Following My Curiosity: My Journey from Blogging to Entrepreneurship
How I went from blogging as a side hustle to becoming an entrepreneur
Hello and Welcome!
If you’re new here, drop me a line to say hello. This week, I’m taking time to share more of my own journey to entrepreneurship
One of the questions that I get a lot is “How did you leave corporate to become an entrepreneur?” I wanted to take some time to write down my journey and am sharing it in this week’s newsletter.
How It Started: A Curious Itch
I started off my side-hustle and side businesses when I was in business school. I started my blog, MBASchooled to write about my MBA experience and how it was helping me build a career. Truthfully, I had a lot of free time during my second year of business school, and I wanted to use some of it to do something I found interesting.
Around that same time, I also began career coaching, first, through being a graduate assistant at my business school, and then eventually through getting asked to join a leadership and career coaching platform.
Both of these activities allowed me to use my strengths to help others, but they also gave me a lot of excitement and energy. I loved creating when I wrote and blogged, and I loved the ability to guide and coach people and help bring out the best in them to find the next step in their career.
I loved my side jobs, but graduation meant it was time to enter the 9–5 world as a management consultant. It was a good job, but I didn’t find it amazing. But having two things to do outside of my day job gave me energy and a chance to funnel my curiosity and creativity.
After writing for about a year, the blog started to get some traction amongst the top MBA programs. In 2016, I accepted an invitation from an MBA program to give a talk. A rep from the school asked what my speaker fee was. Suddenly, I was a paid speaker! I was hooked on the idea. Through speaking, I could share knowledge, tell stories and inspire audiences.
Leaving Consulting For Product Marketing
I always knew I wasn’t going to be a consultant forever, and after 2.5 years of doing it post-business school and 7 years total I was ready for a change. Because I was writing, coaching, and speaking so much outside of work, I began to think about how I could integrate these more into my next job.
After going on my own career exploration, I found the role of product marketer to be one that allowed me to do a combination of these things, and soon landed a job in product marketing at Salesforce.
While there was an adjustment from going to consulting from product marketing, and from professional services to the technology industry, I loved the new challenge and changes.
Most notably, because I no longer was traveling all the time, I actually had time to have a life outside of work. This gave me even more time to explore my curiosities of writing, speaking, blogging, etc.
My energy and inspiration came back online in full force. Because this job didn’t require travel, I had time for more writing and speaking. I had a day job that aligned with my strengths, and I had outlets for creativity too.
Channeling Expertise into a Book
Between having a day job that was more aligned to my strengths and interests, and writing and speaking and blogging outside of work, I suddenly felt significantly more energized and inspired to keep pursuing these interests.
By 2018, I was getting an increasing number of requests for speaking and training, and my blog had grown to over 350 posts. I decided to pour my expertise into a book.
MBA Insider: How to Make the Most of Your MBA Experience chronicled many of the lessons I had learned about school and careers. I interviewed over 60 MBA alums and shared their stories.
The book symbolized how much I’d learned over the past few years. I took pride in that, but it also kindled some introspection.
I’d recently been promoted at work. “Don’t expect another promotion for a while,” I was cautioned.
Is this it? I began to wonder. I was almost five years out from business school and was working for a great company. I was good at my job. To top it off, I’d just published a book. On paper, I had it all.
But I couldn’t shake the feeling that something was missing.
COVID Reality Check
I was growing a podcast, preparing talks for companies and schools, marketing a book, and holding down a full-time job. There was a lot of uncertainty going on in the world, but I was invigorated.
I’d work on my podcast or my training business from 6–8 AM. The hours of 8–5 were for my day job. Before bed, I’d spend another four hours on my side gigs. For a while, I was on cloud nine.
But here’s the reality: Even when you like your jobs, it’s hard to work a full-time day job and a full-time side hustle. My company was going through a lot of internal changes, so my work projects kept getting sidetracked. Coupled with 2020’s health and social justice crises, I was hitting a wall.
My attitude toward my main job was starting to shift — and not for the better.
Time for Change
Self-aware enough to know that I needed a change, I began looking for a new job within Salesforce. I made it to the final round of a position on another team — one I thought was a perfect fit — but I didn’t get it.
I received an offer for a similar position at another company. On paper, it all lined up: right company, right role, right industry and a great team. But instead of being excited, I felt a sense of loss.
For the first time ever, I began to entertain the idea of leaving the corporate path and becoming a full-time entrepreneur. I’d been side-hustling for over six years. While the money didn’t yet match my corporate salary, it was enough to make me consider the leap.
I knew what I’d accomplished so far:
Successful speaking engagements
A growing client list
A podcast, complete with sponsorship packages
Popular online training programs
Sales to multiple Fortune 500 companies and higher education institutions
What could this be like if I pursued it full-time?
As I debated the idea, a close mentor put me in touch with a facilitator and trainer who’d been through a similar transition. After sharing his journey with me, he encouraged me to check out other small business owners with leadership training companies.
I began to see a potential path forward. Even still, I was concerned about walking away from my product marketing career. Two previous managers offered invaluable advice:
Product marketing was the best possible training for an entrepreneur in talent development.
If I ever wanted to come back, I would always have a job.
Cutting the Cord
As someone who had advised thousands of people in their careers, having to make this decision tested a lot of my own beliefs and frameworks about exploring career possibilities.
One of the things that I realized on this reflection was that leaving the corporate path would give me more agency and autonomy over not just the work I do, but where, how and why I want to do it. As a result, I could now be in a position where I could actually create conditions for work that fit within the context of my life, and that I could also, at any given point, exercise my choice and agency to make changes. I enjoy working, a view work and career as vehicle for me to achieve my own goals. It is a vessel for how I live my values, and I hope to be able use that vessel for a very long time. My bet was that I could achieve my own goals and make a greater impact by taking more control over my work through entrepreneurship. While working in corporate had plenty of benefits, I just realized that for me to achieve that vision I would need to create better conditions to make that happen.
Part of this for me, was realizing that through hard work, planning, good decision making and some luck, I was in a privileged position in my life and career to have the ability to be thoughtful about how I wanted to work and what I wanted out of my career. As a student of the future of work, I was trying to actually make this come to life for me, and work in a way that I had been writing and researching about.
Leaving the corporate path would give me more agency and autonomy over how, where and why I work. Through effort, planning, good decision-making and some luck, I was in a position to decide how my work would fit into the context of my life.
So in August 2021, I took a bet on myself and my abilities. I officially left my job at Salesforce and began building my business full-time. I also seized the opportunity to move to LA. For the first time, I was building my work around my life and not the other way around.
Now, I’m about 1.5 years into this journey. I’ve experienced both highs and lows — and shared them here and here — but I’m so grateful that I decided to pursue this path as a solo entrepreneur.
For anyone who’s getting started on a similar journey, I offer the following insights and suggestions.
Lessons from My Journey from Side Hustle to Full-Time Entrepreneur
1)Pay Attention to Your Inner and Outer Game
Navigating transitions requires you to pay attention to two things:
Your inner game: This is your self-awareness of your thoughts, interests, motivations and strengths. It’s what led me to realize that I wanted more from my day job.
Your outer game: This is about being aware of the ecosystem — the people, organizations and opportunities — around you.
When you’re considering a change, balance what’s going on internally with what’s happening externally. By paying attention, you can spot opportunities for exploring projects or taking the next step.
2.Explore and Experiment
I never started my side hustles as a way to make money, nor did I jump into entrepreneurship right away. Rather, I explored things I was genuinely curious about. Each small experiment, such as blogging or coaching, gave me new insights. Those insights fueled additional experiments and opportunities.
Following your curiosities lets you test things and see what sort of side hustle or solo-business you’d like to build.
3.Show Up and Ship
To find new opportunities, you have to both show up and ship.
Showing up means connecting with the outside world and other people. You get to showcase what you’re working on and ingest signals from others. Serendipity happens when others associate you with an opportunity. When you show up, you expand the surface area for opportunities to come alive.
Shipping means doing the damn thing. You can’t think, plan or reflect your way to success; at some point, you have to “ship” your work. For me, that means writing a blog post, interviewing an MBA alum or recording a podcast. Shipping clarifies your thinking and invites feedback. Writing over 400 blog posts and producing 200 podcast episodes has fueled countless opportunities, connections and ideas.
4.Hone In on What Energizes You
Research shows that using your strengths each day increases employee engagement. In fact, when you do things you’re good at (and like doing), you find more joy throughout your whole life.
When my consulting day job didn’t incorporate all my strengths, I took matters into my own hands through side projects. Those activities renewed my energy and excitement.
They also inspired me to look for a job that included more of the things I loved. That’s how I ended up on the path from management consultant to product marketer to full-time facilitator and talent development leader.
5.Focus on Drum Beats
When it comes to exploring ideas or making career changes, we often fixate on lightning bolts — the big “aha!” moments in which we suddenly see the path forward.
But there are also drum beats, the everyday habits and practices you execute consistently over time. For me, that’s every messaging document I’ve produced, every sales enablement training I’ve led, and every interview I’ve done with an MBA student.
Pay attention to the drum beats in your life. Although small, they’ll build over time into a powerful melody. Showing up for the drum beats can eventually lead to lightning bolt moments, such as writing a book or making a career transition.
Conclusion: Enjoying The Journey
The path of entrepreneurship isn’t a game to be won, but a game that allows you to keep playing. I’m still early in the game. I have more to learn and so much more playing to do.
I believe that entrepreneurship is a toolkit. There are many right ways to approach it, and the only one that matters is your own. But I hope this honest account of one person’s path helps you evolve on your own unique journey!
Appreciated learning about your journey, Al! Thank you for sharing.