Maggie and I met a few years ago - having been ships in the night at Salesforce x Slack and both burnt out from tech. Just generally not feeling heart-centered in a place where most (or what seemed like most or even all) felt secure and “happy”. Why weren’t we feeling the same way?
Fast forward a couple of years and my life has changed. Work for me is not a job, it’s an integrated part of my life. And not to speak for Maggie, but I think she feels the same way being a career coach and fractional marketer. Our threads continue to tie together as we build our businesses around experiences. Every week she drops stories, insights and more in her Feeling Free Newsletter. It just so happened that last week, she dropped my story. Thank you so much for sharing my story, Maggie!
Melissa, thanks so much for chatting with me! For over a decade, you built a career in corporate tech working at big brands like Facebook, Salesforce, EA, and Hootsuite. What did that chapter look like?
That period was wild. My ego was heightened the more I was hired by the big names. I experienced a sense of professional validation and felt like I’d made it into some kind of “in” crowd.
But I started experiencing imposter syndrome. Being in such large organizations meant the death of the generalist, and there was pressure to specialize. This chapter also coincided with my move to San Francisco from Vancouver, getting married, and starting my family. My sense of self-worth shifted more toward personal life than professional identity.
During your full-time job, you also got into voice acting and cupcake baking. How did those come to be?
With the lack of finding and fulfilling a sense of identity tied to work, I stretched myself into personal passion areas. I worked with voice actors early in my tech career—many of whom were incredibly talented and felt like versions of me: people putting on a mask for work. I had grown up as a performer, so stepping into that persona felt natural.
For one of my birthdays, my parents gifted me baking classes at the San Francisco Cooking School. When I’d witness my kids’ birthdays with crazy-flavored specialty cupcakes (that weren’t cheap!), they were just licking the icing off and taking one bite. I knew there was an opportunity gap in the market. I passed along my love for baking to my kids, thus Simple Cakes was born.
Melissa enjoying a slow visit to a cafe with the freedom of her non-linear career.
When did your full-time job start to feel misaligned? Was there a specific moment that made you want something different?
It was re-org number two in the year. I found myself stuck as a senior manager, with a knot in my stomach going into the workday. I had a manager who hit my biggest “I am not enough” trigger with every small interaction.
I was working in such a silo—physically and within the team—with this illusion that we’re plugged in and essential to the business. I felt so heart and head misaligned.
Did you have any fears when leaving corporate to venture out on your own? How did you overcome them?
Absolutely. I had been the breadwinner in my relationship since day one and with over two decades working in corporate, I didn’t know how I’d navigate without the stable rug of that W2 under my feet. I didn’t overcome my fears… yet. I am working on them daily. While yes, the lack of a stable paycheck is a huge fear, for me, a big fear was this gigantic task of building something as big as Facebook and the like.
I thought that I needed to be in the big boardrooms to make life-impacting changes or own multi-million dollar marketing budgets to be innovative. Now being a Realtor, I am amazed and find it so incredibly beautiful how other people work hard to live their life to the fullest.
Why did you decide to become a realtor?
I knew I wanted to do two things: help as many individuals as I could with life-changing impact and make things beautiful. Sounds simple, yet it was a big, juicy existential crisis.
I found myself exploring financial advising, writing a book, and developing a short-term rental investment plan with my partner. I danced, I surfed, I returned to many interests that were a huge part of me growing up. A lot of what I explored sparked me, yet they began to lose steam.
It took me four months of this solo exploration before I spoke to my mentor/realtor, which opened my eyes up to entrepreneurship in real estate.
Melissa celebrating being featured in the Good to Be Home Magazine!
What has been the biggest unexpected joy of running this kind of portfolio career, and what’s been harder than you expected?
I truly can do whatever I want! No one is stopping me, no one is truly getting in my way. I am capable, I am enough, and I continue to remind myself of this.
I didn’t expect the unlearning of working in corporate to be so intense. As a licensed Realtor, building your own business and practice within these walls is such a trip. You’re on your own and you are your own small business, but it’s structured like a corporation? Yes, that is how the system of real estate works. So for me, making decisions and discovering my solo negotiating power within this system has been a wild ride.
How do you manage your time and energy across so many different things?
Boundaries are our friend. Working weekends for open houses or client tours has been a challenge for my family. So shifting my weekday boundary for a R&R day for myself or Saturday morning boundary, so I can make it to my kid’s soccer game has been a lifesaver.
I’ve also joined a hula school, where I treat weekly adult hula classes like church. I am there–tired or not tired, late or on time. It is my time to connect with myself and my hula sisters.
What’s one thing you believed about careers or “success” when you were climbing the corporate ladder that you’ve since completely let go of?
Time is the greatest resource of all. You can’t get it back. The flex of busy-work is entirely gone for me. I used to hand-make so many spreadsheets and reports and trackers, now I get AI to do it.
How do I make the most impact on my business out of this bucket of time? Because it’s the only time I got!
What are you most excited about building or exploring in your business in the next few months?
I’m taking staging and interior design classes to extend my real estate service offerings. Not only do I love sharing my style and my desire to make things beautiful with others, it’s also going to fulfill my creative cup.
I’m also super excited about starting my short-term rental investment portfolio with my partner. When it all comes down to it, I define myself as an experiential designer and to me, these vacation rentals are a complete and whole expression of that.
Where can people connect with you and learn more about your work?
I’m Melissa, a residential real estate professional serving Oakland, Berkeley, and the broader East Bay. If you’re buying, selling, or just starting to think about what’s next — I’d love to talk.
