Trusting Your Career Trajectory

To freelance, or to full-time? 

In this week’s edition of The Zap, we sat down with Alana Mairs, a seasoned marketing professional, to discuss her career journey and the pivotal moments that shaped her path. 

Her story is one of trusting the process, even when the road was unpredictable.

Kaley Ross: Hi hi! How are you, how's the island?

Alana Mairs: So nice to see you. The island is good. 

Oh my god, are those your cats in the background? 

KR: Ahaha yes, it’s zoomy hour. They will be scampering about for a bit. 

AM: Love it. 

KR: Thanks so much for doing the newsletter! 

Let's start at the beginning. When did you decide to pursue a creative career, and how did that journey start?

AM: I love this question! Honestly, I didn't consciously decide to get into marketing. I knew I loved writing and editing, and I accepted my first job as a web editor at a software company called Business Objects (now SAP). 

I ended up on the web marketing team, and that’s how I discovered my passion for marketing. I loved using communication skills to connect with and build communities, but it wasn’t something I planned—it just happened!

KR: That’s such a common theme! A lot of marketers, myself included, kind of fell into this career by way of following their creative interests. 

Was there a moment where you realized, "This is it. This is what I’m meant to do"?

AM: There wasn’t a single “aha” moment, but there were several key experiences. 

One was when I joined lululemon. At the time, lululemon was small—our web team was just four people. Being part of such a fast-growing company, I was thrown into so many exciting projects. 

Looking back, I can't believe the level of trust and responsibility they gave us. It was a time of incredible growth, and it confirmed for me that this was the right path. It was a crazy but magical experience.

KR: Yeah, such a special time to join the company—those types of roles at that kind of company I feel are like, once in a career type opportunity. I love how you said it felt magical. 

Did you have any mentors during that period who played a significant role in your career development?

AM: I’ve been fortunate to have several mentors throughout my career, especially during my time at lululemon. There wasn’t one person, but rather a collection of people who shaped me in different ways. 

Even those I don’t consider mentors or vibe with as much had an impact. They taught me valuable lessons about leadership and trust—how I want to show up for others and what kind of leader I aspire to be.

KR: That’s a great perspective. Shifting gears, was there ever a moment where you felt like everything was falling apart, and how did you navigate that?

AM: Oh, definitely! In 2013, I quit my full-time job at lululemon without having another job lined up. It was a bit of a leap of faith, and there were moments where I thought, “What am I doing?” 

But I trusted that things would work out, and they did. I ended up freelancing for two years. One of the first people to reach out to me was a yoga ambassador I had worked with at lululemon. 

From there, word of mouth spread, and suddenly, I was a full-time freelancer. It wasn’t planned, but it was an amazing learning experience.

KR: I love that. It really shows how trusting the process can lead to unexpected opportunities.

AM: Exactly. I think trust is the theme here—trusting that things will work out, trusting yourself, and trusting the people around you.

KR: As a marketer, what lights you up the most? Where do your strengths lie, and what do you love sharing with the world?

AM: My strengths definitely lie in storytelling—creating a connection between the brand and the community on an emotional level. 

I love building the story of who a brand is and what it stands for, making people feel connected to something beyond just a product. 

I’d say I’m less of a technical marketer, which is something I’d love to work on to become more well-rounded. 

But what really excites me is the emotional, people-driven side of marketing.

KR: I completely relate to that. I’ve sometimes felt, not exactly insecure but perhaps like I was behind in my experience, about not being as strong on the technical side. 

But I’ve realized my natural strengths are also in the brand and community side—the emotional and storytelling aspects are just as crucial in marketing. 

When building out a whole marketing team, it’s all about bringing different strengths together.

AM: Exactly! Every marketer has their place, and each strength brings something essential to the table.

KR: So, you’re currently at Shift. Can you tell me more about that?

AM: Shift is a tech company that makes a power browser, helping people integrate all their apps and extensions into one window. 

It’s a small but passionate team, and I love the startup vibe. Everyone’s really excited about what we’re doing, and we’re driven by our core values, which makes the work feel meaningful.

KR: That sounds amazing. How do they foster that kind of culture within the team?

AM: We recently rolled out our company values, so now we’re integrating them into our day-to-day, like in our one-on-ones. It’s a great way to ensure we’re living those values as a team, even though I’ve only been there for a few months.

KR: Speaking of exciting projects, I’ve heard about Shift’s digital nomad campaign, where you’re giving someone $10,000 to work remotely, anywhere in the world for a month. 

Can you share more about that?

AM: Sure! We noticed that digital nomads were one of our core user groups—they often juggle multiple accounts and applications. It felt natural to create a campaign specifically for them. 

It’s been a fun project, showcasing both the product and the adventurous, travel-driven lifestyle of nomads.

KR: That sounds so fun! I love that idea for a campaign. Such a creative way to weave in an influencer vibe but in a way that really connects with a core user of the product.

Now that you’ve been climbing up “Career Mountain,” as I like to call it, for a while, what are you most proud of, and what’s your vision for the future?

AM: I recently reflected on my career journey, and I realized my path has never been linear. 

I’ve followed my gut and heart, which I’m really proud of. It might not have made sense to others or myself at the time, but looking back, all the dots connect. 

As for the future, I’m really enjoying the "mountain" I’m on right now. I’m excited to see what’s next, but I’m also content with where I am.

KR: I love that! 

Finally, if you could give one piece of advice to someone just starting out in their marketing career, what would it be?

AM: Be open to trying different things and really listen to yourself. Say yes. Pay attention to what lights you up because that will guide you in the right direction.

KR: Such great advice. Thank you so much, Alana!

AM: Thank you! This was so much fun.

⚡️ Bonus Round

KR: You’ve had periods in your career of both freelancing and full-time at global and national brands. I know you said the first time you went freelance you didnt have anything lined up, but how did you do things differently at other times to prepare for each transition? 

AM: Great q! Staying connected to my network is what helped me in subsequent periods of freelancing. A community works because it’s about both giving and taking. If I have advice, feedback, or can make an introduction to help someone else, I will. And subsequently, when I’ve needed the same during career transitions, other people have supported me in finding my next move.

KR: How do you prepare for interviews at companies after a period of freelancing to stand out? What advice would you give someone looking to get back into a full-time gig after they have been freelancing for a while? 

AM: Practice telling your story out loud to yourself, your cat, a supportive friend. Distill your experiences down to the ‘why’ behind every choice, and reframing things that may not be obvious to someone reading your resume without the full context.

KR: What resources would you recommend to someone looking to follow your footsteps?

AM: This may not be the answer you’re looking for, but I think it’s really important for creative marketers to understand what’s motivating to them outside of work and what keeps them energized so that they can approach work with a well-rounded, fully-charged self. 

For me, movement is key - e.g. a good workout (big fan of Jaybird), a hike with a good snack break at the top, a long walk with a good playlist - help me get out of my head and listen to my gut.