies and communities and coaches multi-passionate professionals to create careers that honor their multiple interests—not just one.
You can check out Maggie’s website, newsletter, LinkedIn, and Instagram.
This interview has been edited for length and clarity.
Anna Burgess Yang: Give me a little bit of background about your career. How did you get started?
Maggie Blackburn: I started my career in consulting. I had interned at Deloitte and then got a full-time offer after college. The first few years were pretty good. I was traveling and was excited about the work. But I got an itch to try something else. I was interested in marketing in college, so that’s what led me to work at Slack.
I was at Slack for about three years. When I first started, I really loved the product and the team. But during COVID, everyone started using Slack due to the increase in remote work. It was really stressful, and I burned out. There was also the Salesforce acquisition of Slack at the time. So that prompted me to think about what I wanted to do next and look for something else.
ABY: Was Slack fully remote at the time?
MB: Slack was fully remote in 2020, during the pandemic. Before that, I was going into the office in San Francisco. It was just a different time, pre-pandemic. My mindset was to climb the corporate ladder and get promoted. And I think after the pandemic, with working so much, I was asking myself, “What am I working for?”
ABY: What happened after you left Slack?
MB: I had this feeling that I needed to make a change, but I wasn’t there yet. The pain wasn’t enough. I thought I would try something else and learn new skills at another company within my product marketing role. But then, within the first few months at my new company, it felt like the job wasn’t what I had signed up for. I got a new manager, the product area I was going to work on changed, and leadership changed. So there were a lot of things going on. But in my head, I thought, “I can’t quit.”
ABY: What was your relationship like with your manager?
MB: My new manager started as a peer and then became my manager. So she was a newer manager. We didn’t really establish any personal rapport; our relationship was very professional and business-oriented.
A new VP of Product Marketing was hired, and a new role opened up on the team. He mentioned it during an all-hands meeting. After, he messaged me and asked me if I was interested in the role. I let him know that I would need to talk to my manager. I mentioned it to my manager, and she told me that they would need to post the role publicly for fairness. Shortly after that, I was told that the company wasn’t going to hire for the role after all.
However, I was told that the company still needed someone to work on the projects that the role was going to work on. So I was assigned to the work. I messaged the VP and let him know that I would be happy to work on it, but I would like something added to my current title to reflect it. After that, I met 1:1 with my manager. That’s when things started to unfold in a way I wasn’t expecting.
ABY: What happened?
MB: She pointed out that the company had recently had layoffs. She said that I was being ungrateful, asking for things. I wasn’t asking for more money — just a title.
The conversation felt like an attack. I was crying, and she was yelling at me. After that conversation, I didn’t hear anything from her. No apology, no follow-up. I asked for another conversation, and we talked again, but the trust couldn’t be rebuilt.
That conversation was what propelled me to do the work I’m doing now, as a self-employed person. But, at the time, it felt like rock bottom.
ABY: How much longer after this incident did you stay at the company?
MB: Two more years. I got a new manager. But there were so many changes at the company during such a short time. There was always a feeling that I needed to play politics or “play the game.” I felt stuck. I thought about trying to build something on my own and leaving corporate, but I was very scared of leaving the paycheck and financial stability.
ABY: How did you finally decide to make the leap?
MB: My first breaking point was that conversation with my manager, which propelled me to figure out what else I wanted to do. During that time, I was experimenting with marketing for small businesses or pivoting into events. A role actually opened on the events team at the company. I applied, but the manager wanted someone with more experience. That’s the second thing that propelled me. I realized that if I couldn’t pivot internally, it was time to actually leave and figure things out. Even though I didn’t have a steady inflow of clients.
ABY: What did you end up pivoting into?
MB: I pivoted into corporate retreats and different types of events. My very first project was with Julia Kaplan, founder at Recess, whom I’d met a few years prior. She asked me if I wanted to help her with a new project. She also ended up referring me to my career coach. It was very fruitful and full circle. And the event was really fun — we went to San Diego for a corporate retreat.
From there, it’s been finding new clients and word of mouth. A lot of it has been from LinkedIn. Even just by posting that I was leaving my job, I got another client.
ABY: What do you love most about running your own business?
MB: Definitely the freedom and creativity. I can launch a program if I want, or design my website, or play with social media, or work wherever I want. This past summer, I spent five weeks in London. No one’s telling you what to do. There’s not really a box that you have to fit in. Even if you are a creative in a corporate company, there are standards, and brand guidelines, and 1,800 approvals before your work gets out.
And being able to connect with other solopreneurs has been really surprising. People think it’s going to be really lonely when you go out on your own because you don’t have coworkers anymore. But I think you can build community.
ABY: What have you gained from working with a coach?
MB: I worked with a lifestyle coach named Alona Shaked, and now I’m working with Jenni Gritters, who is a business coach. With Alona, we did a lot of work around mindset. As I mentioned, I felt very stuck. I had no idea what I wanted to do next and had a lot of fear. The work was around challenging some of those thoughts. We looked at past examples of when things were hard, but turned out ok. It was a lot of visioning work.
I felt really misaligned and unclear about what I wanted to do. That part wasn’t necessarily the company’s fault. That was just me asking myself hard questions and working with the coach to identify what was important to me. Now I feel like I’m living toward my values.
At first, I didn’t even realize that having my own business and working for myself was an option. Then, for a while, I thought, “I’ll just do the exact same thing I’m doing in corporate, but work for myself.” But you can actually think bigger. It’ll take time to get there, but you can have a really beautiful outcome when you work for yourself and push through the discomfort.
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