A Few Things I Have Learned From Mentorship

A year and a half ago, I decided to commit myself to mentorship. There were a few reasons for this.

First and foremost, I have been very fortunate in my life. I come from an upper-middle class family, my parents supported me in absolutely everything that I wanted to do, and they paid my way through a very competitive private all-boys high school and Princeton University. To be clear, I worked incredibly hard at every single turn – and those who have worked with me will say that I have a motor unlike any they have ever seen – but that does not change the fact that there are those who have similar work ethic but never realize an opportunity to show it. I also have other inherent privileges and took to heart my high school’s motto, “From those to whom much has been given, much will be expected.” I have known for most of my life that I should pay it forward to those who may not have had the same opportunities that I did.

Second, I recently have been the beneficiary of mentorship and have realized the profound impact it has had on me. I have sought out professional and personal advice from a lot of people over the last few years, and I actually started to resent the reality that I had not taken it upon myself to do so earlier in my career. Specifically, I have a great mentor, Bob Almond, who is an executive at a technology company in Boston. Over the last decade, he has helped me in a variety of professional and personal situations, and seeing what kind of impact that has had on my life, I’ve felt a sense of duty to give what I can (my experience) to others.

Lastly, I think in today’s day and age, we are more privy to and awakened to the realities of the disparities that capitalism has created in our country. I am by no means a “social justice warrior,” and, in fact, I am a big proponent of capitalism, but that does not change the fact that it has flaws and seems to leave certain people behind. I have become more interested in the democratization of things, like Robinhood for investing, for example. And I think it is important that those who have the time, energy, and willpower do whatever they can to democratize their experience.

I have done a few different things in terms of mentorship over the last couple years. First, I started out with The Big Brother Big Sister program, which assigns an adult mentor with a teen or pre-teen mentee who needs such a figure in their life. For reasons related to privacy and how the program works, I can’t speak too much about my mentee, other than to say he is a teenager in New York City and that I have really enjoyed getting to know him. Even though I left New York City amidst the pandemic last March, I make an effort to go back and see him once a month, and our bond has only grown stronger over time.

The other type of mentorship I have embarked upon is professional mentorship through programs like SV Academy and COOP Careers, which are for under-represented individuals looking to break into tech sales. This is vastly different from BBBS, which is more of a personal mentorship for younger people who need a role model. For whatever reason, tech has become something of an elitist industry. If you do not have experience in tech, it is very hard to break in. It makes little sense to me, as everyone who works in tech at one point had no experience in tech themselves, but it is what it is. I do what I can to try to help people who are generally underrepresented in the field and it has even led me to opportunities to mentor other professionals who are not affiliated with these programs. You might think mentorship is a one-way street, but I learn just as much (if not more!) from my mentees than they learn from me. I want to share some of those learnings here:

• Do not make excuses for yourself

Something I have learned from mentoring people professionally is that you should never make excuses for yourself. Let me dig into that a little bit more.

I ask anyone I hire “What is your ‘why’”? In other words, why do you want to succeed in your life? What is it that you really want in your life and why?

The answers to this question are often surface-level and require peeling the onion. For example, most people say they want to make a lot of money. But that is obviously not the real reason, because money in and of itself does not give us anything. For some people, it provides financial freedom and an opportunity to pursue a riskier career path. For others, it affords an opportunity to travel. Then there are people like some of the mentees I have had who are first generation Americans whose parents had to work multiple jobs growing up, or those who had to work in restaurants their entire childhood to support their family, or things of that nature. In these cases, my mentees understand the value of money and what it is like to have to make every single sacrifice to put food on the table. For them, it is personal, and it is about creating a better life for themselves and their families.

Hearing these stories from my position of relative privilege, I have learned to never make excuses for myself. When I put my problems in perspective, they seem relatively minor compared to, say, having to delay your college education so that you can work a couple jobs to support your family. That is something lost on all of us: we all have problems. We often associate those who are “well to do” with easy lives, but the reality is, that is hardly ever the case. We all have problems, and what defines us is our attitude towards them and how we handle them.

One of my mentees once went out of his way to say to me, “I don’t want anyone to hire me because I am black. I want to be hired because I earned it, plain and simple.” I was taken aback by this, especially because he kind of said it out of the blue. This person had a tremendous sense of accountability for things that were ongoing in his life, and he did not want anyone to feel sorry for him based on immutable characteristics beyond his control. He wanted instead to be judged based on the content of his character, his work ethic, and the value he could bring to an organization.

• We have much more in common than you might expect

I think today’s dialogue is pretty unhealthy, and that was a major impetus for me to write my book, “Authentic Selling: How to Use the Principles of Sales in Everyday Life.” The combination of a biased and irresponsible media with social media companies who are interested in driving us against one another is an utterly terrible amalgamation. It would make you think that we are all more different than alike, that many of us are good while many of us are evil, and that we are mostly not interested in the same outcomes.

The truth could not be any more different. Regardless of whatever your politics are, chances are you more or less want the same things. You want you and your loved ones to be happy and on a high-level, you want others to be doing well, too. We just often disagree about the best way to accomplish those outcomes.

On paper, I am very different than my younger brother in the BBBS program. But ultimately, we have a lot of things in common, and we relate to each other based on those commonalities. In the interest of privacy, I will not say much more beyond that, but suffice it to say that you only get a chance to realize what you have in common with others if you give them a chance to begin with. Unfortunately, many people today do not even bother to give others a chance. Despite being told for the last several years that you must have a “lived experience” in order to be qualified to speak about an issue, I was lectured and repudiated by non-Jewish friends of mine when discussing what I find to be anti-Semitic in the backlash surrounding the recent Israeli/Palestinian conflict. This was profoundly disturbing and upsetting to me.

The same is true in my professional mentorship experience. Most of the people I work with have a variety of different backgrounds, and very few resemble anything like my own. I am sure we hold vastly different beliefs on all sorts of things. But we relate to one another because of a shared value system and a shared experience. I cannot stress enough how much we as human beings treasure shared values. We are biologically hard-wired to protect people who share our values. Remember that next time you meet someone who seems very different than you. Chances are, you have some shared values or shared experiences, you just need to be patient enough to identify them.

• Appreciate those who want to do their best

I think by virtue of even seeking out a mentor, it means that someone is something of a self-starter. Think about it: it requires a certain level of humility to put your ego aside and to say to yourself that you need someone else’s help to get to where you want to be. I have had to put my ego aside when hiring consultants in the past or asking people in my field for advice. When my mentees spend time working with me, they are doing the exact same thing.

Having that sense of humility and the desire to get better inherently says something about someone. It means that they want to do the best they can in their life. It is hard not to want to help people who very desperately want to help themselves. It is people who do not try very hard – especially those with relative privilege – who we tend not to admire very much. It is why we always root for the underdog in sports.

• It does not take much to make a big difference

This is the last and final point, and I am closing with this one because I want to encourage people who are reading this to think about doing something – even if it’s very small – to give back.

Many of us feel we are not equipped to be mentors because we do not feel that our lives are particularly special. When you live your own life every day, it certainly feels pretty bland to you. Realistically though, we are all very interesting people if you peel the onion, and people who are different we often find to be the most fascinating. We all have our own experience that we have lived, and whether or not it feels very exciting, our experience is the one thing we all have that we can give to others. We can all find value in each others’ experiences.

It takes very little time to make a huge impact in someone’s life. For my mentees, I often will post their resumes on some job boards I am part of. They usually wind up with a half dozen interviews as a result. This takes me all of two minutes to do, but yields tremendous impact for my mentees. Simply because I have a level of access that they do not am I able to accomplish this for them. It is just about taking the initiative to make that small gesture.

All this to say, it does not necessarily require hours and hours of time to help someone. It can be one conversation with a specific takeaway or one specific gesture that opens the door for someone. For a lot of people, they are literally just one step removed from being where they want to be. You can be the person to unlock that door.