The 3 Big Ideas

An intro to the work-world changes behind my business

After a year hiatus, and never quite finding my algorithmically-driven-content-groove on LinkedIn, I’m coming back to Substack. Longtime subscribers might notice that I’ve renamed the publication from “Ops Drops” to “On Work” — the change reflects my excitement to write more broadly on fractional work, portfolio careers, and the people I admire who are building their professional lives in ways that work for them.

For today’s first issue back, I’m kicking off a 4 part series to explore the 3 Big Ideas on work that I’ve been obsessed with these last few years (nothing like a big public commitment to start the new habit!). The following three weeks will explore each of the 3 Ideas in their own issue, and, like today, I’ll also include some a link round up at the end if you want to read more on these topics.

Let’s get into today’s content.

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I’m entering the third year of building Hello Generalist, which is a pretty wild thing to name. Some of you know that I started the company in a 48 hour adrenaline-slash-boredom-induced-sprint while my partner was out of town — it was one of those flow moments where the idea hit, I wanted it to exist, and then I didn’t get up from my couch for 2 days until a website was up.

The cool thing about working on something for several years is that the swirl of big ideas in your head starts to congeal. Despite it’s almost accidental start, HG was born out of a few of those swirly, loose ideas that I’ve come to understand more now with time.

I named the whole company after a personal experience: I had quit my full-time job six months prior, and was loving doing part-time, contract work with startups. I found it interesting that I was having success in the contract work world, even though my resume (filled with startup madness) looked nothing like the typical contractor (people who spent their whole career doing one thing). I had plenty of expertise, but not just in one thing.

At the same time, I was also building other income streams — I started a coaching practice. I built an online course. My partner and I started to make cash-flowing investments. And as I talked to friends around San Francisco, they shared these desires, wanting to use their hard won skills broadly, and finding more freedom in the process. A growing subset of smarties, who all had windy backgrounds like mine, wanted to tap into their own independent careers.

I’ve come to realize that behind these swirly experiences lie 3 big ideas — unique, though related and overlapping — that shape Hello Generalist, and are shaping this chapter for the work world more broadly:

The First Big Idea — Fractional work is on the rise

Fueled by tech layoff panic, and post-Covid life rebalancing, a new group of people suddenly want contract work. In particular, formerly full-time tech leaders want part-time work across several companies, bringing their skills from one to many, while still maintaining income stability. For startups, this is huge — the people who used to cost them $250,000 a year (plus taxes and benefits), are now a fraction of the cost for similar impact.

But what’s more, I think there’s a big identity jump going on here too. The world of “contract work,” long reserved for “consultants,” is now open to people who would never call themselves a consultant (as I raise my hand). The door’s now open to a new class of people who were exceptional full-time leaders, and who get to share their skills more broadly now because of it. Plus, startups have always been allergic to hiring consultants — Experts? Yes, always. But a finance person who’s only ever done one thing in one industry? A marketer who only offers one skillset? Someone who just gives advice? No. Startups need affordable, expert doers, and fractional work is the answer to that.

The Second Big Idea — The High Value Generalist

Put simply, High Value Generalists are people who have developed top 5% skills in more than one area, and they get to do pretty much whatever they want professionally because of it.

There’s many ways to get to this point in your career, but one path that I’m especially interested in: People who dabble across industries and roles in their early career > followed by break-out, credibility building depth in an area or role > and that unlocking the trustworthiness to share their skills broadly.

In my mind, successful (and sometimes, well meaning, but very unsuccessful) startups are breeding grounds for this person. Early stage startups survive on people who own lots of things at once, and as the startup grows, the best of those same people become leaders for specialized departments. An experience like that is nothing but a perspective builder, let alone a credibility marker on a resume. I’ve loved watching these people now pick their professional path, be it fractional work, coaching others, writing online, teaching courses, investing, advising — the list of choices goes on, and thanks to the internet, new pathways for High Value Generalists open up all the time.

The Third Big Idea — Portfolio work diversity

Not really gig workers, not only creators, perhaps not just fractionals either. Those building a Portfolio Career (another identify shift among the 3 Ideas) include the movement of tech workers breaking out of the 9 to 5 single-income structure, opting to build several income streams instead. The overlap between the first two Ideas should be pretty clear here: Many High Value Generalists pursue fractional work as part of their portfolio, which might also include coaching, online courses, investing, advising, and so on.

I know you see this play out online (easily spotted on LinkedIn), as smart people promote projects outside of their traditional work. I get so excited seeing people stack up income streams, buying laundrymats, launching paid Substacks, landing podcast sponsorships, let alone booking fractional work. The smartest people I know are de-risking their core income with a portfolio of income streams that often serve them emotionally, not just financially.

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Over the next 3 weeks, I’ll share an in depth view on each Big Idea in three separate posts, bringing in real examples from my life, the lives of HG members, and the experiences inside our customers’ businesses. I hope you’ll read along, and I hope you’ll share your feedback with me as it’ll help me fine tune these ideas even more.

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If you want to go deeper into these ideas, here’s a glimpse into what I’ve been reading, watching, and listing to this week.

• I’ve been thinking a lot about what “playing my own game” means to me, and really appreciated fellow Portfolio Careerist and Substacker Anna’s piece on old rules we might consider abandoning in favor of more freedom. The money framework she references reminded me of this other post of hers, which I often recommend to aspiring independent workers.

• As an exec coach and person on Earth, I loved this point of view on dealing with anger at work from Natalie Rothfels on Lenny’s Newsletter. It’s a deeply practical guide for walking yourself through big emotions that inevitably come up at work. And also worth saying that, uhhh, this stuff is HARD to do alone — Coaches can be great helpers.

• Have you seen the Fractional Rates Survey? You can access the survey’s Looker Dash when you contribute your own data. I’ve been revisiting the data this past week, and it’s gotten pretty great over time, now with close to 900 participants from around the world.

• Two worthy TikToks (sorry, not sorry) on Generalists that are spot on: On tech jobs in a post-AI world, and on skill stacking as the most underrated career upleveler

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Be well! Until next week, Shaina