Can you reverse-engineer your success by connecting the dots from your current position to the steps you should have taken to end up there?

The answer for me is “No”.

I never imagined myself becoming the CMO of the fastest-growing and most innovative women’s health company in the US.

Just 5 years ago, I quit my job as the CEO of the leading digital agency in Eastern Europe and moved to San Francisco, barely speaking English.

Now, I’m sitting in a stylish and bright community coworking space, looking over the San Francisco Skyline, and listening to my university role model Guy Kawasaki answer the same questions at his new book presentation.

“Would I have guessed that a Japanese immigrant's kid living in Hawaii would eventually work as Apple's Chief Evangelist? Absolutely no,” he repeats.

Similarly, I believe, I was fortunate to be in the right place, with the right people, at the right time.

Despite being such an obvious and entry-level recommendation from any career development article, taking risks is more mentally challenging than anything else. It feels like you put everything on the line and may lose years of previously invested time and money.

Hearing stories of other people taking the courage to start from scratch has helped me to deal with the anxiety of ambiguity. You can’t guarantee or predict success, but reflection helped me minimize a negative outcome. Today, I want to share some of these with the Elpha community.

Zoom Out when you feel stuck

When I lived in Belarus, I was very meticulous in building my career in advertising. I got a bachelor's degree in PR and an MS in cultural studies from European Humanitarian University, participated in the Young Cannes Lions PR competition, and intentionally worked with recognizable Fortune 500 brands.

Every opportunity that emerged during these 10 years was measured by how it could take me or my agency to the next level. At some point, I felt I had reached the pinnacle. Great role, big team, festivals, fancy presentations, and interviews for magazines. This is when I started to think globally, questioning what I was doing, what impact I was making, and who I could learn from.

I realized that my definition of success in my career was shaped by the specific context in which I operated. For example, our clients' advertising budgets were not large enough to support high-scale campaigns, so we had to adapt global strategies to suit their scale. We also had to adhere to local censorship laws which required us to strictly edit fun and creative ideas.

Learning in this way gave me the courage and “appetite” to shift to another context and start again, changing my perspective from taking the risk of losing something to reducing the risk of not taking an opportunity to play bigger.

Create room for opportunities to happen

Growing up, I was taught a fairy tale about a frog that got trapped in a milk jug and chaotically moved around trying to escape. The frog’s movement in the milk turned it into butter, and the frog successfully escaped.

Similarly, I discovered that, in many situations, doing something was more helpful than doing nothing.

When I moved to San Francisco, I spent my first month reaching out on LinkedIn to CEOs of all Bay Area digital and advertising agencies, going to design and marketing events, and attending job fairs.

My first gig I got from LinkedIn outreach, a head of strategy invited me to their agency office. My English was very poor and I noticed that he barely understood my pitch. Seeing how I was losing his interest, I offered to intern for them for free. I had an incredible portfolio and I knew I could prove myself in my work.

A couple of months in, I was pitching an SEO strategy on a call with a client, to a large financial institution. I thought I wanted to work in the agency business, but by developing digital transformation programs for banks and credit unions I became interested in FinTech and decided to look for better-paid opportunities in a startup.

At a job fair, I met a classmate and he introduced me to his company's product marketing team. After a brief chat, they offered me a paid internship. I didn’t know anything about b2b marketing and their industry, but decided to take it. I feel that the magic sense of “luck” is overestimated. If you put yourself in a high-nurturing context and surround yourself with inspiring people, you will catch a wave even without knowing how.

Leverage your experience

I often get asked how difficult it was to learn marketing in another country and if any of the skills I had before were useful. This question is upsetting in a number of ways. It not only minimizes the impact of your experience but also assumes that professional skills are not transferable hard skills. I know from interviewing, hiring, and developing more than 50 managers in my career that sometimes soft competencies and motivation are more important than understanding software tools.

After working with fintech SaaS, I missed consumer-facing marketing and I wanted to work at a startup with a mission focused on sustainability, social impact, or healthcare.

I applied to many companies, from lab-grown diamonds to mental health gyms. In every cover letter, I tried to link my past clients or experience as a throughline to working in a completely different country and language.

Eventually, I found a marketing contractor role at my current company on Indeed. An agency I was running had the biggest period tracker app as a client. We did animation content for them and advertising assets. I mentioned this in my cover letter and got an immediate call from the founder. She invited me to an interview that I decided to treat as a pitch to a new client. I prepared a deck with ideas on how to improve their basic marketing strategy using Canva and writing the advertising copy myself. I got the job.

I was only the third hire after founders, so I wore many hats: social media, customer support, emails, design, copy, ads, partnerships, and calls. I was exhausted, but I decided to embrace it and challenge myself to do a job that I previously managed, in a language not native to me, in a country I had only recently started to call my home. When the pandemic hit, we started to grow a lot and I got back on the management track, hiring people, and agencies, and doing what I enjoy the most - coaching, analyzing, and project management. My previous experience was nothing like this. I've never used as much AI and marketing automation software and sophisticated data tools, so layering it on top of basic marketing knowledge, management, and communication helps to learn it very fast.

Whether it’s moving to another country, taking on a new role, a new industry, or giving up your stable and predictable career for a new opportunity, making any change is scary. Most likely, it will be tough on your ego too. Starting something from scratch, and stepping down to become a beginner again. However, framing it as a learning experience can help a lot. Consider this adventure as an educational program, where you can collect credits from new subjects to get a higher grade and move forward. Evaluating your risks from a big-picture mindset, continuing to pursue something even when you are not sure if it is the right path, and building on top of your previous achievements increases chances for success.

If this topic resonates with you, share your story. Have you ever put everything on hold and made a risky decision? What helped you to take the courage to do it? What would you recommend to yourself from connecting all the dots now?