👋 Hey, it’s Shaina, and I’m back for another issue of On Work, the weekly letter on independent entrepreneurship, fractional work, portfolio careers, and more.
If you’re new, hi! Welcome. Help me spread the word by sharing with your friends, and please say hello in the comments.
I’m introducing a few new columns to this Substack. And today is the first issue of Open Tabs — ta da!
As someone who is very online, I encounter a downright feast of good stuff on independent work that I want to share with you. Plus, I get a birds eye view into what’s happening in the industry first hand, as I chat with operators from HG and MO.
This is my place to share what I’m reading and learning with you: the people want the links, and the people want the tea. I am here to deliver.
Elena makes the case that we’re shouting from the rooftops: as AI comes for our knowledge work jobs, the single most rational thing you can do right now is build something of your own. A side project, some type of content, a Mom-and-Pop SaaS, a personal brand, whatever.
Ever think about how much info LinkedIn holds on your network, but does nothing to show it to you? Logan shares how she’s using Claude to tap into it visually. A great primer to get you started on your own search.
Go Fractional released their “State of Fractional Work” report. Some genuinely worthwhile insights around pricing and popular roles. (Heads up, it’s an email-gated download).
I don’t know if this is inspiring or terrifying to me, but here’s a clip of how one founder is straight up copying successful apps and businesses — and making $20k MRR from it.
Carta’s constantly publishing incredible reports, and this one on solo founders caught my eye for self-evident reasons. They’re mostly looking at solo startup founders as opposed to the classic 2 co-founder combo, but I think this trend is a happy indicator of what’s possible for entrepreneurial people of all kinds.
Rachel shares the 3 things she’d do if she was trying to start an AI-ops consultancy again today. (Raise your hand if you’re trying to do this?)
As HG and MO enter their next phase of building (and as I begin working with a new teammate for the first time in a while), I’m revisiting the old classic texts on what it means to build a calm business. This is a great explainer if you’re new.
An oldie I was revisiting this past week: The breakdown of Justin Welsh’s portfolio. If I’m right, I think his solo portfolio has since crossed the $2M mark.
I’ve been a fan of Rachel Karten since her Bon Appetit days, and it’s so cool to see her Substack reach 5 years. She follows the model many of you follow: use content to fuel her independent business, which, in her case, is social media work.
I am trying to bring more elements of matriarchy into my business (cyclical and regenerative, democratic, flexible without rigidity), and Laetitia Vitaud gives me a very hopeful view for a future where women over 50 get superpowers at work with AI.
In closing, may this little ditty be your mantra for the week.
One of the things I love most about our movement: there’s no single right way to do it. You can hold a full-time job and start a side thing. You can move in and out of working for yourself and working for others. You can dive in whole ham and work for yourself entirely.
This past week I talked with two of you in the middle of that maze.
One has been independent for a couple of years, doing fractional AI product work with startups. Recently, she hit it off with one client and went full-time with them. She was wary at first, but they landed on a beautiful arrangement: she delivers for them, and they let her keep working independently in the margins.
The other person is at the very start. She’s full of ideas for products to build and people to help, but hasn’t booked work yet. While networking, she tripped into a full-time offer that pays the big bucks and puts her in front of the exact clients she’d want later. Her bank account and her network, both handled in one move.
Taking a full-time job can feel like giving up on the dream. Did I quit too soon? Did I give it a fair shot? Is the chapter over if I go in-house with these people?
I’ve done this myself. A few years into building Hello Generalist, we moved to London, and in classic form, I went looking to fill the boredom and discomfort of a new city with work. I took a full-time job on UK hours, ran HG at night on US hours, and kept it up for about ten months before I left. A few well-known portfolio career writers have made similar moves.
This, my friends, is a glorious two-way door. You can walk through it and walk right back out. There’s no good-boy, bad-boy morality to taking the paycheck. Take the job, go all in for six months, then start folding your own thing back in. Take the job, love it, and keep it going.
Several HG roles lately don’t want a fractional to help with ops. They want someone who can do the AI work and lead the company through the change. Come run our AI transformation, build the automations, coach the team while you do it. I see more and more of this every month.
On the other side, a VC told me her founders are starting to say they’ll just use Claude instead of making the ops hire they used to make on day one. That AI can last them through the early days when they might hire fractionally. I’m skeptical of this one, as AI still needs a person to run it, and Founders are busy, but we’ll see what changes over time.
My pov here is that the job is still there. But what’s changed is what they expect you to know and do. The fractionals I see regularly winning right now bring real judgment to the tools instead of pretending the tools aren’t there.
In what was one of the most hopeful and feel good chats of the week, one Fractional HR leader told me both of her current clients came from being genuinely useful in a Slack community she’s part of. Her whole business development plan is a post-it on her desk that reads “be helpful.” She jumps in to help people who need it in the community, and the work follows.
Nice, right?
Any other must read, watch, or listen links you’ve got open right now? Thoughts on the chats I’ve been having this week? Would hear it in the comments.
Before we wrap, a few shameless plugs. If you’re into the ideas I write about, here’s a few ways for us to work together:
Want 1:1 time with me to talk about building your independent business? I’ll show up judgement free and candid, and make this hour a super valuable one for you. You can read more and book that here.
If you’re a startup who’s curious about fractional hiring, or a startup operations pro pursing fractional work, check out Hello Generalist.
If you’re a fractional, consultant, coach, or other flavor of independent operator wanting to build real sustainability in your business, check out Manual Override. Our Fall 2026 cohort applications haven’t opened yet, but please sign up for updates to hear once we do.
Until next time, Shaina
Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.