👋 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.
Is this a pilot? An experiment? A mini-series? We’re not sure yet. But here we go!
Up today is the first episode of Operator Hotline, a call-in show for people building independent portfolio careers, hosted by me and Harry.
Watch the full episode on YouTube
Think of it as Car Talk for people who work for themselves (shout-out to Click and Clack the Tappet Brothers, a la 90s NPR).
Harry and I spend our days talking with people from the Manual Override and Hello Generalist communities — people who are building independent portfolio careers. They share challenges with us that are deeply universal, and usually, they’re things we’ve been through ourselves. We wanted a way to share those conversations in hopes it helps your week even just a little bit.
For this first episode, we took questions from three wonderful people: Elaine, Jenna, and Zeina (each a delightful follow on LinkedIn).
Jump to their questions in the episode, or read through the transcript below:
(01:40) Elaine, part 1: I undercharged my first client. Now what?
(11:36) Elaine, part 2: I’d so much rather do the work than post online. Won’t work just find me?!
(27:00) Jenna: How do you do client work and BD work at the same time?
(38:00) Zeina, Part 1: How can I pick between a stable W-2 and the thing I’m building on the side?
(50:00) Zeina, Part 2: Is posting online just procrastination in a nice outfit?
“My first client gave me my start. I was early in launching my practice and needed a win, so I took the engagement at a rate I knew was below where I wanted to be. It’s now six months later, two contract extensions in, and the rate remains slightly lower than my target. The relationship is good, the work has been good. How do I renegotiate my rates without damaging the relationship?” — Elaine
Shaina: The most important context around Elaine’s situation is that this is her first client. The client who gave her her start, who gave her the momentum to work for herself and kick off this chapter of her career. And in what is a tale as old as time for fractional and consulting work, you undercharge your first client. Drastically.
Harry: Drastically. Yeah.
Shaina: So, Harry, what was your first client paying you compared to what you charge now? What’s the difference?
Harry: That first client was at a rate where I knew I wouldn’t be making what I made full-time. Now, I’m making more than I was full-time. So it bottoms out at the beginning. You get the experience, build the network, and grow from there. I think this might genuinely be the number one question on the mind of everyone getting into this.
Shaina: Right. “My prices are too low. I’ve realized I’ve undercharged. I haven’t accounted for my expenses, my time, my expertise, the value I bring to an organization. Now that I’ve realized it, what do I do?”
So, Elaine, you’re in the universal first-year-of-working-for-yourself experience.
Harry: And what’s interesting is that she started with a two-month contract, then six months, then two extensions. That’s a very good sign. In a short amount of time, she’s getting confirmation that she’s bringing real value to the company. For a first client, that matters. There’s plenty of other experience out there where the first client just isn’t a good fit and it’s demoralizing. Elaine is on the right path.
Shaina: That’s a great gut check for anyone in this situation. Elaine is in a really positive moment: the client’s a great fit, she’s doing great work, they see it, she feels it, and they want her to keep going.
She’s also in a smart position because there are renewal points built into this work, whether she negotiated them into her initial contract or they came up naturally. That’s a great thing to write into a contract, especially in your first year: some kind of three- or six-month check-in point, rather than an open-ended arrangement with no renewal moment.
Harry: On that point, though, a lot of people bring up the idea of building automatic increases into those renewals. I’m actually against the automatic increase. Not because it’s a money grab, but because you probably leave money on the table for a better increase if you genuinely believe in the work you’re doing. I think that’s where Elaine is now.
Shaina: So how does she actually do it?
If I’m Elaine, the first thing is getting clear in my own mindset. A renewal isn’t just reaffirming the same contract. It’s a renewal for a reason. You’ve proven your value, and you’re likely moving into the next chapter of work with different deliverables and different goals. You’re updating your standard rate in due course. There’s no cleaner situation than a natural renewal conversation to lean into a rate increase.
I wouldn’t spring a new price on them out of the blue, in between renewal moments. But at the renewal, I’d approach it with gratitude and joy for the work. You’re excited to continue, and your standard rate is changing. Share the new rate and leave it at that. Have that conversation in person or over the phone with a contact, take their temperature, then follow up in writing. That should just be standard practice. What’s your take?
Harry: In the operator space this can be hard to do. If the underlying business hasn’t changed over a period of time, it’s harder to make the case for that business to stick with you specifically at a higher rate. It’s a much easier conversation if you can look back over six months and point to something. Elaine’s in the HR space, so is there a new or changed responsibility? Does the founder now see more value in someone like her because the business changed? It doesn’t have to be a change you made. The environment around you may have shifted so that you’re now more (or in some cases less) valuable.
There’s also opportunity cost on both sides. They have the option to work with someone else, so what’s the cost of that? Is it worth them not making the jump and paying you more, versus finding someone else who can do the same work, maybe at a lower rate? And for you, there’s the opportunity cost of taking one client over another. In my space, AI consulting, where there’s a lot of movement, some people I’m close with will price a client by asking, “What if I took that other opportunity at this rate?” Not as a bargaining chip, but internally, to come to terms with what your rate actually is in the market, not just what you think it’s worth.
So it’s nice to say “the price has gone up,” but there needs to be some rationality to it beyond “I think I’m worth more.” You have to make the case: through your direct impact, the changed environment, or the market opportunity elsewhere. Ground the conversation in one of those three buckets and it becomes a business decision rather than an emotional one.
Shaina: And for all of us in this situation, every pricing conversation gets easier when you have a pipeline of future opportunities. That’s the hardest part here. You can hear the fear in Elaine’s voice: “What if I ask for more and they say no, and then I’m out of a client? I don’t want that.” That peace of mind from having other opportunities is really important.
So, Elaine, our advice is two things. One: think clearly about what’s changed inside the business and about the deliverables, and get ready to make your case. Two: make peace through your pipeline. That’s where the comfort comes from, knowing that over time you can find the next client, so that if this one won’t convert or won’t raise its rate, you’re ready to move forward and still take care of yourself and the health of your business.
“I’ve been building my HR fractional practice for a couple of years now, but every time I sit down to write a LinkedIn post or a cold outreach message, it just feels like I’m performing. It doesn’t come naturally, and I know I’d rather do the work than talk about the work. I have 20 years of experience, companies I fixed, messes I cleaned up, results I can actually point to, but my instinct is to keep my head down and trust that work will find me. My question is, how do you build pipeline when self-promotion just doesn’t come naturally?” — Elaine
Shaina: Elaine’s follow-up is ultimately about pipeline building, which is the right framing for this year. She’s trying to find new customers, new referrers, new ways to meet businesses she can help. She’s bought the hiking shoes, signed up for AllTrails Pro, started up what we’re calling Cringe Mountain (posting online), and gone, “I don’t love this. What do I do?”
The framing that helps me: there are really only two ways to build your pipeline. One, you do things on the internet that make customers find you and come to you, like posting online. Or two, you identify businesses and people in or near your network and go to them, the sales-team motion you’d recognize from a past startup or tech job.
Something comforting to ground this in: to work for yourself, there is no requirement to be internet-famous in any way. You do not need to reach for internet fame. It really helps to reframe it. Not “I’m building a giant audience to become an influencer,” but “I’m sharing my point of view and having scaled conversations through these platforms.” And that does not replace the one-on-one effort of identifying businesses and contacts and going to them.
Especially in the first couple of years, almost everyone I know has booked customers through people they already know. So in the “go to them” versus “they come to you” duopoly, if you’re getting stuck on posting online, that’s okay, as long as you’re still reaching out to people and having those individual conversations. That’s the framing to put on top of this whole thing.
Harry: I have strong opinions here, on the point of posting online. I’ve been doing it for about two years. At first I thought it was one thing, and that made me hate it. Then I realized what it actually is, and that changed everything.
I’ll end up on calls where someone says, “I’ve been looking at your content for six months.” And I think, fantastic, how about you drop a little engagement so more people see it? But they don’t, because there are people on the other side who don’t read the algorithm. They read it as a human.
The point I’m getting at: people are reading content, at least the content that’s helped me in my work, as a gauge for what a lot of people in AI are talking about right now, which is taste and judgment. Have you heard of Notion’s hiring equation for full-time hires?
Shaina: No.
Harry: I might butcher the math, but the three variables are capability, agency, and taste. Capability: do you have the experience to do the job? Elaine’s got 20 years, so capability, great. Agency: will you go above and beyond to hit the goal? Also great. Those are the two things people over-focus on in their content, showcasing experience and agency. But a lot more people today care about the third component: taste. Honestly, do I just vibe with you? Do you take yourself too seriously? Would you fit the way I think? How do you communicate?
In my space, I’m not the most technical, I’m on my own, and I don’t have as much experience as others. But people hire me because we generally get along and I get the job done. So what helps people get up Cringe Mountain and onto the trailhead is knowing that people read content to get to know how you think and communicate, more than what you’re literally saying. Do that, and you differentiate yourself and end up with the engagement you actually care about: someone quietly following you for six months because your thinking resonates. It’s not about likes and comments.
One tactical thing: LinkedIn is terrible at surfacing it, but if you go to the analytics of any post, you can see how many people saved it, and saves are typically much higher on the genuinely valuable posts. So from a content perspective, it’s more of a vibe check: could I get along with this person, could I have a conversation with them, more than what you’re technically writing about. That makes it far more interesting to engage with than trying to invent some new framework and getting in your head about it.
Shaina: You’re riffing on something that’s very true right now. Didn’t you tell me something like 40% of posts on LinkedIn are AI-generated?
Harry: Yeah, around 40% of long-form posts and 30% of short-form posts are flagged as fully AI-generated. Someone goes to Claude or ChatGPT, writes a post, and dumps it into LinkedIn.
Shaina: And hearing that, it tracks. So for Elaine, the bar is not to outperform some machine content strategy that’s just pumping out AI-generated stuff. You skim right past that, and everybody knows they skim past it. What you don’t skim past is a real person: someone whose post makes you want to keep reading, have a laugh, learn something, and save it for later. The bar isn’t to outperform the machines. The bar is to show up as a person.
Here’s another metaphor I’ve been playing with. I get caught up in the idea of becoming some giant audience-builder, and I hate that. So I went back to 14-year-old Shaina, who just wanted a really cool corner store in her neighborhood. Sling some tacos and coffee, pour some great wine at night. The vibe of a wonderful local business, with regulars and people you have an ongoing dialogue with. That’s the mindset I’m trying to adopt. I’m not building an audience, I’m building regulars. I’m building a small business, my small pocket of the internet, where I can share what I know as a human and engage with the regulars who want to come and the newcomers who stumble in.
Harry: There’s also a push now that says: if I’m not going to push AI slop, how else do I stand out? A lot of people have built followings by being energetically, actively weird. “Be more weird on LinkedIn.” And it can feel like you have to perform the most human, anti-AI version of yourself. But my posts are honestly kind of boring. The topics aren’t the most exciting, I’m not sharing personal stuff, they’re just written the way I actually think. And that’s what’s landed me pipeline more than anything else: sharing a unique way of thinking, your actual breakdown of a situation, how you’d communicate it.
People will even reach back out using the same way you explained something. You start to see them explain it to their team that way, and you realize, that’s why they brought me in. Something clicked in how I think and communicate, which is what people actually care about. Sometimes just ask: if I were on the other side, would I want to hire this person out of everyone out there? If your post is pure experience with no personality, it’s hard to differentiate from everyone else with 20 years in HR. The only thing you can really differentiate on is how you personally think and communicate. So focus on that. Don’t try to be the expert everywhere. That’s very hard in a space full of experts.
Shaina: Last thing, tying it back to “go to them” versus “they come to you”: remember, posting on LinkedIn is completely optional. You don’t have to do it. An even more effective move, especially early on, is to put together your 30 to 50 closest professional contacts, the helpers who care about your work, and send them a quarterly email. Here’s what I’m doing, here’s what I’m looking for help on, here are some stories and pictures from recent work and life, and I’d love to hear what’s going on with you. Especially when you’re starting out, that builds your pipeline quickly. It gives you the conversations that create momentum. And then, over time, find your voice for posting.
Remember: nobody remembers individual posts. Nobody’s tracking how many likes yours got. Nobody’s judging you for what you put up. What sticks is that your name shows back up in the feed enough times that when the need arises, say, for an experienced HR leader, they think, “That’s right, Elaine. I should reach out.”
Harry: That’s the craziest thing. The long game exists, but it’s way longer than people think. The most random opportunities I’ve had came eight months later, because someone saw a bookmarked post from eight months ago and now they have that problem. And there’s a real glorification of how much pipeline LinkedIn content generates. I wonder how much of that is people saying it to drum up their own business. Don’t read everything on the internet as truth.
Shaina: So what’s our point? If you’re starting out and need to book work to pay your bills: talk to the people in your network, tell them what you want to do, find businesses you’re a great fit for, find warm introductions, and go to them. There are endless ways to go to them that feel authentic and like you. The LinkedIn game, the Substack game, the posting game: an incredible way to develop your point of view, show up regularly in people’s feeds, and build pipeline over the longer term. But for fractional work you only need a couple of clients at a time, and you could very easily get through your first couple of years through your immediate network.
So, no stress. If you don’t want to climb Cringe Mountain right now, it’s all good. It’ll be waiting for you a couple of months from now, after you’ve exercised that network.
“Hi Shaina, hi Harry, I’m Jenna. I left MBB consulting last year, and since then I’ve gone solo as a fractional head of product. I’m currently learning how to juggle pipeline development, smooth ramp-offs, and ramp-ups. I’m thinking about how to keep momentum on the business development side running, as well as social media outreach, replies, and so on, while in the thick of client delivery. AI is great, but the personal touch wins out when you’re building relationships, so the time sink is real. I’d love it if you could share your thoughts on this.” — Jenna
Shaina: This is the problem of working for yourself, and it’s obvious to say out loud but genuinely scary to feel: when you work solo, you have to do a lot of things all at once.
Harry: And it’s fun to do them, until you get a client. Then it’s, “Oh no, this actually worked. Now I have to keep doing it and the client work.”
Shaina: Exactly. What Jenna’s trying to avoid is smart: she’s booked some work, but she’s already thinking ahead to when it runs out or ends early. This is the chasm we talk about in Manual Override, the thing that separates someone working as a contractor for a chapter from someone building a sustainable business, someone showing up like an entrepreneur building a business around their skills. Jenna’s thinking about that core system for how to do both sustainably. Hats off to her.
Harry: There’s a trap we also talk about in Manual Override: everyone gets obsessed with the website, the LLC setup, all of that. And the natural instinct is to treat business development like what you already know. In our tech world, that’s the B2B SaaS sales process, a whole system with all its quirks. That over-engineers what you need to do regularly.
One thing I learned from someone I respect highly, who’s built his business purely on word of mouth with very little outbound: it comes down to “I deliver great work for my clients, and I set up a way for them to tell others about me.” That’s an underrated form of BD. So to start, I think people overwhelm themselves with everything they could be doing on BD when it can be simpler.
Shaina: It’s very hard to be online and tell yourself a story about the incredible brand and content system other people seem to be building. In reality, especially in your first couple of years, and especially when you only need a handful of customers at a time, you’re not building a consumer product charging ten bucks a user. You’re charging many thousands of dollars per customer per month, and you don’t need many of them to hit your financial goals. Simple things work.
Like a quarterly email. When I first started Hello Generalist, my first 10 or 15 customers came from an email I wrote to my professional friends: former managers, the founder of the startup I’d worked at, my smart and well-connected work friends. At first I sent it every other week, with stories, pictures, anecdotes, asks, and updates. Over time it became quarterly. If you’ve worked at a venture-backed startup, it looks a lot like an investor update. It’s a low-effort, high-impact thing, far more so than telling yourself you need brand messaging pillars and a content calendar across three platforms.
Harry: I’d also break it down to the simplest thing you can do in 30 minutes a day. And, Jenna might hate me for using this word, because it strikes fear in every former consultant, what’s your ideal utilization for client delivery, and how much time are you actually dedicating to BD? If client delivery is 80 to 90% of your time, then right now you may be on a contract rather than building a business, and you may just not have the space for BD. That’s not necessarily Jenna’s case, but I know people who tried to do it all and found it hard.
If you can dedicate even 15 minutes a day to one BD action, it accumulates. Over a week or two you look up and realize you sent 60 emails to people in your network, or reached out to a bunch of people on LinkedIn just to learn about the problems they’re having. That adds up more, exponentially more, than you’d think. A small single habit is great.
The other thing: your client delivery is itself a unique data point for BD. Going back to the taste, capability, and agency equation, when you can showcase the work you’re actually doing and build trust, whether through content or in how you connect with someone, and tie it back to real client-delivered results, that has real staying power. So use your client delivery to feed your BD. You’re not starting from scratch. Find some avenue to take what you’re doing each week and fold it into something that helps on the BD front, even just reconnecting with old colleagues.
Shaina: Really well said. I want to revisit your utilization point, because it’s an interesting checkpoint from a business-planning and pricing perspective. An exercise we encourage: what’s your goal income, and how many hours a week do you want to work? Within those hours, you’re saving time for administrative work and for business development. The time left over for utilization is priced accordingly, so you’re not cutting yourself short by failing to pay yourself for admin and BD.
So this might be a good moment for Jenna to check in on pricing and ask: “I want to preserve time to show up online and do BD. Did I overbook and underprice myself? Is there something I can adjust as I take on the next customer?”
“I left my last full-time role earlier this year, and I’m building independently: fractional work as a customer revenue leader, a newsletter for people figuring out what comes next in their career, and a few productized program ideas up my sleeve.
I’m about three months in. I gave myself a deadline to choose: go full-time fractional, or go back to a full-time role, maybe one more in line with what I’ve learned from all the tinkering and building this summer. Ideally I’d like that answer by the end of the summer. The problem is I’m running both tracks at once. I’m in two active full-time processes while also trying to build up my fractional pipeline, and the energy is completely different. The full-time track is responsive and quick, with a well-known process behind it. The fractional track is very self-directed, which means I find I drop it when other things come rolling up. My ultimate question is: how do we keep momentum on the thing we’re building while there are other things happening in the background?” — Zeina
Harry: Zeina’s on a dual track, balancing the potential of a W-2 with the potential of what she’s building on the side. She’s experimenting with a lot of really cool ideas but wants to make sure she’s got a business going, or at least income coming through the door. A lot of people in their first year feel this pressure: is this actually working? Do I have the timeline for it? The first thing is, she’s done a great job of setting a timeline for herself.
Shaina: I relate to that. When I was starting out, my timeline was really a budget: a number from my savings account that my partner and I agreed I’d spend to explore this and figure it out. I knew my monthly spend and bills, so the budget came with a loose timeline. As a household, my partner and I knew me working for myself would have real benefits in our life, which, many years later, has proven out. So we took an almost mathematical approach: what’s this exploration worth to us as a family? How much are we willing to risk and budget? And at the end, we’d be okay having spent it on the exploration even if nothing came of it and I ended up in another full-time job. Glad, in hindsight, to have spent it if it led to this next chapter.
So if you’re in a similar spot, sometimes the move is a conversation. At the dinner table with your spouse, partner, or roommates, or with yourself: “This is the amount I’m willing to spend on this. This is roughly the timeline. I give myself permission not to spend all of it, and not to earn a single dollar.” Very practically, that’s a helpful planning process going into this chapter.
And Zeina is exemplary of so many people starting out, in that the result feels binary: either I’m working for myself, or I’m back at a full-time job. The first thing I want to grant is permission and grace. One of the most powerful things about a portfolio career is that it isn’t binary. Many people hold a full-time job and work for themselves. Many work for themselves for a while, layer in a full-time job, then come back to it later. There’s no one right way. We’ve seen endless people in the Manual Override community and the Hello Generalist network do both, and move between them. They can coexist at the same time.
Harry: There is a gut-check moment, though. If you’re applying for full-time jobs, you left your last one for a reason, whether something was off or you saw an opportunity ahead. So I’ve dabbled with the question: what would my criteria be to take a W-2? Lay that out. Then imagine you had the two ideal contracts, one from each side: the ideal W-2, or the couple of fractional or service engagements you’re exploring. Which would you sign first? Then ask whether that actually fits the timeline and the logistics, not just the gut feeling.
So it comes down to: would you actually put pen to paper on that W-2? If that’s not a 100% “yes” gut feel, that’s where I’d start to think harder about where I put my energy. It doesn’t mean every W-2 is wrong. It just means there’s a limited pool of companies and roles you’d really want. The more you can make the decision real up front, even hypothetically, what would it actually mean to take this W-2, the better. Does it mean sacrificing everything, or could you still, say, keep doing the newsletter she mentioned to help other people? Maybe that ebbs and flows back into something later. Making the decision point as real as possible opens up where you want to put your energy right now.
Shaina: You’re talking about something we discuss a lot from a mindset perspective. The big question to look in the mirror and ask: am I running away from something, or toward something? At Hello Generalist we get applications and talk to so many people running away: from a bad boss or company, from layoff trauma, from the fear of not being able to pay their bills. All of those can lead to a panic move: “I’m just going to go work for myself, pick up some contract, and do it.”
Sometimes you’ve got to do what you’ve got to do, take the work in front of you to pay your bills and take care of your family. There’s no shame in that. But when you actually have a choice in front of you, it helps to ask: am I running away from the dumb full-time job I hated or could get? Or is my mindset one of chasing this opportunity, running toward this next chapter and all the benefits of working for myself? For Zeina, deciding how to use her time might come down to that check-in: what do I really want, and what can I do today to get a little closer to it?
Harry: It’s also about expectations. Staying true to what you want to build. My own business has shifted from a fractional-ish world to more service-based work, and people ask, “Couldn’t you scale that by hiring more people?” The last thing I want to do is hire anyone. There’s a reason I work for myself. But there’s always this nagging pressure that you could be doing more, that it could be bigger. People feel it with the W-2 too: in the first and second year, you often haven’t hit the income you used to make, and you think, “It’d be much easier if I just took this W-2.” Well, how much effort are you putting in for that income, and are you doing work you like for it? Sometimes I get distracted by other people’s expectations of me, which they don’t actually have. I create them in my head. So I’ve got some work to do there myself. But that’s where these decisions get influenced by factors we can’t control or shouldn’t be over-weighting.
Shaina: What’s the big lesson? The path is made up. There’s no such thing as the path. You get to decide it. The sooner and more consciously we pick the path we want, budget ourselves to go down it, give ourselves the freedom and flexibility, and get buy-in from the people in our lives, and know that these things can coexist, the better.
Because there is no path: find a great full-time job that checks all your boxes? Amazing, go kill it for the first three to six months, then start layering in your other projects. Start working for yourself, take on a couple of contracts, and hate it? Cool, go back through the door you came in and get a full-time job. There’s no such thing as a path; it’s made up. This is all a two-way door. You can always walk back through. And this is all a simulation.
Harry: It’s all a simulation, yeah.
Shaina: Good luck to Zeina as she figures it out.
“I’m also building my personal brand. I’ve started a newsletter, and I’m posting on LinkedIn three or four times a week. The open rates are good and engagement’s good, but it’s a slow burn. Audience building doesn’t happen overnight, and the fractional pipeline is hopefully going to come together in the next three months, but it’s a very different energy and different tactics.
So how do we balance those two? What’s my priority right now? And the big one: how do I know when content creation has quietly become my productivity avoidance tool? I’d really love some help with that. Thank you guys so much.” — Zeina
Shaina: Posting on the internet is a head game. We freak out about it all the time. We’ve already heard from several callers freaking out: how do I make this work? Is everybody judging me and thinking I’m dumb, looking at everything I post? It’s hard.
Especially for smart people who can picture what a really good system, or a great scaled brand, would look like. My fellow strategists (said with derision): we really want a system to plug into. And if you’re like me, boy, do you want to waste some time defining your brand pillars, or getting Claude to build a content calendar, and then a system that automatically sends you the thing so you can write it and hit post.
A data point to ground this in: as of 2026, I have about 6,000 LinkedIn followers, nothing compared to the big business-builders on these platforms. And yet when I had less than half that, I was already working for myself successfully, posting maybe once a week and building slowly over time, complementing it with all the off-app activities: reaching out to people in my network and building business through them. So Zeina’s right to think of posting online as procrastination in a really nice outfit. It’s a head game and a procrastination trap, and she’s right to bring awareness to it.
Harry: Her actual question was really interesting: how do I know if it’s a cover-up, procrastination in disguise? It happens with anything. You could be building a website and getting no visitors. Great, then you don’t need to worry about the hex colors of your logo.
One little thing I do to help: on my iPhone, I have a “work” focus mode, and when it turns on, a quote I screenshotted comes up. It says: “If someone watched you for a week, would they believe you’re serious about your goals? Would they see discipline, effort, and consistency, or distractions, procrastination, wasted time? You don’t have to tell people what you want; how you spend your day already does.” It’s the most cold-plunge, life-maxxing influencer thing to have on your phone, and it pisses me off every day because I just want to take a break. But I keep it there, because every time something comes up, I see it and ask: is what I’m doing right now getting me what I need, which is pipeline? And if not, can I make a strong enough case for it?
Sometimes it even helps me tone things down: “you’re doing too much.” Too much activity can itself be a cover for what you actually need, which is sometimes to step away for a minute. But the point is: for any activity, content, internal ops, even working with a client who isn’t paying you enough, take a realistic look and ask whether it aligns with your stated goals. If not, throw it out.
Shaina: Zeina’s goal is to build a name for herself and use this period to experiment with getting her ideas out there. To that extent, I understand why she’s posting three to four times a week. But I’d reframe the goal, from “build a brand” to: hone my voice; connect with new people one at a time through a platform I wouldn’t otherwise meet them on; test ideas and how I pitch them in a semi-public, semi-private space. Posting and brand-building is a slow burn. It’s hard for everyone. And for Zeina, the practice of it seems to be living up to her goals right now.
Harry: If you’re telling yourself “I’m going to do three posts a week,” just ask why. “Because that’s what you’re supposed to do”? No. You’re supposed to do what drives what you actually want to happen: conversations, audience growth, or maybe just reaching out to the one person who can make a decision on something. It comes back to expectation-setting versus your goals.
Shaina: Exactly. So what’s Zeina to do? Get really clear on what she wants from this chapter and what posting will do for her. Is it new conversations with interesting people? Long-term pipeline through those relationships? Honing her voice and her writing as a new skill? That clarity is what makes this sustainable instead of a slog. Although, it is also just a slog. So here we go, climbing that mountain again.
Harry: It is a slog. Maybe make an OKR out of it, run a little science experiment. For the next month, I’m going to post this much, and let’s see what I think the results will be versus what they actually are. There’s the qualitative side, honing your voice, but also the concrete side: how does this drive new opportunities, revenue, subscriber growth, whatever it is? Just like a timeline for your business, set a timeline for the experiment so you know whether it’s worth doing.
Shaina: Well said. In Manual Override we talk about growth experiments. There’s the experiment itself, and there’s the clarity of what it is and what you want from it by when. That’s what you’re advocating: hey, Zeina, don’t sign up for three-to-four posts a week into perpetuity. Take a step back. What do you want from it by when? And can you sprint through the experiment to see what results you get?
Harry: Three posts a week over four weeks is twelve posts. That’s a lot more manageable than “build a habit of three posts a week forevermore.”
Shaina: Totally.
Shaina: Well, Harry, I think that’s Operator Hotline, pilot experiment number one.
Harry: Done.
Shaina: This was fun. I had a good time. Hopefully it was helpful.
Harry: Everyone else, call in, send us questions, and we’ll get to them.
Shaina: You can reach us at shaina@hellogeneralist.com and harry@hellogeneralist.com. And if we keep this going, maybe we’ll put a phone number on the screen for you to call in and leave your questions.
See you next time, everyone.
Harry: Peace.
Have a question about building your own independent career for us to answer on the next Operator Hotline? Comment below, and we’ll get in touch, or send it to shaina@hellogeneralist.com or harry@hellogeneralist.com.
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See you out there, Shaina
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