The patterns behind successful independents
Habits, mindsets, and common traits of the most successful fractionals, advisors, and solo-founder service businesses I know
👋 Hey, it’s Shaina. I’m back for another issue of On Work, the weekly letter on independent entrepreneurship, fractional work, portfolio careers, and more.
Today, I’m writing on the patterns I see in the most successful independent business owners I’ve encountered — the signals I use to vet people into Hello Generalist and Manual Override. I hope you’ll find it to be useful reflection tool for own business.
Lastly, a big ol’ welcome to the 16 of you who subscribed since last week — Hi! Welcome in! Help me spread the word by sharing with your friends, and please say hello in the comments.
First, a little plug for Manual Override, the accelerator for independent businesses that we’re launching this summer. We’re accepting 25 exceptional tech leaders for this first cohort, and spots are already filling up. Last day to apply is Friday, June 20.
If you haven’t checked out MO’s website in a few days, it’s worth revisiting as we update it daily with Mentors, Speakers, Demo Day attendees, and program details. This is shaping up to be an exceptional inaugural batch with involvement from some seriously special people.
If you’re curious to learn more, come attend our June 11 info session, or just reply to this email with your questions, and I’ll get back to you personally.
Now onto today’s issue.
On Success vs. Failure, and an Investor’s Mindset
Between building Hello Generalist and Manual Override, I look at about 100 profiles a week of people who work for themselves, meeting 1:1 with about 15 of them. Over the course of a few years… well, that’s a lot of people. As I chart their work over time, I’ve noticed some early indicators from the people who are most successful.
Within a 30 minute chat (or a 30 second application review), I need to make a judgement call on if I think this person will be successful working for themselves. My mindset is one of rooting for people, rather than trying to find the downsides — I try hard to take an optimistic, encouraging approach, and listen closely for the good stuff. These patterns are each small signals that add up to me believing this person is on track for a happy, future success story.
Despite my disdain of The Big VC Industrial Complex, I’ve realized there are a bunch of parallels to my work and the work investors do. Like any other new business, and certainly like early stage tech startups, there’s a high failure rate for independent businesses too.
By failure, I mean that, despite wanting to, the independent business owner doesn’t get to work for themselves anymore.
There’s a bunch of good failure states, like a reasonable person deciding that working for themselves isn’t actually what they want, or finding their way into a genuinely exciting new full-time project — I love living in a world where we can just try stuff, including starting a business, so these are very fair outcomes to me.
Beyond the reasons above, there’s some market conditions at play too. Fractional work in particular is newly popular, with thousands of people recently declaring themselves Capital F Fractional. So I see lots of curious explorers, people whose interest is piqued by the movement, and are considering it for themselves — It can be tricky to know who’s really in it or not.
And more, the full-time tech job market is *gestures wildly* a mess, with layoffs, low morale, and fewer job openings than eager candidates, so I also see lots of people just trying to make a living until they find the right full-time job.
All of these reasons give pause to hiring managers who take a chance on you, or to people like me, who stake their reputation on connecting hiring managers to committed people. Like the VCs, finding the highest quality business owners is one of the most important structural elements to my businesses:
Like an investor, I make a bet that I’m the right person to help, that our customers are the right fit for your skills and offerings, and that this is a great mutual use of our time. Unlike a VC, I’m not writing you a check (yet 😎), but I do give my time in exchange for the hope of doing real business together in the future.
In my HG seat, these patterns help me find the right candidates to vet into our marketplace, and ultimately put in front of our customers. I’m looking for people who are mentally ready to work for themselves, people who are financially ready to make contract income work in their lives, people who will not up and quit their contracts if a full-time job comes a calling. The vast majority of times, these patterns have lead me to people who keep their word, uphold the contract engagements they sign on for, and do a truly fantastic job for our customers. On a few very rough occasions, I got it wrong, placing people into fractional roles who backed out during the engagement. Failure stats on the board. Hard won lessons.
In my MO seat, we’re bringing together exceptional, high potential tech leaders who want to grow their independent businesses. My bet here is all network related: That we’ll have the right people in the batch to help each other. That they’re the right people to connect to our Mentors. That they’re the right profile to stand up during Demo Day. And as we aim to grow the program, that the people we bring into our cohort will be fabulous case studies on the other side.
In your seat, you might use these patterns as a reflection tool for where your head’s at. You might also consider them tips for positioning yourself when talking to potential customers — Because like me, your potential customers are making a bet on you too.
So if that’s failure, what does success look like? Success, is, of course, deeply personal. Your definition of success is probably different from mine, and that’s exactly how it should be. So let’s simplify it:
We’ll consider Success to mean that, if you want to, you get to keep working for yourself.
The vast majority of people get started working for themselves because someone they already knew hired them or introduced them to someone who hired them. Many of us even fall into it on accident, getting roped into a fun project, or just jumping in to help a friend.
That’s awesome. And if that’s you, you’re in great company.
The trick though is what comes next — after those first few customers.
And that’s the moment. That is the chasm that every independent business faces if they’re going to be successful. The chasm rears it’s head when those first contracts come to an end. It’s the blank-stare-into-your-laptop moment: Uh oh. What now?
People that are successful manage to traverse the windy foot bridge over our metaphorical chasm, making systematic changes to go from operator to entrepreneur. I’ll write about those in a later post, but for now, a shameless plug to share that this is the driving reason we built Manual Override.
The patterns in this list are signals to me that someone has already crossed their chasm, or that they’ll be able to when it inevitably shows up.
In the list, I use the labels Success Signal and Shaky Signal, which might feel a bit pejorative and narrow minded. Of course there’s a spectrum within each pattern, but my intention is to show the extremes.
By Shaky Signal, I mean that when I hear these things, I feel unease — it’s one brushstroke in my mental painting of someone’s success path or failure path. While I want to see the full painting emerge, each signal is an indicator.
Even very successful people give Shaky Signals at some point, so this is not to say I think that you’re doomed. We’re only human. And we’re all trying to figure it out.
The patterns behind successful independents
1. They have a strong, clear why.
Numero uno on the list for a good reason. Even beyond many of these other patterns, I look for people with a clear reason why they want to work independently, and for why they want to build their business. More, I look for people who are running toward something, rather than running away.
This usually sounds like:
Shaky Signal — Running away from a bad job: “I’m so burnt out, I hated my boss, I felt so under appreciated. So I quit that job and need to find something else. What’s fractional work?”
Shaky Signal — Can’t find a full-time job: “I got laid off, and the full-time job market is nuts, so I’m going to try and find anything I can. Can you tell me about fractional jobs? Will they just hire me?”
vs.
Success Signal — Lemons into lemonade, running toward a goal: “I’ve always wanted to work for myself, and the lay off was the kick in the ass I needed to actually start.”
Success Signal — Opportunity motivated: “There is just so much opportunity in the market for my skills that I think now is the right time to build my own thing. I think I can make more money than in my full-time job.”
Success Signal — Life change motivated: “I’m a new parent / elderly caregiver / working on rebalancing my life / interested in volunteering / etc, so balancing life and work is really important for me right now.”
So many of us have come into independent work from the Shaky Signal situations, running away from a bad job, or running out of time to pay bills when you couldn’t find a full-time job. These are genuinely tough life moments, are increasingly common, and aren’t inherently bad situations. Many successful people do in fact start here — but if you’re in this situation, I want to encourage you to think about what you want, not just what you don’t want.
What’s more, if you’re in a panicked-happenstance-entrance to fractional work, know that you’re in good company, but you’ll need to adopt the mindset of a business owner to make this work for you longterm. You’ll need to develop a why.
A strong why carries people through the hard times. It’s the motivator that will help you sit back down at your laptop in the morning after getting ghosted the day before. It’s the reason your family will still be board during the low cash flow months that inevitably happen. It’s the intrinsic, driving force that brings forth all the traits in number two.
2. They display tenacity and grit.
Courage. Resolve. Strength of character. Determination. Persistence.
You’re starting a business, just like the lore’d tech startup founders. But in an intense, slightly cruel twist, unlike the tech startup founders, you are the product. In addition to all the plain hard stuff about starting a business, starting a skills-based business can feel deeply personal.
So, I listen for a indicators of a Founder’s Mentality vs a Victim’s Mentality.
Founders show tenacity and grit. They overcome obstacles in order to get the outcome they want. They’re determined to figure it out.
A Victim might feel like the obstacles are a personal affront, and get lost on the way. They blame people or circumstances for negative outcomes, instead of taking ownership. They let the negative self talk engulf them. They resist new paths, solutions, or advice.
I think these are universally positive traits for anyone aiming to start anything, but particularly important for business owners trying to launch into a competitive market, and do it without external funding and without a big team.
Personally, hearing a Founder’s Mindset is deeply comforting to me. It’s a warm hug that tells me, This person is going to be ok! Even if this experiment of starting a business doesn’t work, this person will have a productive, happy life!
Shaky Signal — Victim of the job boards: “I just want a platform to give me a job. All I do is send resumes, and I never hear back.”
Shaky Signal — Exasperated and paralyzed by fear: “I have no idea how to find customers. / I’m scared to talk to my network. / My friends will judge me for doing this.”
Shaky Signal — Burnt out and needing a break: “I’ve been grinding for so long and haven’t ‘made it’ yet. I’m so tired of all the work politics, all the AI hype, all the tech bros. I should be successful by now.”
vs.
Success Signal — Curious and willing to ask for help: “I’m not totally sure how to figure this out yet, but I’ve been talking to xyz people to help me.”
Success Signal — Optimistic despite a tough professional moment: “I was laid off and it was awful. But it was also the wake up call I needed to finally do the thing I’ve always known I wanted to do - I want to start a company.”
Success Signal — Energized and forward-looking: “I’ve thrown myself into this! I can’t stop thinking about how I can get out there. / I stayed up all night playing with xyz tool. / Have you seen xyx article / youtube video / post?”
3. They’re aware that they’re building a business.
I want to hear some level of recognition that, in working for themselves, they understand they’re actually starting a business. Most of us don’t totally know the extent of what that means initially, so I really just want to hear some intentionality.
You might be saying — wait, success for me is serving two retainer customers, working 15 hours a week, and I already have one of them booked. I’m not actually starting a business.
And I would say to you — that’s a great goal, but what’s your plan to replace them when one churns? How will you handle taxes? Have a plan for healthcare?
Shaky Signal — Still wants to be an employee: “I just want to do my old full-time job, but work fewer hours a week.”
Shaky Signal — In a bad financial situation: “I’m going to run out of money and won’t be able to pay my bills in a month.”
Shaky Signal — Actually wants a full-time job: “I’m applying for any job I can. If I get a fractional job, that will help me pay my bills, but I’ll still be looking for full-time work.”
vs.
Success Signal — Personal life is prepped for entrepreneurship: “I’ve been talking to my spouse about this for a while, and we’ve agreed on a financial plan for me to jump start this. I’ve been stocking away extra cash to give myself 6 months to land first sustainable customers.”
Success Signal — Needs the money, but is focused: “I don’t have the savings I wish I had, but my goal is to work for myself, and I’m ready to work hard for it. I’m willing to invest in myself right now.”
Success Signal — Thoughtfully exploring: “I want to find the right next project and team, but I don’t know what that is it. I think working for myself is a great way to get there so I can meet a lot of smart people and try things out. I’m open to a full-time job if the fit is right, but I could also see myself happily working for myself, helping lots of people at the same time.”
4. They’re talking to their network, actively finding customers.
I listen for people who are sprinting into the market, rather than hiding in back office work.
It can feel really good to check the box of naming your company, setting up bank accounts, or drafting contract templates, but they do nothing to find you work, or even validate your business idea. Especially for folks just getting started, I want to hear an entrepreneurial itch: they have a great idea, a strong why, and are actively trying to sell.
This tells me they’re validating their idea with real feedback. They’re changing their mind as they learn. They’re not getting fixated on one particular path before understanding if they have willing buyers or not.
Shaky Signal — Box checking back office work instead of talking to customers: “I’m need to build my business plan, figure out my company name and logo first before I talk to anyone about what I’m doing.”
Shaky Signal — Unaware and unwilling to build a growth channel: “I just want a couple clients, so I don’t need to do any real marketing work.”
vs.
Success Signal — Actively talking to customers for feedback: “I’m spending most of my time talking to people in my network, sharing with them what I want to do, and getting their feedback. I’m also getting involved in a bunch of online groups where I can find collaborators.”
Success Signal — Actively thinking about sustainable growth channels: “I only want to support a couple clients at a time, but I’m aware that a strong pipeline is important for when one of them churns. I need to own my book of business, so I’m thinking about ways to do that sustainably. What advice do you have?”
5. They know who their customer is. Or, they may not exactly know yet, but they’re working on it.
Your offering, your ideal customer, your position in the market. Most people are rightfully clueless about all of this when they start, but the most successful people work hard to figure it out fast. They get clear on the demographics of their ideal customer, what problems they’ll solve for them, and why a customer would bring them onto their team in the first place.
Mind you, I started a business called Hello Generalist. I clearly believe that generalist skills are the future! Critical for working for yourself, really helpful for working with startups. But make no mistake: in a world where you need to stand out as the uniquely suited, obvious fit for a company to hire, you must get clear on the environments you’re best suited for. You have to face the fact that calling yourself a Generalist isn’t enough.
Clarity here unlocks a lot of things: It helps me mind meld with the skills you’re uniquely great at and the roles you’re looking for. It helps me plug you into high-converting opportunities where you have the background that matches. And it helps you chase down the exact customers you’re an obvious fit for, without wasting your time.
Shaky Signal — Mistaking their Generalist Skills as an ability to help anyone with anything: “I was employee #2 at xyz startup, so I can do anything for any early stage business.”
Shaky Signal — Very loose positioning: “I want to do marketing work for startups.”
vs.
Success Signal — Monetizing past success: “I’ve been in finance roles for 10 years, and know I can help other companies with similar work. I’m not totally sure how to package that up, but I know it will include work like managing external accountants, running a month end close, and doing ad hoc analysis.”
Success Signal — Narrowing down skills into a menu: “I’ve worked in a bunch of startup operations roles for 15 years, but there are certain skills I’m world class in. And more, I know that only some of the problems I can solve are critical to a business, vs nice to solve. I’m going to offer several things on my offerings menu, but narrow it down to the services a company is most willing to pay for.”
Success Signal — Researching the ideal fit: “I’ve talked to 20 companies, and realized that I’m most uniquely obviously suited as a Fractional Product Marketing leader for Series A - C teams who don’t have a Senior PMM function, but desperately need the layer between engineers, product, and growth. I do market validation research, build GTM plans for new products, and help teams go up market.”
Bonus patterns
While these don’t make my top 5, I get very excited when I hear these. They’re like sugar on top of the foundational patterns above.
They have what Wes Kao calls, a Spiky Point of View: I love when someone shoes up with a unique, slightly arguable, point of view about how their skillset should be applied. There are lots of Financial Services, tons of Fractional Chiefs of Staff, plenty of Exec Coaches — what makes you unique? A developed point of view is gold for framing your work around.
They are building an online audience: While internet fame is only one of many channels to find customers, building an online audience is a free, highly scalable way to build trust in a market and get in front of customers.
They are good humored, easy to talk to, and can read a room: While this one is clearly subjective, I find that people with these traits are more employable than those without it. Put simply, people want to work with people they like, people who put them at ease, people they’re excited to introduce to others.
What about people that don’t fit the patterns? Well, very few of us fit all of them. Most of the time, people are somewhere on the spectrum. How boring if we were all entrepreneur robots doing things the exact same way!
Bringing it back to how I use this list, when I’m in conflict about someone, I go back to the fundamentals: do they have a strong skillset that they’re proven in and now trying to monetize? Do I have a sense of the customer that they’re uniquely and obviously suited to help? Do I trust them?
Remember, if you’re just getting started or if you see yourself in the Shaky Signals, keep it simple, give yourself some kindness, and start slow.
I hope you found these to be useful reflection points, or tips on what to incorporate into your next pitch. Otherwise, would love to hear from you on what you’d add to the list. Jump into the comments, or send me an email.
Before we head out, 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.
Are you a startup who’s curious about fractional hiring? Check out Hello Generalist, or book a call with me here.
Are you an independent business owner who wants to grow your pipeline? Considering applying to Hello Generalist’s network, or checking out Manual Override, our business accelerator.
And check out the On Work Podcast to hear stories from the tech operators, entrepreneurs, and experts behind this independent work movement — you can subscribe on Spotify and YouTube.
Be well! Until next week, Shaina