Taking the Entrepreneurial Leap

I recently stepped away from my comfortable Silicon Valley tech management career to pursue the unpredictable life of an entrepreneur. The comparison that comes to mind is swapping out my Tempurpedic mattress for a camping mat. So, why in the world did I make this jump? It is a question I get asked frequently these days and often from those who’re anticipating this move for themselves.

If you’ve been considering making such a change, there are articles galore online on why one should or shouldn’t, as well as on signs of readiness. So, instead of reiterating what’s been said before, I’ll use this post simply to share bits of my journey and hope that it helps you with yours.

To be quite honest, Maslow’s apex had been calling out to me for a while and I tried various methods to reach my version of “self-actualization”.

• I gave a fair chance to the tried and tested moonlighting method — you know…the typical advice for entrepreneurs is to tirelessly explore their effort on the side while continuing a full-time job. Realistically, with 2 little ones and tech management responsibilities, there was just no “tireless” left in my day. Much of my leftover mindshare was spent on figuring out how to better juggle the already full life of a parent and techie. Hence, the efforts I tried to kindle usually went out just as soon as I lit the fire and I knew that this model wasn’t going to work for the next 10 years.
• I also tried a baby-step career change to see if that would be more fulfilling — I was a bit bored from the “Rinse and Repeat” of my product development career as most projects offered similar challenges, just wrapped in a different set of technologies. After meticulous soul-searching and self-reflection, I landed on a TPM (Technical Program Manager) career as a potentially good fit to try. This was a low-risk career change from Engineering Manager, still tapping into my skills and experience but offering a new set of challenges. As good as it looked on paper, it just didn’t work out in practice and I appreciate having learned a few new things about myself.
• I felt successful and could afford a bigger risk — it’s important to note that I felt more or less successful at my career with occasional ponderings about my place on the corporate ladder. All in all, I felt satisfied with my struggles and accomplishments. If I ever doubted myself for not aiming high enough, those fears were allayed when I visited my high school last year becoming keenly aware of how far I had journeyed in the last 25 years. Given this feeling of success, it felt ok to take on a risk to try something riskier.
• If all else fails, I’ll have enjoyed the journey and there are other perks — A few years ago, I had to abandon my Mt. Shasta hike and turn around part-way due to altitude sickness. Although I didn’t make it to the summit, it remains one of my most memorable of the many hikes with my husband. What’s more, it led to the unique perk of exploring the town of Mt. Shasta on my own, relaxing by the lake, shopping in the quaint downtown and enjoying room service late into the night. Similar to this experience, even if I don’t succeed at reaching the destination, I expect that my entrepreneurial journey will be a memorable one with perks such as the flexibility I’ve always craved as a parent.

As I was considering this move, I had a vision that I was standing at the edge of a cliff, prepared to jump but contemplating if I would make a safe landing or ever recover from the fall. My son overheard and contributed this nugget of wisdom that only a child’s carefree imagination could concoct — he said there was obviously a trampoline at the bottom of the cliff and even if I didn’t make it back to the top, I’d enjoy bouncing for a while and could get launched onto another hilltop with more interesting places to explore. I suppose that sums it up pretty nicely! My only real failure would have been to wait at the edge of that cliff forever and being unable to take the leap.