On October 27, 2014, a friend of mine tweeted a general question: If you could spend 24 hours in someone else’s job, who/what would you choose? I was brand new to the podcasting industry and in the honeymoon stage with my new side hustle, so I replied, I would love to be a full time podcaster. I’d take @DanBenjamin or @JesseThorn’s job in a heartbeat.
For those who aren’t podcast addicts, those men run two of the most successful podcast networks in the country: 5by5 and Maximum Fun, respectively. Their companies put out the majority of what I listen to. They’re self-made and quite successful – which is why it was such a shock for Dan to reply with ‘Let’s do that show this week!‘
Within a week or so, we had recorded a podcast episode together. It skyrocketed our listenership, and I was over the moon – but it didn’t end there. On November 22nd, I received a message from Dan asking When should we talk about 5by5? On November 25th, I received another: Today. This morning.
Around 8am, two and a half months after my podcast began, Dan offered the opportunity for my show to join his network, 5by5. I very enthusiastically accepted.
Obviously you don’t establish these connections as the result of a single tweet – but they can be made over the course of several, if you’re lucky. At the very least, you can get to know fascinating people, ask their advice, and perhaps gain a mentor along the way.
Of course we have to go back to the beginning, before I ever cozied up to a microphone. I was 26 and overripe for a quarter-life-crisis. I was in my second year of an office job that paid me well, but didn’t provide me much in the way of fulfillment. I wasn’t putting my Creative Writing degree to use, and, apart from reading ravenously over the spring and summer, I felt disconnected from creativity.
I was in luck, though. In the same time period, a friend (now my co-host) approached me with a proposition: starting a podcast for twenty-somethings. I said yes immediately – such a podcast didn’t exist yet, and I was a podcast junkie aching for a new pursuit.
However, it turned out that making your own podcast is not the same as listening to them, even an excessive amount of them. I could recognize quality when I heard it, but I didn’t know anything about mic technique, building an audience, promoting episodes, or making money. I was basically starting from scratch. Perhaps being a fan of industry leaders does not qualify you to be one; however, it does give you a jumping off point – knowing who to contact for advice.
Email requires perfect length and tone. Facebook messages are far too intimate for someone you’ve never met, and calling an office can lead to run-around or, at best, phone tag.
The solution is simple: Twitter. Twitter levels the playing field. You can reach out to whoever you want, up to and including potential mentors.
It may seem strange and nerve-wracking to tweet a stranger and ask for advice, especially if these strangers are at the top of your career field. You may worry that you come across as ignorant, or worse – a weird fan. You may not even know what to ask.
Luckily, the first tweet you have to send isn’t a question at all. You just have to start interacting. Once you’ve figured out who to approach, start small. This is about building a casual rapport. If they tweet something interesting, tell them so. If they tweet something that invites conversation, throw your voice in the ring. Connect gradually, until they begin to favorite your tweets, retweet you, or, in the best-case scenario, tweet you back.
At that point, you’re on their radar, and in the clear to ask for advice – but only advice. Asking for a leg-up in the industry is a turn-off, and ultimately unhelpful. You don’t want a shortcut; you want to know what they know so you can succeed as they have.
Start broad. Pick an area of your field, and ask something simple: Hey [career idol], what do I need to know about _________? It’s an excellent opener because it’s an innocuous question. It can elicit any kind of response: long or short, simple or complex. It also allows for you to ask follow-up questions if the tone of their response invites them.
Now, you’ve essentially established a casual rapport with your initial question, so the advice-ice has officially been broken. However, that cannot be your only interaction (if that’s not immediately obvious). You should want to interact with this person both casually and professionally and they want to know that you’re not simply using them for their advice.
From there your relationship will naturally build, stagnate, or fade – you have to be prepared for any of these outcomes, as they’re all ultimately positive. If you truly relate, fantastic! But if you don’t, follow the old maxim and try-try-again. If it ultimately fades, then perhaps it simply was not meant to be a connection and that’s okay. A mindful connection is just as important as quality advice when it comes to mentorship.
The first person you speak to may not be the one for you – like dating, finding your mentor can take time. But with a tool like Twitter at your disposal, it’s all the easier to recognize someone with diverging interests, leaving you free to find, speak to, and interact with someone who clicks. After all, that’s what true mentorship is built on.