The Beastwood Files: September 2026

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Just when I thought I’d return to some semblance of a normal schedule, my mother fell twice in the span of about 10 days and, amid a one-week stint in rehab, the family decided the time had ultimately come for her to move to assisted living. While she’s warming to the idea, her cat – who’s been alone in her old apartment for the better part of a month – isn’t quite ready yet, alternating between hiding in the closet and hissing at me when I try to say hello. Oh, and we need to move her for the second time in 18 months. This pic of my son with the playmat on top of his head pretty much sums up how I’ve been feeling at the end of these long days.

Stuff I Wrote

Things I Did

  • Drop down from the full marathon to the half marathon a month from now with no regrets
  • Wait until it was 40-something degrees at 8 a.m. to finally wear long pants to kindergarten dropoff
  • Regret the decision to switch to long pants when it was 80 degrees a couple days later
  • Not yet determine when the family will go apple picking this fall, which as everyone knows is a prerequisite for being allowed to live in New England
  • Not scold our cat for getting on the kitchen counter, since she turned 18 a month ago and frankly I’m more impressed that she can still jump that high than mad that she might get into something

Adventures in Fatherhood

  • Basement LEGO FTW. We were throwing a tantrum the other day because we wanted to peruse the selection of sets of small interchangeable plastic bricks at a local toy store we just happened to be parked one block away from. I managed to squelch the tantrum by remembering that I’d procured a sizable holiday LEGO set for myself in like 2023, subsequently left it in a bin in the basement, and delivering on my promise that said set would be cooler than anything we’d see in the store. Three-plus hours (and perhaps a delayed bedtime) later, we’d completed Holiday Main Street.
  • This summer, we established that Daddy’s grad thesis – a 170-page tome on Great Britain’s first, failed application to join the European Economic Community – is dreadfully boring. This summer, we also learned a song for preschool graduation that kicked off with the line, “We’re going up, up, up to kindergarten.” (It’s apparently sung to the tune of Something the Kids Are Into These Days.) Recently, we’ve put these things together in a delightful little song: “We’re going up, up, up to graduate school / Gonna write a thesis that nobody reads.” My wife even made up a dance.

Happy fall, happy Halloween, happy near-end to Daylight Savings Time, etc.

Working With Freelancers? You’d Better Have a Plan – and Be Ready to Talk

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Since branching out from journalism and market research nearly a decade ago, I’ve worked with a lot of clients (and clients’ clients) in a content role. These companies have operated in several healthcare and technology market segments, and they’ve ranged in size from startups to multinationals, but many have had one thing in common.

Sometimes it happens almost immediately, and sometimes it takes several months. But nearly every time, the conversation shifts from “We’d love to have you on board to do foundational long-form content!” to “Hey, can you write a press release?” or “Hey, have you ever written web copy?” (Or, in the case of where I worked full-time for all of 8 months, “Hey, can you copy edit a PowerPoint our client’s using for an internal meeting?”) In most cases, this shift follows a period when my workload has been lighter than expected, whether explicitly stated in my contract or generally agreed upon in principle.

Be honest about the workload you can offer

There are typically two factors at play in these situations. One is immediate, readily apparent, and fairly superficial: The client ran out of things for me to do. Throwing another project my way can certainly serve as a stopgap measure, and make me feel appreciated and wanted, but it tends to reflect the second, much more systemic, factor: The client never had enough things for me to do in the first place.

I’m generally sympathetic toward whomever the client has tasked with managing me, since the dried-up content pipeline usually falls on the shoulders of someone else. I’ll express frustration, but I’ll do it politely.

I’m less sympathetic to the clients themselves. Why would you enter a business agreement with a content person without a clear-cut plan for providing them with a steady stream of work that makes the most of their capabilities?

I’m not arrogant enough to think that every content meeting has an agenda item called “What to Assign to Beastwood, Our Amazing, Funny, and Handsome Content Guru,” but it’s not unreasonable to think that you’re at least occasionally talking internally about how to use the skills of the person you agreed to pay to do work for you on a regular basis.

If you don’t expect a regular cadence of work, that’s fine. Hire the writer to do your foundational content, pay them, and then call it a day. Or, hire them to do occasional work, with the understanding that they may not always be available because, well, you’re only asking them to work occasionally, and chances are they have other work from other clients who do give them regular assignments, and therefore plan for a project to take a few weeks to complete.

Both of these arrangements are perfectly reasonable. I’ve done single foundational pieces for more than one client, and we’ve both walked away after the piece was done, happy with what we’ve produced and knowing full well that would be the end of that. I’ve also worked with multiple clients who’ll reach out every few months with an assignment that’s not especially time sensitive. This work won’t win me a Pulitzer or pay for our overdue bathroom renovation, but it will add to my writing portfolio and After-School Snack Fund without leaving me frustrated or befuddled about a lack of follow-up.

Make a plan before making promises

Don’t promise a writer a regular cadence of work – a set number of hours per week, or a set number of pieces per quarter – without first knowing how you plan to get the writer that work and then sharing that plan with the writer. You need to be able to account for five things:

  • What you want.
  • When you want it.
  • What you can pay for it.
  • Who you’re relying on (mostly internally, but occasionally externally) to get the writer what’s needed to get it done.
  • What will hold it up, whether it’s a release date that may not actually happen or a team of executives arguing in Microsoft Word comments whether a solution synergizes data or leverages it.

At best, without a plan you’re flying by the seat of your pants trying to keep a writer busy, and you’re not meeting the expectations set forth in your contract. At worst, you’re leaving a writer on standby, telling them that work is coming at some point, probably soon, but maybe later – and giving them all the more reason to look for clients that don’t promise something they can’t deliver. (And, if you have the person on retainer, you’re probably lighting some money on fire, too.)

Don’t be afraid to talk about it

Here’s another way to think about it. That freelance writer is essentially a business partner. Odds are they’ve created an LLC, or at the very least a DBA and business checking account. They probably have an accountant and calculate business expenses (even if they’re primarily Post-It notes, newsletter subscriptions, and reams of printer paper that may or may not also feed their child’s crafting supplies).

Does your company leave its traditional business parters guessing, or do you routinely check in with vendors and consultants? When things start to get light, do you forget about them, or do you work together to come up with ways to get more done, in accordance with their skills and your shared expectations?

There are plenty of reasons for a content pipeline to dry up. I get that nearly all of them are beyond your control when you’re one cog in the corporate machine. But if you want to build longstanding relationships with freelancers – who will remember you when you take on a new role and, on the other hand, won’t be afraid to spill the tea if things fizzle out – then it pays to treat them as partners.

That means having a coherent plan for how you intend to work together, along with having difficult conversations when that plan starts to fall apart. The sooner you open those lines of communication, the more likely you are to avoid the awkwardness of explaining to them (not to mention your boss, and probably the people who make your budget) why there’s nothing for them to do. You’re also more likely to salvage the situation without having to tell a freelancer they can’t work with you any more because you ran out of money or capacity – or having the freelancer walk away because they’re smart enough to see the writing on the wall.

This Summer in Digital Health: Now With 78% More Original Thoughts!

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Welcome to This, er, Summer in Digital Health. We’re going to pretend I took the summer off from highlighting key headlines in healthcare technology and why they matter because I was busy peering off into the distance contemplating the right format to better engage with my readers and not because the least stressful way for the Beastwoods to navigate the transition from preschool to summer camp to summer vacation to kindergarten was for me to work quite a bit less.

Anyway … welcome to my new newsletter format! There’s still a handful of key themes, though there will probably be fewer than I’ve featured in the past. What’s new? More insights straight from my brain! When lots of headlines drop on the same topic, it’s easy to miss the forest for the trees. Here’s to hoping my perspective / free time to actually sit with these stories helps you make better sense of it all.

Does healthcare fear AI is too risky for clinical care?

If the first few months of 2026 were about the promise of AI for clinical care, as seemingly every tech company released an AI agent to automate this and streamline that, the headlines this summer seemed to suggest the honeymoon period is over.

My take: AI for clinical care is starting to seem a lot like coffee. One day, it’s bad for you. The next day, it’s good. The next day, it’s still good, but only in excessive quantities that make you jittery, paranoid, and irregular. Organizations clearly know they need to erect guardrails and draft governance policies, but FOMO seems to get in the way of taking these pragmatic and logical but also time-consuming steps. Unfortunately, that inaction is going to bite them back. I wouldn’t be surprised if the majority of pilots die on the vines in the next several months, along with the companies that created them.

With wearable data, everything old is new again

This summer, both Apple and Google announced updates to the health, fitness, and safety features linked to their watches and wearables. Meanwhile, a recent AMA survey found that most physicians do in fact review wearable data, 77% find it valuable for clinical care, and close to 30% have acted on the data they saw – findings that even surprised the association’s CEO.

However, only 6% have been able to integrate wearable data with clinical workflows. On top of that, many physicians don’t really trust wearable data, especially if it comes from FDA-cleared and not FDA-approved devices. Plus, few bother to use diagnostic and billing codes for remote monitoring, which would be the main motivation to look at and act upon wearable (or sensor) data in the first place.

My take: The challenge of figuring out what clinical teams are supposed to do with heaps of consumer wearable data is a tale as old as time. The evolution of technology over the last couple decades – from spreadsheets to databases to dashboards to generative AI summaries – clearly hasn’t made things any easier. As with a lot of healthcare’s problems, this one would have been solved by now if stakeholders wanted it to be. Since there’s no incentive for providers to even look at data, let alone interpret it and incorporate it into care plans, it’s just going to sit there, largely ignored, as it always has been.

Digital health apps benefit some conditions more than others

A literature review in The Lancet found that digital health apps work well for managing many conditions and symptoms – namely blood pressure, blood glucose, mental health, body weight, physical activity, and medication adherence – but not everything. Managing cholesterol, body fat, heart disease, and healthy diets proved to be difficult with apps alone, as these areas often require clinical inventions in addition to the educational content, feedback, and support loops that apps tend to specialize in.

My take: A lot of healthcare research confirms things we already knew, or at least suspected to be true. While this paper fits that description, that’s not necessarily a bad thing. Given the industry’s incessant push to do more with less, particularly when it comes to engaging with patients using technology that never quite lives up to its ROI potential, it’s helpful to have clear evidence of which apps can stand alone and which apps would need an all-important human touch and, depending on who, you ask, may not provide enough juice to be worth the squeeze.

The Epic effect remains strong but shows some cracks

Research firm Redesign Health published a report on the Epic Effect, or the strong gravitational pull of the industry’s leading technology vendor. More than 70% of health systems surveyed described themselves as Epic-first, and more than 90% are confident the vendor can execute on its AI roadmap. That said, nearly two-thirds would buy from a startup if it did something Epic doesn’t do as well, such as imaging, quality reporting, and scheduling and discharge. Also, 48% of health system admit they select Epic because it’s “good enough,” which the consultancy said suggests that “Epic gets to clear a lower bar.”

My take: Winston Churchill is credited with saying that democracy is the worst form of government except for all the other ones. Healthcare seems to feel the same way about Epic. Keynote speakers and other thought leaders are quick to offer criticism – some of it warranted, given its history of integration frustration and recent antitrust allegations – yet the company’s market share is only going up. Yes, there are sunk costs associated with keeping your current EHR, and it sure helps when the same vendor offers integrated features that meet needs you didn’t realize you had. At the same time, let’s remember that Judy founded Epic in 1979 (the year before I was born, mind you). That means the industry has had almost five decades to build a better alternative.

Bulking up build efforts in the build vs. buy debate

A couple publications offered new takes on the omnipresent build vs. buy question for healthcare’s technology teams. Healthcare Dive unpacked the effort to build oncology patient management tools at NYU Langone Health and Dana-Farber Cancer Institute, and Digital Health Insights explained the Cedars-Sinai approach to engage stakeholders from the beginning to ensure efforts succeed. That engagement helps avoid the pilot purgatory problem that plagues innovation efforts viewed less as tried-and-true technology implementations and more as experiments; it also helps demonstrate to decision-makers that teams know what they’re doing and deserve some leeway to tinker if they have a good idea.

My take: It’s interesting to see this topic continually resurface, as it’s a tale almost as old as time. For general-purpose technology, or anything that needs to be done at scale, Buy is a pretty clear answer – or Partner, if a health system is large enough to meaningfully influence what a technology vendor will do. Build makes more sense for anything highly specialized and/or personalized, either because the patient (sub)population is unique or the process is nuanced (a polite way to say complicated). Yes, AI is moving the needle on scaling specialized, personalized, and nuanced workflows enough to shift some technology from Build into Partner or Buy, but systems still need to weigh how much control over the process they’re willing to give up for what very well may be the temporary convenience of not doing it themselves.

Digital health funding trends don’t shock or surprise

The latest analysis of digital health funding from Rock Health found that deals are getting a little bit bigger, while deals more than $100 million make up an increasing volume of all capital invested. The firm found that investors prioritize domain expertise, scalability, post-implementation support (especially when it comes to AI), and broad partner ecosystems. Conversely, Modern Healthcare reported that investors shy away from point solutions, products that don’t scale, and business models solely reliant on reimbursement models subject to the whims of the Trump administration (my words).

My take: The points about which product categories aren’t seeing much investment make perfect sense and suggest the digital health landscape is maturing quite a bit. This also ties back to a couple of the other themes. If Epic is going all-in on AI, it stands to reason that AI startups will soon face a steep uphill battle and cannot rely on their products alone. If more health systems are comfortable rolling their own software, there’s less room for unfamiliar partners. Plus, just about everyone’s operating on razor-thin margins, and ROI is one of the first terms to come up in any conversation about technology investment. I get the feeling a slowdown is coming.

The Beastwood Files: August(ish) 2026

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We’ve officially started kindergarten, which means our schedule is (relatively) normal up in here. After roughly four months of juggling – I think I had five uninterrupted weeks of work between late May and early September – I almost have the working hours of a normal full-time employed person. Almost.

Stuff I Wrote

Things I Did

  • Navigated the transition from preschool to summer camp to vacation to kindergarten without my hair getting any more gray than it already was
  • Took our son on his first “hike” up a “mountain” (Flying Mountain in Acadia, elevation 284 feet) while surviving multiple outdoor potty breaks and mangled attempts at a downhill piggyback ride
  • Honored the cat’s 18th birthday by leaving her all alone in a quiet house for an entire week, interrupted only by a catsitter who ranks among the handful of people who can confirm she exists
  • Went to my second Red Sox game with my son, who said the best parts of the game were watching the tarp getting removed and participating in The Wave
  • Started decorating and acquiring candy for Halloween, even if we’ve yet to decide what we want to be

Adventures in Fatherhood

  • During Kindergarten Rumspringa – the week and a half bookending Labor Day when we had one day of school out of seven weekdays – we hit just about every museum and major tourist attraction that Boston has to offer. The Duck Tour was a favorite, we liked the View Boston gift shop more than the experience itself, and (as usual) nothing beat the Discovery Museum.
  • We’re now ranking supermarkets by the availability of Cool Shopping Carts. Stop & Shop and Trader Joe’s are boring, while Donelan’s (a small chain west of Boston) is not; depending on the location, there’s the option to sit in front of the car and use a steering wheel or – even better – a child-size shopping cart to push and fill on your own. Market Basket is a wild card: If we can find the carts with bench seating *and* have the patience to wait in line *and* Dad says we can get yet another novelty balloon, then it’s a win.
  • Thing I Learned the Hard Way: Don’t let your kid talk you into getting a fly swatter. We found one on a recent grocery store trip, and I allowed it since 1) it was 30 cents, 2) it’s practical, and 3) it was used for a preschool craft project. Now, though, I’m being pestered to print out sheets of paper with pictures of flies on them that we can “swat” with paint – and while I garner the courage and wherewithal to figure this out, we’re using the flyswatter to smack light switches. Not my best moment as a father.

Happy September. May you achieve the levels of cozy, pumpkin spice, flannel, and football that are right for you.

The Beastwood Files: July(ish) 2026

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This may be news to some of you, but apparently navigating the transition from preschool to kindergarten comes with Big Feelings that are hard to talk about but somehow seem to rear their ugly head at the exact moment that Mommy and Daddy are asking that you brush your teeth.

Said feelings, coupled with being the only child in the preschool class to have dropped a nap, led the Beastwoods to tweak the preschool schedule in our waning weeks. That has meant less time for me to devote to the lovely craft of writing and checking emails (the two tasks my son is convinced comprise the entirety of my job). I was kinda sorta prepared for this, professionally and financially if not necessarily emotionally, and have thus spent the bulk of the last few weeks juggling responsibilities, asking for extended deadlines, and wondering if I’ll ever to things on my to-do list like “organize the giant pile of papers on top of the filing cabinet. (Answer: No.)

It’s been A Lot, but it’s also been fun. We’ve taken some weekday trips to museums and playgrounds, had more time to spend at home in the morning (because free play time with 4-year-olds is No Longer Fun), and learned new things like how to make squiggly lines by typing non-words in Word. (Yes, I use Word. I will not be taking any questions at this time.) And, of course, my amazing mother in law has lent a hand. Through it all, I’ve learned how important it is to prioritize what matters – and how rarely that’s enterprise B2B content for healthcare.

Let’s get on with it.

Stuff I Wrote

Things I Did

  • Nailed the most important deadline of the month: Signing up for fall swim class sessions at the local Boys & Girls Club
  • Scheduled an appointment with my eye doctor, dentist, and PCP for the same week, which is good from an efficiency perspective but bad if you don’t want to feel old
  • Endured some of the sweatiest runs of my life in suffocating July humidity and reinforced that this is by far my least favorite season of the year
  • Somehow managed to help set up a campsite (complete with canopy) in 90-degree heat and humidity (with minimal grumbling from all parties involved) and further reinforced that this is by far my least favorite season of the year
  • Watched my son have a little bit too much fun setting marshmallows ablaze in a campfire
  • Get a new keyboard (and wireless mouse) after I got juuuust a little tired of my son (who’s been beginning to type) noting that the “A” key was faded on the old keyboard
  • Answered questions such as “Why do I still have to go to preschool?” “What will summer camp be like?” “Why do I have to go to kindergarten?” “How many days of preschool are left?” and “When are we going on vacation again?” roughly 56 times
  • Forget to take any photos worth sharing that don’t include my son’s face, which explains the hilariously awful image for this post

Happy August. The humidity’s finally breaking in the Boston area. Best luck with the first day of school for those with children. Best of luck with 5-day work weeks and actual deadlines for everyone else. Best of luck with Conference Season for everyone.

The Beastwood Files: June 2026

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Been a busy few weeks in the Beastwood house. My son survived his kindergarten screening and a trip to a new dentist, I survived three trips to the doctor (for routine appointments, thankfully) with my mother, and we all survived four and a half days in the White Mountains for the Fourth of July (a trip bookended by visits to two different children’s museums in southern New Hampshire).

Stuff I Wrote

Things I Did

  • Went to more beaches than I can count and didn’t bother to clean the trunk
  • Attended my son’s preschool graduation, complete with mini caps and gowns
  • Experienced the brick-and-mortar sociology experiment that is Walmart Supercenter in Conway, N.H. on the Thursday before Fourth of July weekend to buy as many box fans as I could fit in a single shopping cart to cool off our AC-less rental condo while the heat dome covered the East Coast
  • Signed up for the Manchester (N.H.) City Marathon with the hopes of avenging my Worst Marathon Ever, which I ran there in 2012 (through no fault of the race itself, which is actually quite lovely)
  • Learned that the easiest way to remove matted fur from a long-haired cat is, believe it or not, to gently pull it out

Adventures in Fatherhood

  • In the weeks leading up to Father’s Day, I joked with my family that, as a Boring Suburban Dad, all I wanted as a present was white socks. My son sensed that this was a Dad Joke and was all too happy to play along – and even told me a trip to CVS with Mom was happening so they could get *black* socks to go with them. (I also got to sleep in while Mom and son went to Dunk’s.)
  • When we talked about activities to plan for the Fourth of July in New Hampshire, my son said he wanted to make a gingerbread house. As astute readers will recall, we made a gingerbread house for St. Patrick’s Day, so this request wasn’t out of left field. My son has no interest in eating any of the candy with which on traditionally decorates a gingerbread house; it’s all about the experience. This experience meant red, white, and blue candy, of course.
  • Though our primary connection to the World Cup is themed Squishmallows acquired via Happy Meals, we did catch the end of the Brazil-Norway Round of 16 game while out to dinner on vacation. Amid explaining the intricacies of soccer to my son AND father-in-law (thankfully neither asked me what it means to be offside), we decided our favorite player is The Viking. I can’t really argue with that.

Happy rest of July. We’re home for most of the month, which means we’ll do approximately 2,345 extemporaneous craft projects. The crayons are ready…

This Month (or so) In Digital Health: AI, Data, GLP-1s, and Money (Lots and Lots of Money)

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Welcome to the eighth edition of This Month in Digital Health, where you get to read my very own thoughts on the news and trends that caught my attention over the last few weeks. We’re a bit tardy this month – Sandwich Generation Caregiving for the win, am I right? – which means there’s been extra time to gather hot takes on AI, data, healthcare costs, and GLP-1s. Have at it, folks.

AI likes it easy. Healthcare isn’t. Therein lies the rub. Yet another paper has shown that LLMs can outperform physicians when making rote decisions (even general-purpose LLMs) that don’t have to account for the stuff that happens in real life – whether it’s delays in prior authorization or claims denials powered by AI or, like, patients’ unaddressed social needs or the stress of the hospital. Nor does it help that providers fear overreliance on AI will diminish clinicians’ critical thinking capabilities.

Who can access data? What is data? What is access? Rock Health found that 57% of Americans own at least one wearable, and many are tracking health metrics. That’s good! The bad news: Wellness apps interpreting device data aren’t really regulated, and physicians have no idea how they conclude a patient is at risk of, say, depression. Plugging data into an LLM isn’t much better, as general-purpose LLMs aren’t HIPAA covered entities (though the healthcare-specific ones are).

GLP-1s are taking over healthcare, and not in the best ways. Speaking of wearables, Mass General and Samsung Health are partnering to see whether a smartwatch can track muscle loss in adults on a GLP-1. That’s good, because it’s a common concern for patients who lose weight. Other concerns are emerging, too, including GLP-1 prescriptions from telehealth providers who don’t talk about the risks or the importance of healthy habits, and the efficacy of GLP-1 pills, which has self-employed insurers thinking twice about insurance coverage.

Great googily moogily, healthcare is expensive. On top of everything else, GLP-1s are making healthcare even more expensive – to the tune of 9% increases in commercial costs in 2027, per PwC. Only 7 nonprofit Blues plans had positive operating margins in 2025, and many provider-sponsored health plans are giving up amid rising costs and general industry instability. Speaking of which, more than 75% of executives think healthcare’s financial instability will reach an existential tipping point before the end of the decade. Good times.

Meanwhile, in other stories of interest:

  • Given the odd juxtaposition of primary care (with low costs and generally stable utilization) and health insurance (which is meant to cover expensive, unpredictable events), a JAMA paper proposed the notion of primary care as a public utility through which states create a common fund that pays practices directly. Insurers could still compete on other lines of business. I’ve heard worse.
  • The ACCESS Model for Medicare goes into effect on July 5. With 150+ participants already lined up, Second Opinion posed a reasonable question: What about ACCESS for Medicaid? Makes sense to me, especially since states have embraced managed care.
  • When it comes to rural health transformation, the numbers don’t add up. As $50 billion in federal aid doesn’t equal nearly $1 trillion in losses, states are focusing on cost-cutting strategies, not innovation. Good job, everyone.

Happy summer, Northern Hemisphere. If you know me, you know this is my least favorite time of the year. (And if you don’t, well, now you do.) If you need me, I’ll be under an oscillating fan, within a foot of an AC, and waiting until the humidity breaks to do anything that will cause me to begin to sweat.

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

~ iambeastwood ~ 1 Comment

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.

The Beastwood Files: May 2026

~ iambeastwood ~ Leave a comment

I survived my marathon, helped my son adhere hundreds of monster truck stickers to sheets of paper, took my mother to two doctor’s appointments, installed our window ACs, and wrote a few things here and there to boot. In other words, just another month here at Brian Eastwood Writes, LLC. (And I was named Employee of the Month AGAIN!)

Stuff I Wrote

Things I Did, Marathon Edition

  • Finish my 5th consecutive Vermont City Marathon (and 6th marathon since my won was born) within the two-minute time window of 3:24:31 to 3:26:31 (in this case, 3:26:23), which means I’m officially nothing if not consistent
  • Gather acceptable snacks to share with my son at the finish line, including slices of pizza, Nutri-Grain bars, and the all-important free underripe bananas that are the reason like 73% of marathon runners compete
  • Wear brand-new compression socks to recover from said marathon because I forgot to pack them and had to purchase a new pair the day before the race
  • Remember to pack everything else that mattered – including the cowbell than my son shook vigorously while in the hotel room but not (AFAIK) while outside cheering for runners

Adventures in Fatherhood

  • We completed / survived our first-ever Kid Race, which was a 1/2-mile loop in Burlington, Vermont’s lovely Waterfront Park. We also overcame our pre-race jitters, which were 100% attributable to the presence of mascots in unexpected proximity. We celebrated with pre-packaged trail mix and a sampling from a local ice cream truck.
  • We also experienced and enjoyed our first-ever roller coaster at a local fundraiser fair, though our favorite part very well may have been the fried dough. (Can’t argue with that.) We decided we didn’t like the teacups – and I learned I can’t handle the teacups as well as I used to – but did like the Ferris wheel (even if the waiting was the hardest part).
  • Yes, we heard the sonic boom from the meteorite that landed in the middle of Cape Cod Bay. No, we didn’t think anything of it at the time, especially as our neighbors are in the midst of a large renovation project and it hasn’t been uncommon to hear things get loudly dropped into a Dumpster.

Enjoy June and the beginning of summer. We’re gearing up for a pre-summer-vacation trip to Cape Cod , preschool graduation, and a trip to New Hampshire for the Fourth. We’re NOT going to New Hampshire in June because I told a story once about black files and now we’re convinced that’s when there are YUCKY BUGS in our neighbor to the north. I’m sure we’d have fun, as we talk about the YUCKY BUGS while laughing, but between Champy and the teacups, I’ve scarred my son enough for quite some time.

This Month in Digital Health News: Making AI Meaningful, Managing Climate Change Risk, and a Bunch of Other Stuff

~ iambeastwood ~ Leave a comment

It’s time for This Month in Digital Health, where I highlight news articles that caught my attention and offer my take on why I think they matter. Along with the requisite stories about AI in healthcare, this month – fittingly when the Boston area is about to hit record high temperatures for this time of year – we’re looking into climate change and healthcare.

It’s all about meaningful AI utilization now. As half of healthcare organizations have now deployed generative AI, according to a McKinsey survey, attention has turned to tool integration and ROI. That means leaders are looking for meaningful transformation, not even more revenue cycle automation; that often comes down to using AI to solve readily identifiable problems. Meanwhile, because we just can’t have nice things, HHS wants to ditch requirements for transparency in AI tools, because reasons.

Add “climate change” to healthcare’s risk management agenda. First, the bad news: Hospitals in areas vulnerable to climate change haven’t done much to address climate-related health risks, in large part because of socioeconomic disparities. Next, the good news: Looking at climate change as a health equity issue and using existing long-term planning frameworks can help manage these risks. Plus, hospitals are reducing waste – no minimal matter, as the industry accounts for more than 8% of carbon emissions – and EMS and mobile clinics are buying hybrids.

Now, for a bunch of interesting odds and ends.

That’s all for now. Tune in next month when I’m sitting in front of the AC waiting for summer to end even though it hasn’t technically started yet. (One of my most unpopular opinions is that I strongly prefer the colder months of the year.)