Part VII - How to level up your Weird Internet Career

Previously: Is it too late for me to start my Weird Internet Career?

So, you make weird things on the internet. People like them. Maybe they pay for them sometimes. You might have the beginnings of a Weird Internet Career. But you’re trying to figure out how to make it really sustainable.

Getting a mentor

Even though all Weird Internet Careers are different, there are often people who are a notch or two ahead of you on a similar-enough trajectory that you think, dang, I bet this person knows what I should be doing next. But if you’re not in a traditional workplace hierarchy, they’re not going to get assigned to mentor you. And one does not, generally, get a mentor by asking someone “how do I become you?” or even “will you be my mentor?”

Instead, the effective mentoring question is, “I’ve done X and Y towards Concrete Goal, do you have any suggestions for what I should do next?”

This is a much easier question to answer, and many people are willing to do so if you ask it in a setting where they have time and are in a social mood, especially when you have genuinely already taken some steps towards that goal. How do you know which first steps to take without a mentor? My suggestions are google, following your would-be mentors for a while on social media, and looking through their website/archives for anything that might be relevant (such as what they were doing when they were at your earlier stage).

Sometimes you can accomplish this part somewhat accidentally by making things in public which cross the path of someone a step or two ahead of you and make them say “have you ever considered doing X?” when you happen to be in conversation — or at least make them able to answer your less focussed mentoring question in a way that’s still useful to you. That’s a good reason to be making things in public, but it does still rely a bit on luck, so it’s never a bad idea to actually point out what concrete things you’ve already done. Even if your concrete step is “I read all your posts about X and Y, and I’m still wondering about Z”, this at least shows some initiative. (Though actually having tried something from the posts is better.)

The next step is equally crucial. Often, the would-be mentor will give you a very concrete suggestion. Sometimes it is just strongly encouraging you to do the thing you already mentioned: Yes, you should write that blog post. Yes, you should make a professional website. Yes, you should write that book proposal. Sometimes it is a concrete thing that hadn’t occurred to you: Pitch something to this place. Make an email mailing list. Read this book or that blog. Send me an email with certain info. (At this point, saying “that’s great advice, let me write it down” wouldn’t be taken amiss.) 

There’s a loop that’s easy to get stuck in where it’s more fun to consume productivity advice, read endless posts comparing systems, buy snazzy crisp notebooks, etc than it is to actually do the things the advice is telling you. Doing things is scary! Then people might look at your thing! Then people might not look at your thing! What if they don’t like it? What if they like it too much and you can never do anything else that measures up? What if it’s not good enough to show this person you admire? What if it’s not the perfect version that’s inside your head? Doing things is hard. And. Doing things is necessary. Your would-be mentor knows this — after all, you wanted this person to mentor you because of things you’ve seen them do. If you want to get to the point where one day you too get to give young grasshoppers the advice you wish you’d gotten, the path there is through doing things. 

In any case, you should go do the thing and then report back to the advice giver with how it went. This crucially shows that you’re a person who’s worth giving advice to and not someone who’s all talk and no action, so now it’s worth them giving you more advice and maybe even sending opportunities your way. Any time you write down advice, also write down the name of the person giving it to you so you remember who to follow up with. Don’t skip out on the reporting step, even if some time has gone by or it didn’t quite go as planned or you’re not sure about how good your thing is. Make a good-faith effort to do the thing; report back on how it went. Voila, you’ve now completed one mentorship cycle!

People sometimes don’t report back because they’re worried about annoying a person they admire. This is valid, but untrue: reporting back is actually providing emotional gratification. The report back is the absolute best part. Advice-givers love to feel like it was actually worth it rather than throwing their advice down a bottomless pit. Don’t bother them with excuses about not having done the thing, but even if it’s been a year or two later, a brief “I know it’s been a while, but I wanted to say that I took your suggestion to do Thing and…” is a delightful message to receive. I’ve even done “hey, just wanted to say that I’ve passed on that advice you gave me many years ago about X to another person/several other people since then and it’s been super helpful to them too”. Now your mentor is a grand-mentor! People love this! 

If you’re still nervous about reporting back my recommendation is to report back in a very no-strings-attached sort of way without making further requests. You might or might not ask them for advice again at some point in the future, but either way they think of you with a positive memory as “that person who sent me a lovely thank-you message after they took my very good advice” rather than “that person who I gave a bunch of advice to but who knows if they ever did anything with it.”

Or, if they’re a very busy person who freely dispenses advice to a lot of people, they may not even remember that they gave you advice! In that case, reporting back is also a great way to remind them who you are. Trust me, I am one of these busy people, I promise this post is not a massive subtweet if I’ve ever given you advice because I’ve probably forgotten about it and I know life happens sometimes, but I do remember the much fewer number of people who report back.

Let’s put it this way: like how a prof can’t just show up at your house if you’re a student (you have to go to office hours), it would be pretty awkward for an advice-giver to message you checking in on how the advice went, unless they’re in a formal role like an advisor or boss, or they (maybe) happen to run into you socially. They don’t want to embarrass you if you haven’t gotten around to the advice yet, but everyone likes being thanked! That’s why you need to bring it up instead. (But profs also like it if you check the syllabus and try getting notes from a classmate rather than showing up to office hours after skipping class all term and asking “what do I need to know for the exam?” That’s asking for mentorship before putting in any concrete steps yourself.)

I’ve done this mentorship cycle on both the mentor and mentee ends many times, and the ones that work out to be really satisfying follow this pattern: give advice, take advice, report back. If they gave you several concrete suggestions the first time (lucky you!), you can report back after just one or two, but in that case don’t ask for further advice until you’ve tried most if not all of the suggestions they’ve already given you. You might not even need to ask for further advice, if you find that awkward! Sometimes the mentor will be so pleased at simply seeing the results that they’ll just offer advice on next steps spontaneously.

People often love the idea of mentorship more than the execution part of actually taking the mentor’s advice. But if you want to be able to ask this person for advice or help again in the future, you need to actually try doing the advice they’re giving you now. Even if it’s a really tiny piece of advice. Especially if it’s a really tiny piece of advice. People like feeling like they’re investing in someone who’s going to do them proud; people don’t like the feeling of throwing good money after bad (in this case, more advice after untaken advice). If you don’t feel like you can take this person’s advice, then that might be a sign that actually they’re not a great mentoring fit for you right now, which is also a useful thing to learn (or it might be a sign that you need to get your act in gear).

If you tried the advice and it doesn’t go that well, or you ran into unforeseen complications, those might be a thing that a mentor can help you with! But neither you nor they will know about how they could help if you don’t give the thing a solid try first and then report back once you’ve made an effort and gotten stuck. 

This might sound like a lot of complex steps if you’re thinking about it for the first time, but I’m writing it down very explicitly because I think that mentorship norms are often part of a “hidden curriculum” and I want to especially encourage people who don’t have access to this tacit knowledge to develop satisfying mentorships too.

I sometimes talk with people who say they haven’t had any mentors, or had very few, or don’t know how to find a mentor. And maybe it’s the case that I’ve been unusually fortunate in the mentorship department. But I also think our culture doesn’t do a great job in training people to spot the mentorship dynamics that are all around us. In fiction, mentorship is often very formalized: you climb a mountain in search of a teacher who will be Officially Your Mentor for a defined span of years in which you work with them every day. 

In real life, I’ve found that mentorship dynamics can be more fluid: sometimes I participate in several rounds of advice/trial/report before either of us calls it a mentoring relationship, if at all. Sometimes it’s only years later that I realize that hey, this person whose advice I’ve never forgotten could actually be considered a mentor (or that my support was more impactful on someone than I realized at the time). Sometimes it’s only a single piece of advice that happens to hit at the right time. Sometimes it’s less a concrete piece of advice and more of an approach to living that can be intertwined with a friendship. Sometimes I’m mentoring someone on one plane of life while they’re mentoring me on another. Sometimes a mentor also overlaps with a formal guidance role like a teacher or editor; sometimes a mentor is a person who fills in the cracks when people in formal guidance roles are lacking or overwhelmed. 

It’s easy to wish for exactly one person who’d just tell you exactly the steps you need to take in order to have a satisfied life, and then hold your hand as you do them. Easy and, alas, not how the human condition works. (Though there are jobs that will provide a much more defined achievement scale, if that appeals to you. I suspect, if you’re this far into reading about Weird Internet Careers, it may not.) Ultimately, you’re the one who needs to cobble together the various sources of advice available to you and figure out how to make from them something you can live with.   

Looking for advice

You don’t necessarily have to ask for mentorship explicitly. Many people who are a step or two ahead of you even put their advice out on the internet for free. (I’ve written several previous advice posts about communicating linguistics and other complex topics. And while writing this series, I realized that I’d been getting many requests for advice about how to publish a book since mine came out, so I added some links on book advice to my FAQ.) Because every Weird Internet Career is so different, one of the essential skills of building one (especially for the Weirdest Internet Careers which can’t even be named after a specific platform) is looking at other Weird Internet Careers and figuring out how their strategies might or might not apply to yours.

In building my Weird Internet Career as a pop linguist, I’ve read advice from a lot of different corners. I read advice about my specific niches, including podcasting, writing practice, freelance writing, being an author, book publishing, science communication, public speaking, Patreon, and general business advice, including notably Get Bullish and Stacking the Bricks. Sometimes random applicable stuff just pops up, like this thread about blogging as a Weird Internet Career, this podcast about influencers as a small business, this video which mentions systematically watching through the back catalogue of other youtubers (a useful tip for other genres as well), or this thread about writing nonfiction books as a small business (note the part about it taking 5-10 years to get a small business off the ground, which I agree with. I’m in year 8). I also get to have interesting meta conversations with fellow people who also have Weird Internet Careers (especially at XOXO, which is basically an entire conference for people around the artsy/techy subset of Weird Internet Career), trading tips about what’s working and what’s not working, especially in recent years as I’ve had increased visibility.

For fellow Weird Internet Career people, I’m hoping to expand the conversations that I often see happening within particular silos, such as podcasters or writers or people who use a particular platform. Because there’s really no one else so far fully at the intersection of “Weird Internet Career for pop linguistics”, I’ve had to seek inspiration more broadly, but I think this would be useful for other domains as well. For example, from more businessy-focused advice I’ve learned about making clear the value that you’re providing to people who are paying for your thing, whereas from the artsier side I’ve gotten a lot of useful tips about the practical aspects of motivating yourself to keep making things incrementally even when you’re not seeing immediate results, through structures like NaNoWriMo, 100 day projects, shitty first drafts, and the Helsinki Bus Station Theory.

For linguists, I think there’s definitely space for more linguists to do the specific things I’m doing or other types of lingcomm (I want more good short-form pop linguistics writing! I want more pop linguistics books by actual linguists! I want more great linguistics stuff in other media! I also think other people want more of this than I, just one person, can provide). There are indeed other linguists doing things in many of these areas, and I’ve posted advice before about writing pop linguistics articles or about “Linguistics + X” (combining linguistics plus some other area of interest to put yourself in an interesting niche). But what I haven’t seen as much is an awareness of how to build pop linguistics into a sustainable career via the internet, even if all your income isn’t coming from just one thing (especially if all your income isn’t coming from just one thing). So I hope that this encouragement to look around to Weird Internet Careers in other domains for inspiration is helpful.

For both mentorship and general Weird Internet Career founding, the first step is actually doing something that people can be a fan of. So much of that early “testing” sort of mentorship advice is just actually make the thing and put it online. Write blog posts. Write an email newsletter. Make a podcast. Make videos. Make them helpful or interesting. Notice what’s working or not working, what you like or dislike about related things in other genres. Keep doing it regularly. Your first ones won’t do that well, but keep building a consistent track record.

In short, if you want people to think you’re an interesting person who’s worth connecting with interesting opportunities, you need to actually make things and put them out there. No one knows how interesting you are if you keep your interestingness inside your head. Referrals only go so far: I can’t make other people become a fan of you if you’re not making anything for them to be a fan of.

In my opinion, the very best part about having a Weird Internet Career is how putting so much of your work out in public leads to meeting really interesting people who are also talking about their work. If you’ve never had a friendship founded on mutual admiration for each other’s work before, please allow me to take this opportunity to strongly endorse it.

I don’t have a magical set of steps. But what I’ve noticed is that, with a lot of unglamorous steps, sometimes you can create your own magic.

I’m posting this series about Weird Internet Careers and how to build them to my blog over the next few weeks. However, if you want to get the whole series now as a single doc, with bonus Weird Internet Career-building questions to think about, you can sign up for my newsletter on Substack here, which will also get you monthly updates about my future Weird Internet Career activities as an Internet Linguist.

Part I - What is a Weird Internet Career?
Part II - How I Built a Weird Internet Career as an Internet Linguist
Part III - How to start a Weird Internet Career
Part IV - How to make money doing a Weird Internet Career
Part V - What can a Weird Internet Career look like?
Part VI - Is it too late for me to start my Weird Internet Career?
Part VII - How to level up your Weird Internet Career