Hustle + Flow: The Career Remix

My business is people. Technology allows me to be more creative in helping those people and organizations do the things they want to do.

These words, born from breakdancing on cardboard in downtown Halifax in the 80s, have become the unexpected foundation of my business philosophy. From collecting cans to working at the flea market on Sundays, I couldn't have imagined how those early hustles would shape my approach to entrepreneurship decades later.

I recently shared part of my story on Carrie Forbes' podcast, "The Disruptive Jam," exploring how my path from libraries to founding 20/20 Digital reflects both hustle (putting in the work) and flow (finding your authentic path).

Today, I want to share some key lessons from that conversation that might help others navigate their non-linear careers.

The Bucket List Approach to Career Building

My journey hasn't been a straight line. From public library clerk to founding 20/20 Digital, I've zigzagged through different sectors, roles, and challenges.

At 26, I landed a senior position at the library that most people hold until retirement. It would have been the "safe" path—the traditional career ladder we're often told to climb.

But I've never viewed my career as a ladder. Instead, I see it as a bucket list of experiences.

While working in the library system, I returned to school for web programming, preparing myself for a potential shift. When I finally got an offer from a newly started agency, I hesitated to take the leap. Even with preparation, moving from the security of the public sector to the uncertainty of a small startup agency wasn't easy. Eventually, I bet on myself and took that chance, joining a company with just four people working almost out of a garage, gambling on potential over security.

Each transition might have looked disconnected from the outside, but they all contributed to a collection of skills that enabled me to launch my own business.

The traditional career advice says specialization is key, but my non-linear path gave me a unique perspective I couldn't have developed otherwise.

The Hip-Hop Mindset in Business

“No rapper can rap quite like I can.” — LL Cool J, “I’m Bad”

Just as my career has followed an unconventional path, my business philosophy draws from equally unexpected sources. I still remember breakdancing on cardboard in downtown Halifax. LL Cool J's "I'm Bad" wasn't just the first rap song that greatly impacted me—it changed how I saw myself. Something about his confidence, his self-belief, showed me what was possible.

What drew me to hip-hop wasn't just the music; it was the storytelling. These were experiences I could relate to, from people who created something meaningful despite limited resources.

I bring this same thinking to my business today. When I look at problems, I'm not stuck on doing things traditionally. I focus on what will help the people I work with, not just what's most profitable. I look for fresh solutions and stay open to trying approaches that others might overlook.

Like in hip-hop, sometimes the best results come from remixing what already exists into something better.

People Before Process, Process Before Product

If there's one philosophy that defines my approach to business, it's this: people first, then process, then product and service.

In my UX work, there's nothing more eye-opening than watching people use a product or service. As I often share in my presentations, "It's not about how we think they use it. It's about how they actually use it." That gap between what we imagine and what really happens is where all the critical insights live.

Businesses achieve the most successful transformations when they begin by asking questions instead of jumping to solutions. To see the whole picture, you need insights from different sources—staff interviews, client feedback, analytics, and direct observations are just a few examples. A 360-degree understanding allows you to align UX improvements with your organization's needs and tackle root causes instead of merely treating symptoms.

One size does not fit all. What works for one organization might not work for another, even in the same industry. The key is to build a strong foundation by understanding your users and your business's specific context.

I love working with organizations that get this. They're not just looking for someone to execute their plan. They want to bring different departments together, challenge their assumptions, and try new approaches while staying true to who they are as a business.

Technology as a Tool for Human Connection

I still remember being in college and having to sign up to use the single scanner we had in the lab. Fast-forward to now, and I watch my 14-year-old son with multiple devices, gaming on his computer while keeping a group chat on his iPad, coordinating with friends to meet up in VR on Saturday night.

What interests me isn't just where technology is today but where it's going and how we adapt alongside it. Even with the rapid rise of AI and other emerging tools, I keep it simple: My business isn't technology. My business is people, and technology helps me serve them better.

No matter how much things change, we're still in the business of people. That's what matters most.

Betting on Yourself

Throughout my career, the one constant has been betting on myself.

When I was 26, I applied for the most senior role I could get with my education at the library. There was only one of these roles per branch, and people usually kept them until retirement. Getting this job over peers with more experience caused a bit of disruption in the system.

But I earned it by doing things differently:

• I took shifts at branches nobody wanted
• I learned systems that others didn't bother with
• I created programs nobody asked for

I didn't wait for permission. I just went for it.

My journey started even earlier, though. When a new community center opened in my neighbourhood, I walked in and offered to volunteer. I knew the local kids needed something positive to do. That volunteer gig led to my library job, an opportunity I never initially saw coming.

These weren't reckless gambles. They were calculated risks based on knowing what I was capable of and being willing to back myself when others might have played it safe.

Mentorship as a Two-Way Street

I've had many mentors over the years, but early on, three people stood out:

The first mentor helped guide and coach me to return to school, which opened doors I hadn't even known existed.

The second was someone closer to the end of my public service career who was very good at guiding me and giving me more context around scenarios—not just looking and hearing, but listening and reading between the lines.

The third was someone I reached out to through an organization when I was transitioning from programming to focusing on user experience work. They were willing to give me time to answer questions and help me work through specific scenarios.

I enjoyed the experience of having a mentor, so much so that a big theme throughout my career has been providing and giving back to the community.

If you're looking for a mentor, here's what worked for me:

• Find someone doing the things you're interested in
• Be willing to be coached, not just advised
• Take the initiative to reach out—don't wait for someone to find you
• Apply what you learn, then follow up to share the results

On the flip side, when I became more seasoned in my career, I found huge value in sharing back with the next generation. Here's my approach to mentoring:

• Give time through formal programs and informal coffee chats
• Build relationships that carry throughout the years, some on a semi-professional basis and others more informally
• Help provide perspective on things they might not otherwise have thought about
• Connect them with other people in your network who can help with specific challenges

Mentorship has been critical for me from a learning and growth standpoint, but it also gives me perspective. The best way to learn about something is to talk to somebody doing it.

Yearly Recap and Evolution

A fundamental practice that keeps me aligned with my values and goals is my year-end review process. At the end of every physical business year, I assess what worked well, what didn't, what was profitable, what wasn't, what I enjoyed most, and what I enjoyed least.

This reflection isn't just about numbers. It's about constantly evaluating whether I'm still building the experiences I want on my career bucket list. It ensures that my business evolves as technology, markets, and my interests do.

The name 20/20 Digital comes from this philosophy: the clarity of hindsight and a clear path forward. It's about learning from the past while remaining flexible enough to adapt to the future.

For Those Thinking About Non-Linear Careers

For me, it's looking for ways to experiment and hedge some safe bets initially, especially if you're just starting.

I do not recommend quitting your job and then going to do the thing that you're aspiring to do. First, look to see if there is a market for what you're interested in, then find people who are doing what you want to do and learn from them.

If you're considering a non-linear career path or entrepreneurship, here's my practical advice:

• Test before you leap: Start side projects while still employed to validate your ideas.
• Build transferable skills: Focus on building skills that go beyond specific industries, such as communication, problem-solving, and relationship-building.
• Collect experiences, not just credentials: Say yes to projects that stretch you, even if they don't fit neatly on your resume.
• Leverage your unique background: Your "unrelated" experiences are often your greatest differentiators.
• Make reflection a habit: Regularly assess what's working, what isn't, and where you want to go next.

My 14-year-old son wants to be a YouTube content creator. He is taking the time to understand the analytics, viewership, how to cut a video, and even what the thumbnail should look like. He's educating me on how the analytics work and how he gets traction. So he's spending a lot of time learning about the craft and the business side, not just the creative piece, and then applying those things he's learning.

The Rhythm of Success

I don't talk about money or hitting targets when people ask me about success. For me, it's much simpler—do I enjoy my work? Am I making a difference for my clients? Are they better off after working with me? That's how I measure whether I'm on the right track.

I see running my business a lot like hip-hop. It's partly about the hustle—showing up every day, putting in the work, and creating opportunities where none existed before. But it's also about the flow—finding that sweet spot where the work feels natural, where my skills and clients' needs align perfectly.

My life's soundtrack has changed since those early days of breakdancing, but the principles haven't. I'm still applying that resourceful mindset with different tools and a broader canvas, telling stories that matter. And even though I'm running a digital agency instead of practicing moves on cardboard, I still find my rhythm every day. ✌️

Want to hear more about my journey and the intersection of hip-hop culture and business philosophy?

Watch or listen to my conversation with Carrie Forbes on "The Disruptive Jam" podcast on YouTube, exploring career transitions, mentorship, and finding your authentic professional path.

I'm Jamie Gerrard, founder of 20/20 Digital. We help organizations navigate digital transformation with a people-first approach, creating product and service experiences that drive measurable business results while truly resonating with both customers and employees.

Let's connect if you're ready to transform with purpose and clarity.

LinkedIn: Jamie Gerrard | 20/20 Digital