2021 Year in Review & Looking Ahead to 2022

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2021 was an up and down year for me, and I imagine that is true for most people. The pandemic continues to find ways to rear its ugly head, people are adjusting to a work from home or hybrid working environment, our political landscape seems to get more and more bleak by the day, and around the world, there are looming threats of war.

By the same token, we have also expressed our resilience in the wake of all of this stress, and we hopefully have an easier time placing things in perspective and expressing gratitude for what we have. We have vaccines now and we are starting to feel more comfortable getting back to our normal way of life.

For me personally, 2021 was a tumultuous year with a lot of change, ups, and downs. I decided to sit down and reflect on the year as a means to coming to terms with everything that happened and preparing for the road ahead. All in all, I’m proud of the way I lived and learned and I am looking forward to incorporating my learnings into 2022.

The year began with a bang, as I had just published my first book, “Authentic Selling: How to Use the Principles of Sales in Everyday Life” in December of 2020. This led to a myriad of interviews and bylines where I was able to better position myself as a thought leader within the sales industry. This was coupled with the completion of my online course, “Weirder Than Waldo,” a training program for Sales Development Representatives on how to tackle the art of cold e-mailing.

At this time, I was living in Cape Cod with my now-fiancee, and was very deep into running a virtual online workout program for myself and my friends. My learning from this was that you can really create anything if you put your mind to it, and that when life deals you tough blows (like not being able to go to a gym), you just have to be solutions-oriented and figure out another way rather than dwell on the negatives.

As we rolled into March, I was able to get vaccinated, which opened up a lot of new opportunities. But the biggest thing that happened that month was the acquisition of Next Caller by Pindrop. I had spent 7.5 years at Next Caller as an early employee and sales leader, and my coworkers were really like my extended family. Working there was the best professional experience I had had to date.

In the aftermath of the acquisition, I decided I was ready for a new challenge. On one hand, this was incredibly exciting because my goal for the company and for myself was to achieve a successful exit, which we did. On the other hand, it was bittersweet because I had established a high level of comfort within that industry and within the company and deciding to do something new was going to be a big risk. Saying goodbye was not easy for me, and no matter where I go, I will always miss the camaraderie I established with my friends and coworkers.

As the year rolled on, so did the ups and the downs. I was fortunate to be approached by former JetBlue Chairman Joel Peterson about a book project he is working on that involved interviewing entrepreneurs and CEOs of major companies. As a fellow author and aspiring entrepreneur myself, this was a great opportunity to learn from a lot of very intelligent do-ers.

On the flipside, I would wind up not really feeling fulfilled in my next job opportunity and feeling a little bit of regret about moving on from something that was more familiar for me. I ended up leaving after only three months. This was pretty challenging for me, as I am often really hard on myself when I make what I feel is the “wrong” decision. This was yet another lesson in the futility of finger-pointing and the importance of looking forward.

What made matters worse is that virtually the same thing happened at my next stop. They say everything happens for a reason, and I was approached for a Head of Sales role with Dvinci, which thus far has been an incredible opportunity. Though I was confronted with the reality of having four W2’s in one calendar year – which is less than ideal – I try to think about the positive. For starters, every time I made a job transition this year, I was not lacking for opportunity. The onus was really on me to do better diligence about makes for a good fit, so I learned my lesson and moved on.

In July, the biggest news of my year happened. I proposed to my longtime girlfriend Julianne and somehow convinced her to say “yes.” We had taken up golf together at the end of 2020 and we were living on a golf course (by the 8th hole) down in Cape Cod. I had arranged for both of our families to be present and waiting on the deck as we teed off on the 8th hole where I asked my surprise question by an onlooking photographer who captured the moment. Her family was supposed to be away that weekend, so she was pleasantly surprised and we planned our wedding to happen next year on Labor Day Weekend in Boston. Speaking of which – we made a decision to move to Boston, and only a few weeks later, we were settled in to our first apartment together.

Throughout the course of the year, I invested very heavily in my professional development, enrolling in the Enterprise Go-To-Market and CRO Schools with Pavilion, reading sales books, mentoring under-represented individuals looking to break into tech sales through SV Academy and Co-Op Careers, and involving myself in go-to-market education and various investment opportunities in high-growth startups through the Emerging Leaders’ Syndicate. My work in the community caught the attention of some high-growth startups and I began consulting and advising startups on the side as a new hobby. This has actually been very informative for me as it gives me the perspectives of various CEOs and how they think about their business, and I imagine it will be useful for me in my new role as I try to bring an emerging tech company into hyper-growth mode. I started podcasts both professionally for thought leadership and in my capacity as Vice President for the Princeton Class of 2010, which was entertaining for classmates who missed two years of reunions. I also got to spend a lot of quality time with my little brother from Big Brother Big Sister in New York City, which also gave me a great excuse to reconnect with old friends in the city.

One of the more interesting experiences of the year was running the Boston Marathon. I had been signed up for the NYC Marathon in 2020 but that had been postponed to 2021 due to COVID. In the summer of 2020, I got an email that the Boston Police Foundation needed fundraisers for the Boston Marathon in October, one month prior to the NYC race. It had been a lifelong dream of mine to run any marathon, but especially the Boston Marathon, since I am from Boston and I had watched it many years in person growing up. Feeling that I could kill two birds with one stone, I jumped at the opportunity.

Running the race was a real mix of emotions. I suffered a condition called rhabdomyolysis which caused intense muscle spasms in my calves starting in Mile 11. These painful spasms persisted for hours until I finished the race. Had I realized what was going on, I would have stopped running. It turns out that rhabdomyolysis can lead to amputation or even death. Naturally, my time was a lot slower than what I was hoping for. This made me very depressed once the race was over. What was supposed to be a joyous occasion had become a major letdown. My bloodwork after the race was concerning enough that I had to pull out of the NYC Marathon.

As time passed, I learned to look at it all a bit differently. Everyone around me was proud of my achievement and even just deciding to run (and finish!) the race. Though the circumstances were not ideal, I had been tough in the face of adversity and had finished a race that most people probably would have dropped out of. I had even resolved to run the Boston Marathon six months later and the NYC Marathon in 2022. So we will see if marathons are a part of my future, but I needed to come to terms with the reality that my training needed to be a sharper focus for me if I wanted to avoid injury. That was a tough pill to swallow, but I learned to view it through the growth mindset as an advancement opportunity rather than through the fixed mindset as some sort of indictment on myself.

As I look ahead to 2022, I have some big goals. I had taken a screenwriting course in 2021 and I am signed up to do another in the beginning of 2022. When I wrote my book in 2020, I had settled on writing about sales because it was less risky. If I married the book to my current career, I could still advance my sales career without entirely dipping my toe into the waters of becoming a full-fledged writer. In 2022, I would like to publish my second book, which is a set of short stories. I feel that this would be a bolder move because that is the direction I ultimately want to go later in life. So better now than later to start getting some critical feedback on my writing.

I also have a massive opportunity in front of me in my career. I have scaled companies that have started from nothing, and now I have an opportunity to help scale a much larger organization that is growing at an even greater speed. It is a new industry that I am passionate about (solar/renewable energy) and a new challenge altogether to learn it, build the network, and to build out a great team. I’m really excited about this journey and the challenges it will present.

And of course, in my personal life, I’d like to execute a great wedding and start planning for a future and a family. This will require great discipline between a demanding day job balanced out with the potential running of multiple marathons, writing a book, staying in touch with friends, and of course doing all of the planning. Fortunately, I have a great partner who knows when to take the lead and how to push my buttons a bit when I need to step up to the plate more. Like me, she is on the ball and very proactive to make sure we stay on top of things. As I try to be understanding to her when she is under a lot of stress, she is always accommodating to me whenever I find myself feeling a bit overwhelmed.

I think if there was one overarching highlight to my year, it is that my family is still together and it is growing. I think the pandemic forced us to really appreciate our families, because we did not get to see each other very much. We did family FaceTimes prior to the vaccines being released and quite frankly probably stayed in touch more than we would have otherwise. Once the restrictions were lifted, I got to share two very special moments with my father, taking him to Ann Arbor to see Michigan (his alma mater) defeat Northwestern, and later on in the season watching them beat Ohio State together at my apartment in Boston. I’ve watched many games with my dad throughout my life and it was nice for once to see him not swearing at the TV. I made monthly visits to visit my grandmother – now 92 years old – who has struggled with loneliness during this difficult time. And I have been overjoyed to welcome my new in-laws and sisters-in-law to my family, and myself to theirs. All this to say, as I go into 2022, it is important to remember the things that truly matter most – the things we often take for granted – and to maximize them to their fullest potential.

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