This post is brought to you by Sidebar: peer-to-peer professional development platform.
In 2019, at 33, I walked away from my last full-time job.
Not because I was failing in my career—in fact, quite the opposite. I became a VP in my late 20s, led large teams, and held high-impact roles, all while starting a family with two kids and having an incredibly supportive partner. To outsiders, it seemed like I had it all.
But in reality, I was miserable, feeling like a failure in every aspect of my life:
As a Mom: I was crushed by mommy guilt, feeling I wasn't spending enough time with my kids and missing all of their firsts. I desperately wanted to do more, but couldn't find it in my busy work schedule.
As a Partner: I had little to none quality time with my husband, because any little spare time outside of my work was spent on my kids or trying (key word, trying) to sleep.
As a Friend: I lost all my friends because I never had time for them.
As an Individual: I was losing a sense of who I am. My career started to define me, and I found myself stumped when asked: what do I do for fun? The answer was ‘nothing’ (or really… I work for fun). And how could I have, when my only free time was during my drive home (pre-covid days, heh), which isn't enough to maintain a sense of self.
My health was declining rapidly. First, I lost the ability to sleep through the night, then my mental health deteriorated, making me short-tempered, agitated, and perpetually exhausted. Unhappy.
Then, I got WHOOP which measures your Resting Heart Rate and Heart Rate Variability and it showed I had vitals resembling those of an 80-year-old woman 😲.
This was the last straw.
The job wasn't making up for these personal losses.
Instead, the workload was soul-crushing, and expectations kept rising. Leadership is glorious and prestigious from the outside, but has its dark sides, including stress and overwhelming pressure. My body was not coping well with any of it, making my daily life unbearable.
I questioned if this was the life I wanted. Was my professional career worth it? Would I regret these choices when I got older?
The sad truth about corporate life is that my experience is more common than we’d like to admit. Many executives feel burnt out and unmotivated, with priorities out of whack, all for what? A fancy title and a claim to making a company loads of money? Is this really it?
Traditional corporate ladder - the only option?
The only well-known path for many, and definitely for me at the time, was to climb the traditional corporate ladder: reach a leadership position and stay there. Yet, traditional full-time roles were clearly not working for me. But I loved my work—it was truly my passion and hobby.
So, what about those of us who love what we do but don't fit into traditional full-time roles?
Uncharted territory.
This is where my story takes a turn into uncharted territory.
So, back to May 2019: I quit my job with the hope of trying something different. I remember being terrified, sad, and unsure of my choices. Yet relieved. But mostly terrified. The lack of the predictability and vast unknown was gut wrenching.
At the time, I wasn’t thinking I was done with full-time work. However, I did leave without anything lined up because I couldn't bear the thought of jumping into another similar role and continuing down my personal death spiral. I was hoping to find the ‘right’ culture where I could flourish. But I didn’t know how to find such a company. The normal interview process is so broken, with both sides just in 'sell’ mode, optimized for signing the contract. So, I initially thought of advising as a way to 'try before you buy' a role. This approach would give me breathing room and hopefully lead to the discovery of a sustainable full-time role in a supportive culture.
But as I began advising, I started questioning my end goal. I found the advising work highly engaging, as it allowed me to utilize my strengths, such as pattern recognition and adding strategic perspectives. For the first time, I could clearly see the frameworks and outliers—it was invigorating. I also received positive feedback from my clients, who said that their time with me was the most impactful part of their week! This hit my north star metric: insights per minute.
Perhaps even more importantly, for the first time, I could close my laptop at the end of the day relax. Truly relax — even taking an occasional nap (gasp!). I was able to invest in my health by going to the gym (yay Crossfit!) and be more present at home—picking up my kids from school, attending their activities, and having date nights with my husband. I felt alive!
A question swirled in my mind: What if I could make a living from advising?
It’s not that simple.
The upsides of advising were clear, but there were also downsides. For instance, stepping out on my own was brutal on my identity: I no longer had the comfort of a traditional job title to explain what I did. Whether I liked it or not, my sense of identity and self-worth was closely tied to my career success at the time. In other words, my career defined me, in more ways than I was willing to admit to myself.
But it wasn’t just my perception of myself: As a solopreneur, your market value is directly related to your personal credibility and experience. People hired me for my expertise, so I felt I needed to find a way to keep growing and learning.
There was also the question of longevity: Could I really keep this up? Being the growth professional that I am, I was constantly asking myself the question: Is what I’m doing sustainable and predictable?” Fortunately, the experience that made me ask that question also gave me some hints about how to answer it.
In order to mitigate these potential risks, I created an intentional strategy:
1. Structuring my advising work to maximize learning. Advising is magical in the sense that it allows for more pattern recognition than a single job. I can have a view into ~10 companies at the same time, clearly seeing frameworks, patterns, and outliers. But I needed to stay heavily involved in the company in order to do so—none of these monthly theoretical check-ins where I had no idea what was happening and could only provide theoretical answers. So, to ensure I could continue learning and provide meaningful advice, I created constraints for my advising roles: engagements needed to be at least 6 months long (to see things through) and include frequent touch-points (meet at least once a week).
2. Taking on full-time roles, but on my terms—as an interim leader. Interim roles are similar to full-time positions in the sense that you are a legitimate member of the team, but there’s a predetermined end date. As an Interim Head of Growth, I make my contracts 1 year long. This allows me to come in, validate the company's hypothesis, learn, create new hypotheses, begin executing, and then develop a succession plan to hand everything over to a full-time hire. After a year, I’d take at least a 6-month break to recharge, focus on advising again, and explore any new opportunities.
3. Creating alternative income streams. Again, to use a growth perspective: my pipeline volatility meant that I needed to layer in additional monetization motions. For me, that meant generating passive income by creating classes with Reforge. So far, I’ve done four programs:
After a year of this new model, I was all in. I felt fulfilled, I saw my pool of opportunities expand, and the system I’d built was starting to compound in value!
Over time, new frontiers began opening themselves up: opportunities like creating and monetizing my blog (see how I went $0-30K in 6 months), paid speaking gigs, LinkedIn post sponsorships (did you know companies will pay you thousands of dollars to co-create content!?), and paid workshops came my way. I even have my own pricing page now!
Speaking of which, special offer time! Because… Black Friday.
If you enjoy reading my blog, here's your chance to get 50% off my paid subscription! Gain access to all of my archives, as well as new, special posts available only to my paid subscribers. Available through this link ONLY.
Now, nearly five years into my solopreneur life, it's really working for me. My health has improved significantly (my whoop stats are 40%+ up!), I sleep 7+ hours through the night (unmedicated, I have to add), I'm more present and happy with my family, and I even (gasp) have some friends again.
None of this is to say that it’s all magical.
Solopreneurship involves tons of challenges—everything from the obvious ones like inconsistent income (especially at the beginning), to more subtle ones like the need to be regularly self-promoting, to the weird ones like having to come up with a succinct answer for every relative, old friend, or stranger who asks “So, what do you do?”.
But has it been worth it for me?
Absolutely.
Stepping out on your own is not for everyone. There’s nothing inherently wrong with corporate jobs—if you’re loving life in a traditional role, I’m excited for you! But exploring career options and taking control of how you monetize your skills is something everyone should consider.
My path is unique to me, and I hope to inspire you in finding yours.
Edited with the help of Jonathan Yagel, storytelling magician.
I love the authenticity, humility and transparency in this post. You chose to make yourself vulnerable. In doing so - proceeding to do something despite fear of repercussions - you showed true courage and great strength. Inspiring stuff! Well done, and Thank you.
Thanks Elena. You inspired me to move forward :)