My Diary of a CEO

How a Cold Email Changed my Mind

Last year, I had a personal conversation with a top executive of a major company as nothing more than a mid-level management employee. I had reached out to him in a career-building effort with the charming guerrilla networking tactic of a LinkedIn friend-request and a cold, yet friendly, email introducing myself. By all accounts, I should have never crossed his path so early in my career. And, yet, not only was my effort to make contact noticed by him, he offered his time to get to know me and my aspirations in the company. What was supposed to be a brief 30-minute call, ended up being an hour-long discussion about–what turned out to be–our similar passions, values, and the principles which govern our lives. 

That fateful conversation, fortunately, didn’t result in the promotion/career pivot I had aimed for. I say it was fortunate because the thoughts, insights, and encouragement shared in conversation with that executive changed my perspective on my life and career. A change so profound it would have made a promotion by him a prison for me later down the line. 

Here is some of what I learned:

A person who sees your potential and wants the best for you will never clip your wings or put you in a box, even if you ask. After I expressed to him about my love for people and my interest in teaching philosophy, writing fiction and nonfiction books, and how I created a platform to do so, he admonished me to keep after it. We had identified with each other on account of our love for humanity and leadership–which he felt were both rare traits in the world. He said that a part of him wanted to be selfish and keep me enmeshed in the company but it was clear that there was more for me. He had translated his own love for people in how he led and taught leadership in the company. And while he could have done way more outside of his job description, he had decided to settle down as his retirement years were approaching. 

Bet on yourself before you bet on a company. I am not dissimilar than any other 25 year old when it comes to matters of job and career. The pressure of financial security and the rolling tide of bills makes it easy to forget the long-term goals of building an ideal future and, like many, I fell into the rat-race of day to day living. And, like most, I also deluded myself into thinking that a corporate job was what I needed to break the cycle. I had amassed the skills needed to survive and I had grown comfortable with my ability to work hard and move up the ladder, but pursuing my desired future was what I truly wanted and feared the most. It would mean that I would have to bet on myself. It would require me to be more disciplined in honing my craft, have a more defined vision/end-goal for my projects, and–most importantly–be consistent throughout the process. Yes, I could climb the career ladder if I wanted, but it was in my best interest to keep my true aspirations at the forefront of my mind and pursue that in earnest instead. 

Pay just as much attention to the regrets of a successful person as you do their accomplishments. He never explicitly admitted to me that he admired the position I was in with youth and time on my side or that a part of him wished not to settle into his career. He did not have to. The admonishment to pursue my goals outside of the company, the excitement he shared with me in my desire to connect with people through my work, and the candor in him not immediately giving the new job title that I thought I wanted, told me he wanted me to avoid the same pitfalls he’d fallen into. There is much value to be gained when we study the success of an individual. Hundreds of podcasts, books, and videos exist dissecting the positive actions that lead to affluence.  But some of the rawest forms of gold can be found in gleaning the lessons of regret after that success was gained. I had to ask myself, “If I followed this blueprint, is this truly where I want to be in 20 years?”

When I closed the tab out on our conversation, I sat back in my seat both invigorated and terrified. I had never been more happy to not get what I wanted.  I was invigorated because it was the first time I was seen by a stranger similar to myself that understood my most fundamental aspirations and dreams. Most people that thought they saw me only saw the engine of power to champion their causes, their ideas, their politics. I was encouraged to not play smaller than what I truly wanted to do with my life. However, it was equally terrifying because the path that I knew I needed to walk had no preset rules, expectations, or check points of success. I would have to define the metrics for myself and measure and direct my steps based on what my heart truly desired. It was a realization and remembrance I didn’t know that I needed.

Despite the rapport we had built, I never ended up talking to this executive again. I do not believe that I was supposed to–at least not any time in the near future. I had gotten the nuggets of wisdom to navigate on work and career at my current stage of life. But I’d like to hope that someday, when I start to reap the reward for pursuing my dreams, he will somehow come across this piece. I wish for him to know the role he played on my journey and that his journey isn’t even close to being over either–it is just beginning. It is spectacular what can happen in a singular, fateful conversation. It quite possibly can change your perspective and, in my case,  it all happened because of an ambitious cold email.