Embarking on a career journey often involves unexpected turns and pivotal moments that can redefine seventeen’s professional trajectory. From CEOs to Brand Managers, we’ve gathered 17 unique stories that span the spectrum of career evolution. Discover the transformative tales like an unexpected leadership role in Madrid to the life lessons of a time management consultant & keynote speaker that have significantly shaped these professionals’ paths.

• Unexpected Leadership Role in Madrid
• From Sales to Marketing Alignment
• Unconventional Path to Brand Management
• Transformative Leadership through Education
• Banking Analyst to Legal Funding
• Designer to Children’s Fashion Entrepreneur
• Marketing Shift from B2C to B2B
• Chance Meeting Leads to Startup Success
• Army to HR Transition
• Engaging Webinar Inspires Career Opportunity
• Negotiation Skills Spark Law Career
• Diverse Experiences in Marketing and Advocacy
• Electrical Technician to Sales Account Manager
• Travel Inspires Shift to Real Estate
• Banking to Startup Consultant Evolution
• Life-Altering Surgery Teaches Work-Life Balance
• Entrepreneurial Journey from Newspapers to Consulting

Unexpected Leadership Role in Madrid

At the beginning of my career, after learning Spanish within a few months and relocating to Madrid, just ten months later, I found myself in a leadership role at The Boston Consulting Group (BCG), despite having no formal leadership background or prior experience. Interviewing along with two external candidates who were native Spanish speakers with relevant experience, my potential was recognized, and I was given the opportunity.

My proactive suggestions for improving local structures and processes, unwavering commitment to my teams, and flexibility in facing challenges were key factors in my selection. The external recruiters that were hired to coordinate the interviews also had us go through some psychological tests, the results of which I am unfamiliar with. This experience shaped my approach to hiring, emphasizing the importance of recognizing potential in others, with attitude being a key factor as well.

Taking on this role felt like jumping into cold water, but I quickly adapted and grew into my new responsibilities. Later, BCG opened an office in Lisbon, in which I had a very active role, and I soon managed two offices: the existing one in Spain and a new one in Lisbon, Portugal. This journey underscores the transformative power of taking risks and embracing opportunities.

Regina Huber, CEO & Founder, Transform Your Performance

From Sales to Marketing Alignment

I started my career in B2B sales and thought that’s where I’d be forever. But after not getting a promotion I absolutely thought I deserved, my boss asked me to consider a move to marketing. It was a huge risk, but I had recently taken the StrengthsFinder test and realized that the new role played to my true strengths in a way that sales didn’t. 

So I took the leap, and it transformed my career trajectory, leading me down a path that was a lot better aligned with my skills, goals, and true purpose.

Kasey Jones, Founder and CEO, A Better Jones

Unconventional Path to Brand Management

My journey to brand management wasn’t the standard straight path that many others have taken. The normal route to brand management, straight after university, involves getting onto a graduate scheme where one of your rotations will be brand management (if it’s a general scheme). However, these are extremely competitive to get onto, where candidates will often already have extensive summer work experience, at least a 2:1 grade at university, and would be competing in multiple interviews, which this summer work experience helps to support. 

Knowing I didn’t have these resources or experience, I decided to join a start-up of 15 people that ran facilitation events for healthcare organizations straight out of university. It was a brilliant first step into my brand management journey as I was given projects that I had complete autonomy over as a 23-year-old, which is very unique to be able to do at my age, and allowed me to build the basics on scoping out a project and hitting key KPIs. With this valuable and relevant working experience, I applied and was accepted onto the Heineken Leadership scheme, where I was able to get brand management training and an incredible network.

Getting onto this graduate scheme ultimately has helped me get every brand management job since, both in the UK and abroad, so aim to get onto these schemes so you can set yourself up for success in this career!

Natalie Skinner, Brand Manager, Vega

Transformative Leadership through Education

The First 10 Years: Spent time in food service and retail roles, moving from associate to management. Went to college at 18. Quit college at 20. Met and married my ex. Moved across the country to upstate New York. Transferred my job and subsequently got laid off not long after. 

Pivot #1: To cover the bills, I went back to retail and started working under a leader who completely changed the trajectory of my life. Noel was in her mid-50s at the time. Spunky and driven, one day she announced that she was going back to school. She encouraged me to go back and finish my degree, and so I started back on that path.

The Next 10 Years: Earned my bachelor’s degree. Got divorced. Returned to Minneapolis. Earned my master’s degree.

In March 2008, I took the role of HR Manager for a locally-owned food co-op in the south metro of Minneapolis with about 100 staff. Wore all the HR hats for 12 years. Learned what I loved (and what I could do without).

Pivot #2: In 2019, everything changed again. I was selected to train under Brené Brown and become a Dare to Lead Certified Facilitator. In that moment, life put me on a path that I remain on today: leadership and professional development.

In January 2020, I transitioned into a Learning and Development Manager role for a manufacturing organization – 20+ locations, 5,000+ staff, and an integrated supply chain – and built their L&D department from the ground up as a solo practitioner.

In June of 2022, I decided to evolve my career journey again and took a role as Sr. Manager, Global Leadership and Professional Development Projects for a government contractor. With this role, I oversee the work of the Shared Learning Model – a collaborative, cross-functional, inter-departmental initiative bringing Learning and Development leaders from six global locations together – representing 39,000+ employees – to work on learning initiatives that have been vetted and approved within the strategic business objectives.

How did I get here? Some days, I still have no idea, but if I had to put language around it, it would boil down to this: A fierce belief in myself, some courageous leaps of faith into the unknown, and God’s grace.

Here’s to believing that anything is possible, and leaving room for the seemingly impossible to become reality!

Paula Grace, Sr. Manager, Global Leadership and Professional Development Projects, Maximus

Banking Analyst to Legal Funding

Starting my career in investment banking was a thrilling experience. I joined Morgan Stanley as an Investment Banking Analyst right after graduating from UC Berkeley with a degree in Economics. The fast-paced environment and high-stakes deals taught me much about finance and business strategy. Despite the demanding nature of the job, the skills and insights I gained were invaluable. During this time, I discovered my passion for problem-solving and helping clients navigate complex financial situations.

After a year and a half at Morgan Stanley, I decided to make a significant shift. In 2017, I became the Managing Member of Uplift Legal Funding. Moving from a traditional finance role to the legal funding sector was a bold step. This decision was driven by my desire to make a tangible difference in people’s lives. At Uplift Legal Funding, we support individuals involved in lawsuits, helping them manage their expenses while they await settlements.

One of the most impactful moments in my career was seeing the direct positive impact of our services on clients’ lives. Knowing that our financial support helps people get through tough times is incredibly fulfilling. My journey from investment banking to legal funding taught me the importance of adaptability and following your passion.

Jared Stern, Managing Member, Uplift Legal Funding

Designer to Children’s Fashion Entrepreneur

Once upon a time, my career journey took an unexpected turn. Starting as a designer, I soon realized my passion for creating unique and innovative pieces that captured the imagination of both kids and parents. Embracing this vision, I ventured into the world of entrepreneurship, founding a children’s clothing and accessories brand that stood out for its creativity and quality.

One turning point that shaped my path was when I decided to focus on sustainable and eco-friendly materials, aligning my business with values that resonated with modern families. This decision not only set us apart in the market but also fueled our growth as conscious consumers embraced our brand.

Through dedication, hard work, and a touch of creativity, my unusual career journey led me to a place where I could make a difference in the world of children’s fashion. As we continue to grow and innovate, I am reminded that sometimes the most unconventional paths lead to the most fulfilling destinations.

Nikhil Soni, Founder, The Tribe Kids

Marketing Shift from B2C to B2B

During the pandemic, I was working as a Marketing Coordinator for a footwear and apparel brand. It was a crazy time, filled with uncertainty and new challenges. Shortly after starting my new role there, a friend referred me to a startup called The Owl Solutions, suggesting I do some freelance work for them. Little did I know, this would change my career path.

Shifting from B2C to B2B marketing felt like stepping into a whole new world. Working at The Owl Solutions, a small but ambitious startup, I was thrown into a whirlwind of learning and growth. It was intense, but incredibly rewarding.

One of the best parts was having access to amazing mentors. These were people who had been through it all and were more than willing to teach me everything they knew.

At The Owl Solutions, I also had the freedom to experiment. I could test new ideas, iterate quickly, and find what truly worked. This kind of hands-on experience was something I’d never had before, and it was exhilarating.

What really stood out, though, was getting to see the bigger picture. In a startup, you aren’t just confined to your role; you get to dip your toes into different aspects of the business. This holistic view was eye-opening and gave me a deeper understanding of how everything fits together.

Looking back, my journey from a Marketing Coordinator at a well-established brand to a versatile marketer at a dynamic startup is filled with unique experiences and pivotal moments. Each step taught me something new, shaping me into the marketer I am today. It’s been an unpredictable ride, but one that I’m incredibly grateful for.

Olivia Santucci, Senior Marketing Manager, The Owl Solutions

Chance Meeting Leads to Startup Success

This is a situation where I was working for a small company while also contributing to a user group of software that we were implementing in our organization. I was the administrator for this software, so I had a lot to contribute to the user group’s questions. Someone noticed and reached out. We got to talking, and after a few months of chatting and getting to know each other, I was asked to accompany him to a meeting. On the way, he said he needed to stop by for a little while at another company. We stopped by and I was introduced to the CTO of that company. The CTO started talking about what they were doing, what my experience was, what technology I had experience with, and so on. We chatted for about an hour and left for our next meeting.

Once we were in the car, I was asked if I liked the talk with the CTO. I said I enjoyed it very much and was fascinated by what they were doing. ‘Well, they would like to offer you a job if you want it. That was your interview!’ I was flabbergasted. I decided to take the plunge and joined that startup as employee number one! The company went on to grow, and we went public with a market cap of over $1 billion. This was a huge turning point in my journey. 

I always say, you don’t know who will come to help out when. Be a good human and speak with everyone nicely. Always think about how you can help others in whatever shape or form. Your kind words may be all that is needed at that time. 

That interaction led to a great career with that company but also opened up new doors for me. I have had a stellar career and varied experiences and am grateful for that opportunity. I have gained insights into operating at levels I had never dreamed of and have learned so much!

Shishir Khedkar, Head of Engineering

Army to HR Transition

I spent six years in the Army and then climbed telephone poles for a living. Now I’m an HR professional. While there were many aspects of my previous job that I loved, I knew I didn’t want to do it forever. I also didn’t know what else I wanted to do.

One evening, I sat down and listed what I loved and hated about each job. I then started taking college courses to finish my degree and began networking with professionals to explore potential career paths. It was a combination of doing all those things that led me to the field of HR, and I absolutely love it.

I remember being interviewed by a corporate executive who asked me to explain why my resume seemed so ‘zigzaggy.’ I laughed while I thanked them for asking that question. I recognize my path is not linear and might not even make sense. However, each experience has added significant value to my current role and has shaped me into the professional I am today.

Scott Johnson, HR Manager

Engaging Webinar Inspires Career Opportunity

I watched a live webinar where the founder of the company, Beth, was giving a talk on email marketing. She was incredibly engaging, and I sent her a message on LinkedIn to tell her so! I then followed her company, and when there was a job opening, I snapped up the chance to apply. And here I am today!

Chloe Birch, Marketing Manager, Astral Digital

Negotiation Skills Spark Law Career

In roughly 2011, I was working as an inside-sales agent at an insurance company. I got involved in a negotiation regarding a change to the compensation policy that arguably resulted in significant unpaid commissions to a group of inside-sales agents (including me). We successfully resolved the issue. Afterward, my manager suggested that I apply to law school. He did not promise anything but indicated there was a possibility that the company might be open to paying the tuition and moving me to the legal department.

I took the LSAT and applied to a night law school. I was offered a substantial scholarship by the law school. By then, PPACA (the Affordable Care Act) had resulted in substantial changes to the insurance company, and particularly to my department, which ultimately disbanded. I just went ahead and started law school anyway and obtained employment clerking for a local workers’ compensation law firm. I now run a legal practice doing workers’ compensation litigation.

That one conversation with my manager completely changed the trajectory of my career, in a good way, but not even close to the way that I had planned.

Luke Smith, Attorney and Founder, LawSmith PLLC

Diverse Experiences in Marketing and Advocacy

From the moment I stepped into my first professional role as an AmeriCorps member at an environmental justice clinic, it was clear that my ability to connect with diverse audiences would be a driving force in my career. As the sole communications representative, I took charge of end-to-end campaign planning, execution, and optimization, working with individuals from all walks of life—Somalian refugees, Hispanic migrants, blue-collar workers, and affluent donors alike.

When my AmeriCorps year was complete, I launched a marketing consultancy in the Portland Metro area. One of my biggest accomplishments was advising one food cart which has since flourished into a global sensation with ten brick-and-mortar locations.

While the consultancy was a valuable learning experience, I missed working with a team. I joined a startup company empowering journalists to succeed in the digital world. Working alongside seasoned professionals like Emily Harris, formerly NPR’s Central & Eastern European Correspondent, I honed my skills in crafting thought-provoking forum questions and managing intricate cross-departmental logistics.

My next role was at a government-run patient safety advocacy organization, where involvement with their Task Force presented a unique opportunity to engage with patients, families, and providers as they shared their personal stories and perspectives. By learning to acknowledge and honor these diverse viewpoints, I mastered the art of creating an inclusive environment where everyone felt heard and valued.

In 2017, I was approached by a venture capitalist I previously met at a networking event regarding a marketing role at a brand-new VC fund focusing on investing in companies that created “Delightful Moments.” While I wasn’t an investment expert, I was eager to embrace the challenge and built our entire internal and external communications infrastructure from scratch. During my seven years, the fund has rapidly grown and expanded internationally, and I’ve advanced to VP of Marketing and Internal Communications.

Nicole Staudinger, Director of Marketing, Joyance Partners

Electrical Technician to Sales Account Manager

My professional path has taken turns that I never would have thought possible. I graduated as an electrical technician, but the only jobs I found in my early career were as a metalworker. I’ve done this type of job for years, but I felt dissatisfied and unmotivated. There was something blocking my personal development: my mindset. 

After reading the book ‘Secrets of a Millionaire Mind,’ I realized that I needed to make a change in my life. The goal was to find work where I could work based on targets, not hours. I started studying psychology and sales and focused on my personal growth. In March 2017, a company contacted me for a junior sales account position, but I was rejected because another candidate had experience in this field. I felt devastated, but I knew I couldn’t give up on finding a job I really liked.

In July 2017, the same company contacted me again; an employee had quit, and they wanted to hire me. I worked hard for years, trying to learn everything from my older colleagues and my manager. It’s 2024, I am an account manager and manage seven other people. Even today, I have a lot to learn, and I try to be as humble as possible. My friends tell me that I was lucky, but only I know what I went through and what I did to achieve all this.

I learned you must always follow your dreams, no matter what happens or how hard it is.

Giovanni della Ventura, Head of Content, giodella.com

Travel Inspires Shift to Real Estate

My unusual career journey went from aspiring physiotherapist to real estate investor. In 2019, I had planned to go to physiotherapy school, and I was doing entrance exams to be able to get in. Something in my heart told me that this wasn’t going to be the exact path for me, so I ended up traveling abroad in 2019 and, of course, did not pass the exams.

During this experience of traveling abroad, I came across lots of different real estate investors and people who were involved in real estate. This opened my eyes to the possibilities of shifting away from physiotherapy and doing something that had much more scale. I started to take various real estate trainings and became more passionate about it. Covid hit, and the physiotherapy licensing exams were canceled, so even my friends who got accepted into physiotherapy school could not complete their final exams to become licensed practitioners. This was the moment that showed me that I had made the right decision by listening to my heart and changing the direction of my career.

During 2020 and onward, my real estate career started to advance; I began training other people, and we began to seriously scale our real estate investing company. I really started to see that I was in the right place, even though so many people had wanted me to become a physiotherapist in the past. I’m grateful for the unfolding of various events in my life that led me to these moments.

Sebastian Jania, CEO, Ontario Property Buyers

Banking to Startup Consultant Evolution

I guess you could say my career journey is anything but ordinary. It all started with a banking apprenticeship. I thought I’d be crunching numbers forever, stuck in a world of ledgers and financial statements. But then, the universe threw me a curveball. I got the opportunity to join N26, a burgeoning fintech company, where I got my first taste of the startup life. The chaos, innovation, and constant caffeine buzz hooked me instantly. I was like a kid in a candy store, diving headfirst into the whirlwind of digital banking.

After my stint at N26, I joined Civey, a market research firm in Germany. I was knee-deep in business models and marketing campaigns, and there was more data than you could shake a stick at. One particular project had me analyzing consumer behavior patterns, which was fascinating and a little overwhelming. It was during this time that I realized how much I loved the dynamic nature of market research and the insights it could unlock.

Next up was Deutsche Bahn, where I worked on international expansion and business strategy. This role felt like being a detective, piecing together market trends and competitor strategies to drive growth. Ever tried making sense of the global transport markets? It’s a wild ride, let me tell you.

But the real turning point came when I joined the BMW Startup Garage. Leading over 30 venture-clienting projects was like being part of an automotive innovation pit crew. There were countless late nights and lots of coffee, but the “aha” moments made it all worthwhile. Helping startups refine their business models and secure deals with a giant like BMW was exhilarating.

Finally, I landed at Spectup. Here, I lead a team of startup experts, helping young companies grow and attract investors. The most satisfying part? Seeing a struggling startup turn into an investor magnet and growth powerhouse. It’s like watching a plant you’ve nurtured finally bloom.

So, from banking to fintech, market research, global strategy, and venture clienting, my career has been a series of unexpected twists and turns. Each role taught me something new, and each experience shaped the consultant I am today. It’s been a wild ride, but I wouldn’t trade it for anything.

Niclas Schlopsna, Managing Consultant and CEO, spectup

Life-Altering Surgery Teaches Work-Life Balance

I didn’t become a balanced business owner until I almost died. After years of living as a high-functioning but very burnt-out workaholic, I had a surgery that changed my life. It made me realize work-life balance is an essential part of career success and changed the trajectory of my life. Not only did this turning point change the way I was working, but it also changed my work as I am now a time management expert teaching others how to be more productive while being even more present in their lives.

Samantha Lane, Time Management Consultant & Keynote Speaker, Origami Day

Entrepreneurial Journey from Newspapers to Consulting

I was always entrepreneurial but still struggled with the ‘practicality’ of having a 9-5 for many years. I’ve done everything from delivering newspapers (what’s a newspaper, you ask?) to bussing tables, to delivering milk, to selling guitars to celebrities, to bringing a dead NYC company back to life, to building and selling my own online businesses, to marketing consulting.

The last J-O-B I had was in 2013, where I wanted to go back on my own and do my thing. I had a great relationship with the owners, so instead of quitting cold, I tried to convert them into a retainer client. After corralling them like sheep into a meeting room and pitching them my offering (free up a desk, no benefits, flat-fee pay structure, and definable deliverables), I thought I had them. Unfortunately, they were so old-school they simply couldn’t fathom me not being at the office every day. So, I just quit cold and went on my own.

I ended up building a small local marketing agency in NYC, which I later sold. I then built an e-commerce brand from scratch and later sold it to a competitor after growing that to over $728K in revenue with only SEO. In the middle of all this (and for much of my life) was a lot of pain, suffering, isolation, food stamps, and running 5Ks (with a backpack on) to and from the library to ‘go to the office,’ which was really just me sitting next to homeless people who didn’t smell too great.

All in all, I wouldn’t have traded my experiences for the typical ‘safe path’ that society recommends everyone take. Though, I would say that MOST people should stay the normal path because it takes a super-metric-ton of perseverance, mental fortitude, and relentlessly believing in yourself to make things happen outside of the system.

For those that have that entrepreneurial spirit and that burning flame inside them to make it happen, then I always say to DO IT.

For those that are scratching at the wallpaper of entrepreneurship but too nervous to jump in headfirst, keep your day job and build something at night (or at your job if you can get away with it). Then transition out when your ‘thing’ can supplant your day job income. Or do what I did and try to convert your employer into a client.

It really comes down to the individual. How they think, what they want, and how they are built is what dictates if they should play it safe, do the ‘upshift/downshift’ method mentioned above, or take the plunge into the abyss.

Mike Bonadio, Owner, Mike Bonadio Consulting