For the second story in our BOSSES series, we talked with our good friend and mentor of all things marketing, Lena Milcarek.

Lena’s a self-employed digital marketing specialist, Connecticut resident, tarot enthusiast, and BOSS. This comes after 11+ years of experience working in e-commerce and software. Surviving massive acquisitions and company restructuring, she ended up a Director in record time. Armed to the teeth, she set out on her own, and now focused on consulting across all industries, she hasn’t looked back since.

Lena is an outdoor girl through and through, if she’s not fishing, camping, or hiking, she’s working on perfecting her garden. Now residing in Connecticut, she is a Master Gardener and volunteers her time to promote sustainability, food justice, and healthy eating. We got dibs on her when the apocalypse hits. 

You survived a pretty rocky road working at a marketing software company, but left with a Director title, can you tell us a little about that journey?

When I started my career in software marketing I was naive to the nature of the industry: hiring young people, giving them ‘perks’ like a room filled with bean bag chairs, and work them as hard as possible until they quit. Like many tech companies, we were acquired and restructured which lead to a lot of people being suddenly laid off: including my boss and the rest of my team.

Although any sense of job security was gone, I also saw opportunity to take on roles I had wanted as a leader in the marketing department. I proposed my position, strategy, and team structure and was promoted to Director of Demand Generation. Although it was trying - in retrospect it would be hard to have gotten that experience, met my talented coworkers (many of whom have become clients), and gained the confidence to shape a career that I wanted.

What made you go out on your own and start consulting?

I started consulting right out of college out of necessity of a bleak job market. I was qualified but didn't have the required “2-3 years of experience” that come with “entry level” positions. So, I started taking on extra consulting to quickly gain additional years of experience. I've continued consulting through my career and once I knew I didn't have the job security traditionally associated with working a 9-5 becoming a consultant seemed less daunting. Once I had lined up enough projects to see me through the first 6 months I felt comfortable to quit my day job.

Do you have any day-to-day rituals to add structure to your days?

To be honest, not really and I kind of love that. I do enjoy taking time in the morning to make a pourover coffee and reading the news as I prepare for the day. I never had time in the mornings when I worked 9-5 because my commute was an hour each way. The most immediate change for me was having more time to myself and less alone in the car.

Is it difficult not being in an office setting with coworkers, working from home?

I have consultant coworkers who I chat with frequently, and in-person client meetings so that aspect hasn't changed much. My husband, Josh (*who full disclosure works at Rubric) also works from home so I still get to have daily human interaction. Beyond that, jobs that were traditionally in office are suddenly now offering remote positions so I do feel like this is a fundamental shift in the way that people work. From early pandemic zoom/video heavy meetings to now missing a traditional conference call - we are collectively working out the kinks.

Who do you turn to for advice on hard to tackle projects?

I have a few mentors in marketing who I sometimes come to with big decisions or projects. Having someone who has been in the industry and whose advice you know is catered to your success is invaluable. Be careful who you take advice from and their underlying motivations. My mentors are mostly former bosses but I also turn to my friends, peers, and other consultants if I have questions specific to their expertise/industry.

How were your first few years on your own?

My first few years have been great! Not only have I made enough money to support myself and grow my business but more importantly I have time to do other things that I'm passionate about. I became a Master Gardener, where much of my time was devoted to community service in Baltimore. From there, my husband and I moved to LA just in time for lockdown and subsequently moved to the woods of Connecticut. Already having a job that doesn't require going to an office was a blessing once the pandemic hit.

What are some things you learned after becoming your own Boss?

Take time to understand how taxes work, talk to other consultants, and get a good accountant you can trust. Spending time and money upfront to figure all this out can save you from surprises in the tax season. Look into forming an LLC to protect your personal assets should something happen. Oh, and its important to have an online identity so make sure you have a website that speaks to your expertise and personal brand. It is crucial to have a quick link that you and your contacts can share for networking and new business.

If you or someone you know is a BOSS, let’s chat.