Twenty years. It feels like both a lifetime and the blink of an eye since I first stepped onto the corporate ladder with an eager, if slightly naive, stride. Back then, the world was a different place – no smartphones in every pocket, dial-up internet was still a thing, and “AI” was mostly a movie plot. If I could, I’d travel back in time to that younger, ambitious version of myself and share a few hard-won truths. Not to change the path, but perhaps to make the journey a little less arduous, and a lot more insightful.
This isn’t about regret; it’s about reflection. It’s about distilling the essence of two decades navigating boardrooms, leading teams, celebrating wins, and learning from stumbles. These are the three pillars that stand out: Mentorship, Mistakes, and Moonshots.
1. The Unsung Power of Mentorship (and Being Mentored)
When I started, I thought mentorship was for other people – for those who needed a leg up, or perhaps weren’t confident enough in their own abilities. How wrong I was. I wish I had actively, aggressively, and shamelessly sought out mentors from day one.
- It’s not about finding a guru, but building a council: I spent too long looking for that one perfect sage. In reality, different mentors offer different lenses. Some for strategic thinking, others for people management, some for navigating corporate politics, and some just for a good gut check. Cultivate a diverse network of trusted advisors.
- Mentorship is a two-way street: I also wish I had understood sooner the joy and responsibility of being a mentor. It’s not just about dispensing wisdom; it’s about continuous learning. My mentees challenge my assumptions, expose me to new perspectives, and keep me grounded. The best way to solidify your own learning is to teach it.
- Seek out uncomfortable truths: The best mentors aren’t cheerleaders; they’re truth-tellers. They’ll tell you what you need to hear, not just what you want to hear. Embrace those moments of candid feedback – they are gold.
2. Embracing Mistakes as Master Teachers (Not Marks of Failure)
Oh, the mistakes! From misguided product launches to misjudged hirings, from botched presentations to overlooked market shifts. In my early career, each error felt like a personal failing, a mark against my record. I wasted so much energy dwelling, regretting, and trying to bury them.
- Mistakes are data points, not destiny: I wish I had viewed every setback as a rich source of data for future improvement. What went wrong? Why? What was my role? What could be done differently next time? This mindset shift transforms “failure” into “feedback.“
- The speed of recovery matters more than the absence of error: No one gets it right all the time. The true measure of a leader isn’t never falling, but how quickly and gracefully they get back up, apply the lessons, and move forward. Develop an institutional muscle for post-mortem analysis and rapid iteration.
- Transparency builds trust: Early on, I was tempted to hide or downplay mistakes. Now, I understand that acknowledging errors (when appropriate and with solutions in mind) actually builds credibility. It shows humility, resilience, and a commitment to learning. My biggest lessons often came from my biggest stumbles.
3. The Audacity of the “Moonshot” (and Why You Need One)
For too long, I focused on incremental improvements, on hitting quarterly targets, on optimizing existing processes. All important, of course. But it took me a while to truly grasp the transformative power of a “moonshot” – that audacious, seemingly impossible goal that forces you to rethink everything.
- Moonshots define your North Star: A bold, long-term vision isn’t just a marketing slogan; it aligns your team, fuels innovation, and gives purpose beyond the day-to-day grind. It helps you say “no” to distractions and focus resources on what truly matters.
- They unlock dormant potential: When you set an impossible goal, people stop thinking incrementally and start thinking fundamentally differently. It fosters creativity, encourages risk-taking, and reveals capabilities you never knew your team possessed.
- The journey is the reward: Even if you don’t perfectly hit the moon, the journey of attempting it yields immense learning, develops new capabilities, and cultivates a culture of ambitious thinking. The process of striving for something extraordinary often creates unforeseen opportunities.
If I could sit across from that younger me, I wouldn’t tell her the lottery numbers or which stocks to buy. I’d simply say: Embrace the uncomfortable wisdom of others, learn fiercely from every misstep, and never shy away from aiming for the seemingly impossible. The journey will be richer, the impact greater, and the lessons, truly unforgettable.
