Kate Lee asked Emily and me to write letters to each other for a series of posts that they are doing at the Medium.  I like the concept of how the Medium is curating at the same time being an open platform for self publishers.  If you missed the piece we it is.

Dear Mom: How Do You Find a Mentor?

Dear Mom,

I’m writing to you as I lay on my bed in what to me feels like my high school bedroom. In front of me is a bulletin board wall covered with photographs of me and my high school friends and images that I cut out from magazines when I was 16. Behind me are boxes filled with belongings that I collected throughout my time in college. In less than a month I’ll be moving out of your and Dad’s house in Manhattan and into an apartment of my own in Brooklyn. I’ll also start looking for my first job.

Having just completed my undergraduate degree, I can now reflect back on my past few years at college. My studies in sociology and English were incredibly fulfilling, and in my last year, I put a lot of time and energy into writing a thesis, which in the end was extremely rewarding. Not only did I develop intellectually, but I also formed meaningful relationships with my peers and professors that allowed me to grow socially as well as emotionally.

I’m lucky to feel so satisfied with my college experience, for that satisfaction has allowed me to feel ready for what’s next. What exactly is next, I don’t know.

I have some ideas about the kinds of jobs I’m interested in and which companies I might want to work for. I’ve always been interested in food, I love to write, and I am fascinated by the ways in which technology has allowed us to think more strategically about where and what to eat. I am aware of what skills I possess. I know that I am extremely organized and good at project management. I’m mostly interested in working at a dynamic, creative organization and believe I can handle many different roles and responsibilities.

I am surrounded by people, including you, Dad, my older sister, many of your friends, and many of my own friends, that inspire me to think and achieve on a daily basis. I’m thankful to have so many people in my life that I love and respect, and to whom I can look for guidance.

Yet I feel like I’m at a point where there’s another kind of relationship from which I could really benefit, one which would allow me to gain the kind of useful insight and invaluable advice that will impact me significantly over the course of my career.

I’m about to embark on a journey that could be rocky to begin with, or maybe even delightfully smooth, but either way, there’s a long road ahead of me. Once you were young and professionally naive like myself, but now you are a successful and established investor who acts as a mentor to many. So I’m wondering, how will I know when I meet someone who would make a good mentor for me? Or, more importantly, what makes a good mentor?

Love, Emily

How to Find a Mentor

And why having a role model is just as important

Dear Emily,

Every night I pass your room on the way to mine. It’s strange knowing that in a few weeks, that room will be an empty shell, left only with items that are part of your past. You are now officially an adult. I feel insanely lucky that I got to watch you grow up and be part of your journey. We raised you to be an independent person, to grow wings and fly. Now the time has come.On one hand, it is bittersweet, yet on the other, I am so excited for you to move into your own place and begin your adult life.

I remember when I graduated from college. Your dad, whom I have now been with since our sophomore year in college (crazy!), and I moved to New York City to start our adult life. We each had a job in hand before showing up in New York. I was to start in the Macy’s training program. It was different then. Every large company came to interview us on campus. People had fewer choices, and most of our friends all had jobs when we graduated. The knowledge of what you could do was limited by where you’d gone to college or how you grew up. Now, people have so many more options and actually know about all the opportunities out there.

We graduated, went on an eight-week cross-country trip in a Toyota Celica, landed in New York, found an apartment, created a space that was ours, and began our next chapter. We felt excited, scared, thrilled, and uncertain all at the same time — just as I am sure you are feeling right now.

You ask about how will you meet someone who will be a good mentor, and what makes them a good mentor.

Mentors are important. But so are role models. Role models are not talked about as much as mentors, but the reality is that role models can make a bigger impact.

As you embark upon your career, I want you to think about that first. Role models are people you can look up to, someone you might aspire to be like. Their impact can only be felt by you. They make you think about your internal goals — the things you might want to share with a mentor.

I had a few women role models early in my career. The first woman I looked up to ran the store where I was a sales manager in Kings Plaza, Brooklyn. She was sharp and tough and commanded respect. I liked how she conducted herself as a straight shooter, and it was obvious that she was well-respected throughout the organization. She wasn’t so much a mentor, but someone I aspired to be like.

The next woman I worked for was very similar, yet she took me under her wing. At this point, I was an assistant store manager for Macy’s in New Rochelle, and she ran the store. She gave me advice on how to look at the businesses I was running, how to manage the people who worked for me, and how to navigate the company (which was heavily dominated by men at the top), and she made sure I was taken care of after she got promoted.

She wanted to pave the way for me, and that was empowering. She was a mentor for a short time but not for long. She moved up into the higher chains of command, out of New Rochelle and back to New York City. We didn’t have email then, or texting, and people didn’t stay in touch like they do today. After she got promoted, someone else came in to fill her role. He was great to work for, but it had been unique working for a woman who was not only a role model but a mentor at the same time — particularly when there were fewer women at the top and more women at the bottom. Being able to learn from a woman at the top who really cared about my success was a gift.

There was another woman I worked for who was a terrible person. She was mean, she couldn’t have cared less if I succeeded, and she was selfish and not my advocate. She was an “anti-role model” — she showed me what not to be. The only reason I stuck it out for a year was because I was learning about the back end of the manufacturing business, and I knew that was invaluable.

I kept my head down, listened, and figured out how to grow my own business inside hers. She never gave me advice, she never taught me one thing, she never even asked how my weekend was. She did not have one social grace. It was like working for a cold tyrant. I was so miserable and stressed that the whole experience took a toll on my face. I developed adult acne. Nobody should have to go through that.

I tell you all three of these stories because each impacted me along my journey.

I was able to work under women that I respected and others that I did not. It helped me become the person I wanted to be — not only in my career, but in my life. They were all role models, some good and some bad.

Mentorship is a word that is tossed around a lot these days. It wasn’t something that people talked about when I started my career. There is this belief that one of the things that you must do when you begin your career is find a mentor. I don’t agree. If people want true one-on-one guidance to help them navigate the world, they should find a good shrink, just like most entrepreneurs see a coach as their business starts to take off. I am a huge fan of that. It can helps people get rid of personal baggage and become better leaders. Mentorship is different. It is something that should happen organically, with someone who finds an interest in you as much as you find an interest in them.

A mentor can be someone older and wiser, or occasionally, it can even be a peer. If you find someone who is older, who you really enjoyed talking to and getting advice, then shoot them an email afterwards and thank them. Begin to engage them by asking their advice on something else that comes along. If it feels natural, then ask if you can get on their calendar for lunch or coffee. It is just like building a friendship.

As for your peer, it might be someone in the same industry as you. You start to build a new friendship or have lunch or coffee during the week. That relationship is built around career talk.

Generally peer mentorship goes both ways, which is invaluable, because you are going through the same thing together and can rely on each other for advice. Later in your career you may even find mentorship from someone younger than you. I see people now who are older but want some transparency into how to code, or into how new technologies work. Younger people can help.

A mentor is someone who can help you think through the stumbling blocks along the way. Someone who can also be your cheerleader. Someone who wants to see you succeed. Someone who is happy to analyze situations with you and give you advice to get to the other side. Someone who has opened the door to you to begin a friendship around your career.

Sometimes that person reveals themselves to you over time, and then all of a sudden you realize that they are your mentor. It makes them feel as great about giving advice as you feel about getting it.

There is a woman you met recently, in Los Angeles, whom I met later on at a party. She thought you were amazing. She said to me, “I want to hang with Emily.” You liked her, too. She has had an interesting career. She is 15 years older than you. If you emailed her and asked her for some advice through this process of finding a job, she would probably be thrilled to do it. When you start to talk to a company more seriously about taking a job, just ask her if you could get on her calendar for a phone call and say you’d love some advice and wonder if she’d be willing to give you some. You are trying to make some decisions, you really enjoyed talking to her when you met, and was hoping she’d be willing to take some time out to talk again.

She could become your mentor without you realizing it. That is how it should happen — organically. If she said she is super busy right now, that is OK. Then she is not your person.

I have always been open to helping others think about their careers. As an angel investor in over 85 companies and counting — where 75 percent of the entrepreneurs are women — I have become a mentor to every person I invest in. I am closer to some than others, yet I make myself available to every one of them and let them know I am there to support them. These relationships did not happen organically, but I work to make sure they know that they can call on me anytime.

There is one woman whom I consider myself a mentor to, and I consider her just as much a mentor to me. She reads my blog. That is how we met. She emailed me asking for some advice about her career. I emailed her back. She took the advice and it paid off. She emailed me letting me know. I was thrilled for her. She wanted to meet for lunch, so we did. Over the years, not only have I have met with her, given her advice on how to negotiate a raise over two days of an email exchange, helped her to think about her future, and applauded her successes, but we have become friends. She has taught me a thing or two about the business she is in as well, and that makes for a great relationship.

You have great insights about people. You will know when to connect with that right person to help you on your journey. You will know who’s a good role model and who’s not. I am confident that you will find your own path and surround yourself with good, smart, caring people.

I am your mentor for life, and hopefully a role model too. I can’t think of anyone else I’d rather be a mentor to, except, of course, your brother and sister.


Comments (Archived):

  1. Shelly Lipton

    All I can say is wow. You both articulated your views so eloquently. What a pleasure to read. Thanks for sharing.

    1. Gotham Gal

      Thanks Shelly

  2. JLM

    .The Force is powerful in that one. You did good, Mom.As to a mentor?I think she already has one.JLMwww.themusingsofthebigredca…

  3. pointsnfigures

    Awesome read for me. Especially as I get ready mentally to mentor in Chicago TechStars again. I think it’s sometimes tough to mentor your own kids. What’s the old saw? “When I was younger, I thought my parents were pretty dumb but when I got older I couldn’t believe how much intelligence they gained over the years.” or something like that…..

    1. Matt Kruza

      follow up to that is: that statement is usually uttered by those people when they become parents 🙂 (maybe a Freudian analysis would say that parents say that so they think they are smart with their kids now… half teasing, but honestly no one my age, 27, says that).

  4. Marissa_NYx

    Beautiful! Thankyou for sharing. The pride & joy on both your and Emily’s face at her graduation shines through. You’re both role models for a trusting, awesome mum-daughter relationship.

    1. Gotham Gal

      Thank you

  5. William Mougayar

    Well done on both ends. I read it last week when it came out, and enjoyed it!

  6. awaldstein

    This touched me.My dad was my mentor as a very young adult. I lit a Yahrzeit candle for the 32nd time for him last night.I felt more thankful than sad. My highest testament to how great a mentor and father he was.

    1. Gotham Gal

      thankful is much better.

  7. Sofia Papastamelos

    This is beautiful, thanks for sharing! I am lucky to have had some great mentors in my life. Funny how those relationships can develop so organically.

  8. Mario Cantin

    I got teary eyes reading this. That’s all that needs to be said.

  9. Pranay Srinivasan

    You guys are a powerhouse on the same page.

    1. Gotham Gal


  10. Alan Clayton

    This is fascinating because it highlights the common misunderstanding of what mentoring, coaching, & training actually are, and how they differ. Mentoring for me has always been a process where the responsibility for progress lies with the mentee. In fact the menthe chooses their mentor (not quite ‘hero’ but not far off) and takes action. Mentoring is about IDENTITY “who am I becoming” rather than “what am i achieving”. Coaching is about “what’s important”. The coach shares the responsibility for progress. The coachee brings commitment to achieving a significant goal; the coach brings the process tools to get there. Training addresses the “what am i good at” and involves transfer of skills, with little concern for whether the student puts them to work or not.I agree with you – mentoring is NOT what a lot of ‘mentors’ do !!

    1. Gotham Gal

      no doubt these words get tossed around these days and everyone feels that they must have a mentor. not sure why

  11. Josh Maher

    Great stuff from both of you! These things are so critical and too often overlooked. I struggled a lot with mentors and role models growing up and never had advice like this on how to think about them or even begin to approach one.Looking forward to the rest of the series!

  12. rh

    Reading this from asia it is a very open and great common sense advise. Mentors come under many garbs but someone who is open, listening and not pontificating is someone who is aspirational.Unfortunately here in asia one commonly runs into the “queen’s syndrome ” where talking to or talking down constitutes giving advise.

    1. Gotham Gal

      talking down to someone never feels good.