When I was using dating apps, I would happily approach men to ask them out. It was no big deal. I figured that this was modern dating and that meant I could make the rules.

Asking 49-year-old Jane to be my mentor was, on the other hand, absolutely terrifying. We’d met by chance when she’d stood in for her ill colleague whom I had originally intended to interview for a story. That day, like so many days around that time, I was overworked, stressed, tired. I almost cancelled.

When I look back now at that first meeting, I often describe it as a great first date of rom-com credentials: it was chance meeting, we were passionate about the same things and we could have talked for hours. The meeting was meant to discuss the future of flexible working but I remember we spoke a lot about Hillary Rodham Clinton. 

She gets it, I thought. She gets me. We’d clicked. 

We went our separate ways and for a few more months I persevered in a demanding job that I’d given 150% to. The company was growing and changing and I felt very ready for the next step but I had no idea of where to even begin. A woman in HR could see my frustration. “Have you thought about a mentor?” she asked me. I had, but where do you find these women? Pluck them off the street? Stalk them on social media? I knew I needed guidance and support but I had no idea where to find it. After our conversation I went back to my desk, and there, as if dropped by a smiling stalk, was an email from Jane, saying hi and commenting on a story I’d written. It was a sign: I had to ask her to be my mentor.

Staring at my laptop and a blinking cursor, it felt like I was asking her out – but it wasn’t just pride on the line but my professional credibility, too. Why would this smart woman give her precious time to me? And what does she get in return – a whinging, navel-gazing millennial? Thank u, next. But I was desperate and so was my email, that read something along the lines of “Dear Jane, you are very cool. Will you be my mentor? We could have breakfast once every five years or whatever is convenient but obviously, you totally don’t have to. And obviously, you’re probably far too busy. In fact, pretend I never said that. Sorry. Bye.” 

To my amazement, Jane replied and said she’d happily meet. She’d travel into central London for 8am to have a coffee with me before my working day. I remember quite clearly one of the first things she said to me: “There are two types of women in this world: the women who help other women and the women who don’t”. I knew which camp she was in (and possibly even running).

And so we continued to meet. She had an entirely different background to me – I had deliberately looked for a mentor who was an outsider to my industry, as I knew they would be able to see the media at arms length and offer a clear-headed view, unpolluted by the politics and ego of journalism. From Jane, I wanted someone who could help me develop non-industry specific skills such as confidence, self-belief, negotiating, a better business sense, a way to connect and engage with opportunities, the notion of building my own identity. Her expertise in global marketing was ideal – she knows how to get s**t done, she’s a phenomenal communicator, she’s bursting with energy and ideas and she is full of razor sharp insights. On top of that, she loves a glass of wine, and as an American in London, she is doing her damnedest to bring down Trump. I’d struck gold.  

Over the last two years Jane has helped me on everything from deciding which opportunities to take and pursue, to how to respond to an email and see potential for work in people and places I might previously have missed. She’s turned my ideas, thoughts and hopes into an actionable plan. She’s offered advice on dealing with tricky people and hard circumstances. And most of all, she’s always been there for me; a thoughtful text, a phone call, a link to an article about HRC or Gloria Steinem. 

Over two years, Jane has become a friend, and having her in my corner has made a big difference. Thanks to Jane, I found the courage to go freelance; thanks to Jane I have a plan and a strategy for the year ahead; thanks to Jane, I have reflected on hard lessons and endeavoured to go about things differently in the future. I know that I am more focused, strategic and ultimately more successful because of her. 

Recently, I connected a woman I know professionally with a friend looking for a mentor (Jane has always introduced me to helpful people and it’s something I’d like to pass on). Unlike Jane and I, they share a similar business background. After an initial coffee, my friend took the plunge and asked out this inspiring business woman with 20 years experiencing of building successful companies and selling them. And she said yes. Now they meet regularly, as my friend begins to build her very first business.

Finding a mentor certainly isn’t easy, but you’ll definitely never get one if you don’t ask. So take a deep breath… and click send. 

How to find a mentor

• Know what you’re looking for. Is it someone with the same experience or someone with a difference perspective? Do you need help with industry-specific skills or advice on broader issues like organisation or confidence.
• Do your research. LinkedIn, Twitter and business pages are all excellent places to find out more about potential mentors.
• Think long and hard about why this person would make a good mentor for you.
• Don’t ask for too much. If you don’t already know them well, suggest a coffee to see if you get on and are on the same page.
• If they are, bite the bullet; asking an inspiring woman out is terrifying, but chances are, if she’s as inspiring as you think she is, she’ll responded honestly and kindly. 

How to reach out to a mentor via email

• Keep it short – they don’t need your life story at this point
• Take it step by step – In the first instance, tell them you’re looking for a mentor and would they be open for a no-strings attached initial coffee?
• If you’ve already made initial contact, be bold: “I’m looking for a mentor to meet every six to eight weeks to chat through issues I’m having with my job and I think your advice could be invaluable. Would this be something you would consider?”
• In a couple of concise sentences, let them know why you’ve picked them. Is it their experience, their contacts, are you a fan of their work?
• Be accommodating and meet them on their terms. Perhaps a brief chat over Skype is easier for your first meeting? Show that you’re willing to do whatever they might need.
• Be gracious. They don’t owe you anything. A sentence explaining that you understand this might be something they want to, or can, take on is a good way to finish.

This piece was originally published in September 2019

Images: Getty, Toa Heftiba on Unsplash