You Don’t Have to Pivot Just Because the Pretty People on the Internet Tell You

Back in April, Allbirds made lots of headlines for pivoting from sustainable shoes to AI, which is pretty much the opposite of sustainable. I won’t miss them; I prefer shoes with support, stability, and no army of tech bros behind them.

Like any halfway decent Th0u9ht LeaDer *and* self-proclaimed small business owner, though, I couldn’t help but look at the reaction to the Allbirds news and think about what it means to honestly, actually, and meaningfully pivot. It’s an inevitable dilemma for just about everyone in the working world: Do I stay where I am, and risk becoming less relevant, or risk leaving behind what I know for something less familiar but potentially more lucrative?

The dilemma is especially acute when you’re a writer. The ol’ algorithms serve up all kinds of content aiming to convince you become a strategist, launch a podcast, or start a newsletter. If you’re independent, you’ll see advice to go in-house; if you have a corporate gig, the world will try to convince you to go solo. One post will tell you to become a generalist; another will suggest you find your niche. Oodles of people will offer unsolicited advice on using AI to automate all kinds of stuff so you can (presumably) spend less time working and more time sipping drinks in Cabo.

Your pal Beastwood isn’t here to tell you what to do. I’m just going to tell you to think long and hard about what you want to do and how you want to do it – and shut out all the noisy distractions.

Mistakes? I’ve made a few.

I say this because I have a good history of professional pivots that, um, well, uh, leave Current Me wondering that the hell Past Me was thinking. (Some of you who have known me long enough were probably wondering, too…)

• In the summer of 2000, lured by a classified ad promising $18 an hour (plus commission), I took two days off from my job at the local supermarket to get a crash course in selling knives door to door. Even if you only know me through my writing and haven’t met me in person, you can probably guess how hilariously bad I would have been at this. (It’s OK to laugh. I am, too.)
• At TechTarget, bored by .NET application development, I moved to the company’s fledging Enterprise Software group, the publisher of which had ambitions for dozens of complementary sites. The group and its exceptional burn rate folded within a few months. Luckily, one of the verticals had been in healthcare, and I was able to move over to the not-yet-launched SearchHealthIT.com. (That at least worked out in the long run.)
• In 2012, I left TechTarget for CIO.com so I could get “senior” in my title. But I missed covering healthcare fulltime, so in late 2014 I left for Fierce Health. There, I quickly remembered why I’d left the daily news business a decade ago, and less than eight months later I landed at Chilmark Research.
• Though Chilmark was serving me well, the company was struggling to grow. I pondered additional steps and landed on joining an agency, as it would round out a resume that included stints as a journalist and analyst, and who wouldn’t like such a well-rounded resume? Shortly after joining, I pondered why I thought that was a good idea.
• I left the agency for World Congress in June 2019, thinking that conference production would make use of my expertise, somehow be better than agency work, and make the resume even rounder. (More circular? Who knows?) It wasn’t. In this case at least, the pandemic forcing the company to lay off everyone who wasn’t a VP was a professional blessing in disguise.

TL;DR I bounced around a few times and learned the hard way that I didn’t want to do before I managed to figure out 1) what I did want to do and 2) how to actually succeed in doing it.

Too much pivoting = spinning in a circle

As I tell my 5-year-old whenever he doesn’t get something quite right, it’s OK to make mistakes. (For my purposes here, I mean mistakes like “took a job because it gave me a 15% raise even if the CEO gave me weird vibes” or “took a job so I could leave a company behind even though I didn’t love the new opportunity” and not, like, “forgot to put out the fire at the campsite.”)

I believe it’s also OK if you don’t learn from those mistakes right away – provided, again, that no one’s in harm’s way because of it. It takes time to figure out what you want to be when you grow up. Especially in Today’s World, the first job you take isn’t going to be your last, and no employer worth their salt should be the least bit surprised if a worker wants to leave for greener pastures.

Eventually, though, you need to reach a point where there’s a method to the madness of your pivots. Want a managerial role? Want to move into an adjacent vertical? Want more money? Want to live in Europe? Want different projects? They’re all perfectly reasonable motivations taking a new job, or a new client – but you should be able to explain why you’re making that move. Otherwise, you’re not pivoting; you’re spinning in a circle.

And – because, yes, I am in fact tying these points together – you understand why you’re making the move by learning from your mistakes. I’ve learned the topics I’m suited to cover, the varieties of products I like to work on, the types of clients I prefer and – critically for me – how much structure I need to have in place if I’m going to do something new. I can stray a bit off topic, or create written content in unfamiliar, if a client has given me good guardrails; otherwise, experience has taught me I’m not going to do so well.

Sorry, not interested

I’ve learned the hard way that there are a few professional pivots I’m not interesting in pursuing.

• Content strategy. I strongly prefer working with people who can tell me what they want.(What they really, really want, in fact.) I’m a sandwich-generation caregiver for my son and my mother, both of whom happen to be at opposing developmental stages where it’s often frustratingly difficult to communicate with them. I don’t need work to be the same way.
• Straight-up marketing. I know web copy, email campaigns, and social media posts are vital for many digital health brands. I’ve also found a lot of this work is below my pay grade, especially if clients plan to pay an hourly rate. This is one of those areas where I turn to my network for referrals so at least I’m not just saying “No” and moving on.
• Standalone proofreading projects. Same as above – the juice isn’t worth the squeeze given what these projects tend to pay, especially if I have to get onboarded and do cybersecurity training and fill out six forms to get paid. (If it aligns with topics I know well, though, I’ll consider it for existing clients.)
• Very niche topics. There are a handful of elements of enterprise tech, drug development, and healthcare operations that make absolutely no sense to me no matter how many times I try to figure them out. I’ve let myself – and my clients – down enough times to know not to bark up that tree any more. Again, I’ll put some feelers out to my network in these cases.
• A paid newsletter. The mediocre middle-aged white man confidence bouncing around my head tells me I could probably do this. The Principal and Co-Founder of my one-man LLC says it’s not worth it. I tend to agree with him: I just can’t foresee the payoff being worth all the work that would require. (Also, have you seen who has newsletters on Substack, or what the beehiiv founder’s been posting about? I have no interest in being even remotely associated with that.)

If you pivot, you should have a reason

I present that list of Stuff Brian Doesn’t Wanna Do because each item has something in common. If you spend enough time aimlessly scrolling, you’ll inevitably come across accounts (whether they are in fact people is partially in doubt) suggesting those are the things you should do to build your business.

I’m here to tell you that you don’t have to if you don’t want to. In fact, you should resist the temptation to pivot just because voices on the Internet say you should. Remember the lure of $18 an hour plus commission to sell knives door to door? It wasn’t worth it. Hell, it was probably a pyramid scheme. I was better off without it.

That brings me to a broader point: Nobody telling you that you simply must pivot has your best interests in mind. They want to sell you something.

I don’t mean, like, one eBook, publication list, or professional membership that will pay for itself as soon as a pitch is accepted, a project is assigned, or even a new connection is made. I mean those courses that give off the vibes of timeshare presentations and self-help seminars rolled into one – without the allure of free food (since they’re undoubtedly virtual for your viewing pleasure). Those resources that never quite give you the information you want, either because they’re so basic you already knew it all or the really good stuff costs five times more.

Look, I’m a privileged white guy. It’s easy for me to say “keep doing the work you like and pass on the stuff you don’t like.” My family will still eat if I say “No” to something that sounds lucrative but puts me too far out of my comfort zone.

But I also think I can say the seemingly aimless wandering of my career has taught me that pivoting for the sake of pivoting usually doesn’t work out the way you want it to. If you have good reasons, and you’ve thought about it, and you have a plan of action, it’ll probably work. But if you just want change – because you’re bored, external influences seem to suggest you should, or no one wants your eco-friendly shoes – it’s worth thinking about what’s truly behind those feelings and whether smaller, different steps can satisfy those motivations.