Feed Your Career Octopus: Tips For Finding (And Keeping) Awesome Mentors

Research shows that mentors are an important and valuable asset for career planning. Everyone from Martha Stewart to Kid President to your high school English teacher can fill the role. Here’s advice on developing those coveted relationships.

Feed Your Career Octopus: Tips For Finding (And Keeping) Awesome Mentors

You’ve just landed your first job.


Or it’s your second, or third, or you made partner, or created your own job and taken the plunge of starting your own business. Whatever the case may be, what is arguably harder than landing a position is finding people who can and will professionally bolster you. People who will support your cause and career. What you need, to borrow from the show Girls, is a Spirit Guide.

You need a mentor.

Actually, everyone needs a mentor. It’s proven that mentoring helps with salaries and happiness. This doesn’t have to be in the professional sense either. Maybe you have friends that mentor you about breakups, or a friend that you can talk to about your family.

However, professional mentors are just as crucial. It’s invaluable to have someone you can bounce ideas off of about your career, and then how that fits into your life.

I am lucky that in my two years since I started my digital PR company I’ve found a whole host of mentors, with different roles and skill sets, all brilliant and shining and impressive. I think of them as a Career Octopus–each arm or mentor brings something different and wonderful to the table.

Finding and keeping someone in your corner is difficult. Here are a few tips that I used in finding and keeping a mentor (let’s hope mine stick around!).


Have a Hero and Do Your Research

Everyone has a professional hero, whether it be a titan like Hillary Clinton or a brilliant local businessperson. Pick a person you’d like to be your mentor, and figure out the best way to get to him or her. Whether or not you get there, there are often people along the way that are actually going to be more helpful. It also doesn’t have to be someone older, just someone whom you admire.

Research is key. What has this person written recently? What has her career trajectory been? If you do end up being connected, be sure to have read all the important pieces so you don’t look like an amateur. Sometimes meeting your hero can fall short of expectations too, so be prepared for that. It might be someone, as I said above, along the way that you didn’t mythologize that is of more help.

When Bethenny Frankel talks about her business inspirations and mentors, she always goes back to working for her idol Martha Stewart on a reality show. She came in second, and in turn learned more about herself and what she needed. Instead of wanting to be Martha Stewart, she realized she wanted to transform her work from a services industry to a multi-million-dollar product.

A Mentor Doesn’t Have to Be in Your Field

I’ve had great mentors and advisers that have tremendous business savvy, but have nothing to do with digital media or communications. Sometimes this is actually helpful–given that this person is able to see the broader picture of your career and business. A lot of those principles are universal. I’m a very small-picture person, so it’s important for me to have someone who helps me see the frame. And the wall. And the house.


Choose someone whose career and drive you admire, and ignore the industry. It might be someone you know socially, or a friend of a friend. Ask to have a conversation, because you never know what could happen. I got fantastic advice from a friend in finance and insurance. While the content was different, the basic business principles he taught me, as well as a lot about business interactions, apply to my business every day.

Richard Branson has mentors for every different area he works in:

Dropping the “M” Word

I’ve read a lot of back and forth about whether or not you should drop the “M” word. (And no, I don’t mean “marriage,” though that needs to be dropped carefully too.) The truth is, this is sort of a marriage, but it’s very important to be aware of what this person can offer you. “Mentor” feels like very big shoes to fill. I’ve been on the other side, and it can feel like a lot of pressure and give you the opposite result–the person might feel overwhelmed. Instead try something like, “I really value your advice, would you be open to continuing the conversation?” Try to play it cool. Whatever you do, don’t use the phrase “pick your brain.” It immediately sounds like you want to use someone.

It’s also really important to know your audience. It’s better to be specific, so that you’re not giving this person a huge task. I’ve gained more partnerships and mentors by specifically calling out one project, like an event or campaign that a person has worked on. Blanket admiration is often too murky.

Be Sensitive and Realistic to Time


Everyone is busy. Period. We’re busier than ever–24/7 schedules, personal lives, no personal lives, working-playing-eating-drinking. But it’s very important to be cognizant once you get a mentor of how much time he or she has to give you. A lot of times, these relationships evolve organically too.

That being said, follow up with what you’re up to. A great mentor of mine told me that she once hired a guy whom she mentored, two years after he first reached out. It was his consistent updates (about every other month) that kept him top of her mind. And she was impressed with his diligence. You’re not annoying someone. (Within reason.)

Mentorship is a Two-Way Street

Just because someone is more “successful” than you are doesn’t mean that he or she doesn’t want advice back the other way. Some of the college students I’ve mentored have great ideas that are just as important as people whose careers I look up to.

Everyone needs a fresh perspective, respective of age or years or experience. After all, some of the best advice I’ve gotten recently is from Kid President.

Related Story: The New Face Of Modern Mentorship


Meredith Fineman is the CEO of FinePoint digital PR. You can read more of her writing here.

[Image: Flickr user Lecates]