Stories about Software


Don’t Take Freelancing Advice from Freelancers

If you’re on my mailing list, you probably saw that I just announced a new podcast on which I’m a panelist.  The title, not coincidentally to this post series, is “The Business of Freelancing.”

So what are you to make of me having a podcast that dispenses advice for freelancers and writing a blog post telling you not to take freelancing advice from freelancers?  Do I need to channel Doc Holliday in Tombstone?

Apparently, my hypocrisy knows no bounds.

Well, no, I hope.  I like to think that, after a bit of nuance, I’m right both times.  But whether that’s true or not, I can at least stake a claim to logical consistency.

Freelancers and Business Owners

In the initial post I wrote for the series, I created a distinction between freelancers and business owners.  The latter reasons about business profit, whereas the former does not.

In that same post, I also introduced this image, sketching two career paths, stating that “freelancer” is just an intermediate step along one of two roads.

Put succinctly, the freelancer either starts to reason about profit and grows a sustainable business or else they simply wind up an employee again.  I overcame the “but I know a freelancer that’s been doing it for 15 years” objection by pointing out that “employee” doesn’t necessarily mean being someone else’s employee.

In another post in the series, I talked about the duality of the freelancer’s role as an “owner-operator.”  The endless freelancer is (technically) both a shareholder and the only employee of a business that earns no profit.

But they in no way behave like the shareholder and owner, so that becomes an unoccupied, vestigial role.  They focus, instead, on the technician aspects of their employee role — delivering website wireframes or code or whatever.

Think for a moment about what this means, if you look at their role from a career advancement perspective.

The freelancer is the sole employee of a business with disinterested, absentee ownership and no plans for profit.  For any employee, career advancement depends entirely on one of two situations: business growth or changing jobs.

The indefinite freelancer can have neither possible outcome, so all that remains is perpetual employment in a dead-end business.

Advice from Business Owners, Yes, Freelancers, No

So understand who I’m talking about when it comes to taking advice.  I’m drawing a distinction between freelancers and business owners in terms of how they reason about their businesses, and their goals and aspirations.

(And, as an aside, if I’m confusing you by saying that freelancers not reasoning about profit aren’t really business owners, but then talking about their freelance businesses, I apologize.  The nuance here is that they’re technically business owners, in that they own an LLC or DBA, but business owners in name only.)

Consider the butterfly.  Like the diagram above, it has three stages to its lifecycle: caterpillar –> chrysalis –> butterfly.

Now, imagine a weird, arrested-development butterfly that hung out in its cocoon forever.  “Welp, this is great.  I’m done.”

What I’m advising is that you don’t take advice from that eternal cocoon dweller.

It’s not that all of their advice will be bad.  In fact, a lot of it will probably earnestly help you.  But some of it will be insidiously misguided, leading to endless cocooning.

And that’s because all of this advice, good or misguided, is going to orient around a cocoon-as-endgame worldview.  Aspiring butterflies will have no way to sort the helpful from the locally maximizing until they wake up one day, years from now, and ask, “hey, wasn’t I supposed to be a butterfly or something?”

Advice-Dispensing Perpetual Freelancers as Benign Expert Beginners

The butterfly analogy is perhaps visually memorable, but I want to switch gears a little and revisit something I wrote years ago.  I coined the term “expert beginner” to describe a specific archetype.

You can certainly read the post series and book if you’d like, but let’s do a quick recap.  Expert beginners are people who miscategorize themselves as experts in something before they’re competent enough to see the big picture and understand where they reside in it.

In my previous writing, I talked about the phenomenon in the world of corporate software groups.  There, it toxifies companies by casting an incompetent as the unofficial leader.  Poor decisions, internal friction and attrition all ensue.

But if you remove the tight group constraint, the pressure cooker dynamic goes away.

In other words, imagine an expert beginner as a solo-operating free agent.  Overestimating one’s own competence still has consequences, but those consequences won’t involve demoralizing and frustrating others.  Instead, this unjustified self-assessment will just put the expert beginner on a laboring gig treadmill.

Any perpetual freelancer is, at most, an advanced beginner at business.  Advanced beginners in a discipline can recognize some “aspects” of a situation and throw “recipes” at it.  But, like the permanently-cocooned pupa, they lack broader, universal context of what business ownership actually entails.

(Here’s a blog post that talks conversationally about the various Dreyfus stages, if you want to read more.)

At this advanced beginner stage, they can work their way to the “competent” stage by starting to reason about and grok profit and business models.  Or, they can move instead to the expert beginner stage, where they conclude that continuing to pay the bills freelancing for a few years qualifies them as “freelancing experts,” qualified to give business advice.

The Trouble with So Much Freelancing Advice

What’s so wrong with this advice, then?  Can’t an advanced (or expert) beginner teach a novice?  Doesn’t teaching sixth grade math just require someone to have passed sixth grade math?

In a lot of cases, the answer might be yes. But not in this specific case.

The world sells an aspiring freelancer a certain bill of goods.  As of the time of writing, here is what Google shows you when you ask it “why go freelance?”

Probably the most common call to action for freelancing is the iconic, “be your own boss!”

This snippet certainly captures that spirit in spades.  Rely on yourself, decide what meetings to go to all on your own, and by God, be a stronger person.  You boss babe/dudebro, you.

There’s just one little problem.

All of this stuff is true of the shareholder/owner — not the employee.  And recall that the perpetual freelancer has abdicated the role of shareholder to focus on being an employee.

This creates a dynamic where the novice freelancer sets out on the path to become the boss — the shareholder.  But the freelance expert beginner shares with the novice a detailed playbook for how to operate forever as an employee.  And an employee of a stagnant business at that.

Most freelancing advice teaches you how to fail to get what you ultimately want out of freelancing.

Expert Beginner Freelancing Advice: Detailed Examples

Instead of hand waving at this, I’m going to offer a bunch of really detailed examples to drive the point home.  In researching topics for our podcast, I’ve consumed a LOT of freelancing advice on a lot of sites, podcasts, and Youtube channels.

And reading it has made me bang my head against my desk.  At times, literally.

So let’s look at a bunch of takes on common freelancing situations through three different perspectives:

  • Novice: someone considering taking the plunge or who has just done it.
  • Expert beginner: a long-time freelancer selling hours, never having earned a profit.
  • Proficient: a business owner (solo or otherwise) that reasons about and seeks to improve their business equity and profitability.

As we walk through these examples, I’m going to spend some time explaining why each is so frustrating to me.  The thought of the expert beginner giving the novice this advice makes me want to throw things at my screen.

And, for each one, I’ll also offer a contrast in the form of what the expert beginner advice would actually look like from a shareholder/CEO’s vantage point.  And I want to drive home how the expert beginner advice optimizes for the employee experience, rather than the business owner’s.

1. “Giving Away Time” on Sales Calls

  • Novice: “A prospect wants to have a sales call and pick my brain about strategy, and he booked a few hours with me!”
  • Expert Beginner: “I’ve learned that lesson, and I tell prospects that I start a clock if they want more than half an hour because time is money.”
  • Proficient: “High ticket sales, like custom app dev, require a lot of time investment on my part. I need to learn to separate tire kickers from legitimate prospects on my own dime.”

Issue with expert beginner advice: you’ll suffer false negatives in your sales process and discourage repeat business by nickle-and-diming legitimate prospects with legitimate sales questions (and you come off as desperate).

When you sell application development, make no mistake.  You sell a high ticket item.  Your labor has a market rate of at least $10K per month.

And the more expensive something is, the longer and higher-touch the sales process.  When you buy a car, you typically have multiple in-person interactions with sales people.  It’s not a 90 seconds of shooting baskets at the Pop-a-Shot for $2.

The expert beginner, with this advice, is telling the novice to pivot from a 5 figure sales approach to a 2 or 3 figure one.  It’s like telling a car salesman to stop letting people test drive for free and to charge them $10 for a spin around the block.  Congratulations on this business shift from selling Jaguars to hawking carnival rides.

You can solve the tire-kicker problem in a way that doesn’t devalue your offering and make you look like a carnival barker to serious buyers.  When you have a high ticket offering, an enthusiastic book of business is your life blood and leverage for future work.  Pissing them off immediately makes your work transactional and puts you on a gig treadmill.

Looking at it From a Business Owner’s Perspective

Imagine yourself as owner and CEO of a service business.  You’ve grown enough that you hire someone to handle sales for you.

One day, your sales guy mentions that, until recently, a lot of sales calls had just been going nowhere.  Excited, you asked him what changed to improve the situation.

“Well, I’ve actually started demanding money from prospects if they want to get on a sales call.  Now I have way fewer sales calls, and when people do talk to me, they know I’m important.”

As the owner of the business and CEO, is your response to this, “atta boy!  Good thinking!”  If it is, I suspect your sales guy also has some magic beans that might interest you.

Sales and account strategy are two separate business functions.

And if the only thing standing between 0 and your prospect grokking your entire strategy deliverable is a billable hour , your “strategy” sucks anyway.  How would you feel about a lawyer that cleared her throat, started a timer, and said, “I would strongly advise that you not commit murders, invoice to follow.”

2. Outsourcing Tasks

  • Novice: “Outsourcing eats into my pay; why would I pay someone to do what I can do myself?”
  • Expert Beginner: “Man, I hired a bookkeeper to keep track of expenses and send invoices, and it was totally worth it because I hate that stuff.  Now I can focus on my super power — app dev.”
  • Proficient: “I will outsource a task when I project that the revenue I can bring in with my freed time is greater than the cost of outsourcing the task.”

Issue with expert beginner advice: you risk wasteful spending purely on the advice of someone who has anecdotal feels that their own spending wasn’t wasteful.

On this one, I actually empathize hard with the expert beginner.  I have, in the past, blurred the lines between business and personal (lifestyle business) when it comes to outsourcing tasks that I hate.

But understand that hiring help to do something because you don’t want to do it is a personal decision — not a business decision.  Hiring someone to do your books or redesign your website without building a business case for it is no different than hiring a cleaning service to clean your house because you don’t want to spend time doing it.

Looking at it From a Business Owner’s Perspective

Back in the CEO’s seat imagine that you have enough app dev business to make a full time engineer hire.  She’s great at engineering, but one day, she says to you, “you know, keeping up with my inbox and JIRA and stuff really isn’t my super power.  I’ve hired an administrative assistant to really free me up to be awesome — you’ll see his invoices start coming through next week.”

Would you just shrug and say, “seems legit?”

Of course you wouldn’t.

Hopefully you’d never be in this cartoonish position in the first place, but if someone did approach you to make this request, you’d want to see some kind of business case — some specific proposal as to exactly how that assistant’s help would generate more savings or revenue for your business than the cost of that service.

3. Answering RPFs and Rate Structures

  • Novice: “If I offer a low, flat price instead of an estimate, I win business!  (Wow, I hope my estimate is right or I’ll lose money.)”
  • Advanced/Expert Beginner: “Flat pricing is for suckers.  Answering RFPs with time and materials estimates is what professionals do.”
  • Proficient: “Buyers HATE time and materials, so give them a flat price that bakes in plenty of buffer above your own cost.  That will make you much more expensive, so you need to position yourself to justify the price.”

Issue with expert beginner advice: freelancer time and materials is a zero-profit model.  The expert beginner is basically offering you their “100% profit prevention, guaranteed” formula.

One theme that comes up a lot with freelancer developers is what I’ll call found leverage.  You start out desperate for work — any work — to get going.  In that sense, it’s actually pretty similar to being an entry level job seeker.

Get a few projects under your belt, however, and you start to feel a shift at the negotiation table.  Each time you sit down at it, you understand that you do have options.  You can tell a prospect “no thanks” without worrying about paying the bills.

Flush with this newfound leverage, freelancers start to disqualify prospective business as demand for their services increases.  But they disqualify business in a fairly capricious and employee-lifestyle maximizing way.  (This has a number of ramifications, and if this post doesn’t get crazy long, I may touch on a few of the other ones.)

In this case, they use the leverage to force clients into agreeing to their lazy pricing scheme.  The novice astutely perceives the business-savvy situation that they’re a budget brand, so they should undercut competitors on pricing and price in a way that makes clients happy.

The expert beginner tsks the novice, advising them that if they elevate their brand to “still commodity, but slightly less budget,” they can use their newfound leverage.   Taking this advice, novices still have to undercut commodity competitors on price, of course.  But they now can use their leverage to optimize their still-budget rate structure for client misery and minimized freelancer risk.

In other words, the expert beginner’s advice on rate structure is, “get enough demand for your services that you can ensure you get paid for every minute on the keyboard, even if it bankrupts your client, which is a ‘them’ problem.”

Looking at it From a Business Owner’s Perspective

From a business perspective, a rate structure that makes projects a zero-sum game against clients is really just a positioning problem.  And hourly billing is kind of incumbent, so a lot of clients will just sigh and put up with it.

But, let’s look at this one from the shareholder’s view.  Recall that the only path to profit for an hourly billing agency is to buy contractor/employee person-hours and then sell them to others at a mark-up.  So, as the owner, I kind of have two choices here if the sales group is trying to figure out what rate structure will win business, while reducing risk of overrun.

  1. I can go with the custom app dev agency flow and sell person-hours, recognizing that this creates a dynamic where I need to claw every dollar of my profit from my employees’ potential wages.
  2. Or, I can create better positioning and offer packaging to charge a premium, flat rate.  This gives me way more efficiency/cost savings (and profit) levers than depressing staff wages.

As I mentioned in the linked blog post, marking up hours is nonsense for a solo freelancer (which is why the solo freelance hourly model is zero-profit on its face).  So, as the shareholder, this one just becomes a question of “do I want a business that earns profit, or not?”

The expert beginner is urging you to go with “not.”  As a business owner, I’d counter by slamming my face into my glass desk on your behalf.

4. Setting an Hourly Rate

  • Novice: “If I go too high, I’ll chase away business.  Does anyone have a formula, like divide your annual salary by $100.”
  • Expert Beginner: “Just charge more, you’re worth it!”
  • Proficient: “If you’re serious about owning a business, stop selling hours of labor.”

Issue with expert beginner advice: Same issue here as the last one, cropping up in a different way.

I’m not going to link and put anyone specifically on blast here, but this is a screenshot of some freelancing advice that I saw somewhere.  The part I circled captures the issue most succinctly of any of the (many) sources where I found advice like this.

The part about reverse engineering your hourly rate based on what you want to make (and your expenses, of course) is sort of evocative of the way MLMs and other scams get people in: “you decide your own pay!”  But it’s really just the logical conclusion of pricing on the basis of “how much do you value yourself?”

In a way, I actually like this because it’s the most honest possible take on how to decide your hourly rate: make up a number based entirely on your ego.

As software developers, I’d argue that we’re uniquely vulnerable to this siren song, since we collectively toil away in a heavily gamified environment where Stack Overflow points, CoderJousts hit points, and other units of carnival cash matter to a comical degree.  Your freelancer hourly rate is as much about pointless &$%# measuring as about business.

So of course the expert beginner is boasting, “just charge twice your rate — I did! (psst, hire me, someone reading, since you can now see I’m a level 80, $200/hour fire-wizard on Upwork!)”

I don’t want to get sidetracked from this already-monstrous post and start talking detailed pricing theory.  Here’s a very brief (and well articulated) primer if you want to start tugging that thread.

Looking at it From a Business Owner’s Perspective

A business owner looks at expert beginner developer freelancers with what I’d probably call sympathetic bemusement.

Selling app dev hours is “competitive pricing,” full stop.  Your goal is to undercut your competitors, even when your hourly rate is higher.

If you don’t believe me, think of what you say when people balk at your hourly rate: “but it’ll take me less hours and, like, be better quality or whatever!”  You’re just telling the buyer that you’re cheaper in the long run.

A business owner views freelance app dev (modulo stack and freelancer cost of living) as a commodity within a fairly narrow band, identifiable by the fact that you’re charging an hourly rate near their imagined rate.  In other words, they already think “‘Rails Dev in the US’ is worth about $130 an hour to me.”

If you tell them $140 or $120, instead, they’ll probably shrug and say “whatever, fine.”  If you tell them $50, they’ll ignore you because they don’t want crap labor, and if you tell them $250 they’ll laugh, tell you to keep dreaming, it’s cute, and also ignore you.

What neither the expert beginner nor the novice understands is that your hourly rate, combined with the fact that you bill hourly, combine only to determine what shelf in the grocery store of commodity labor the clerk places you on.  Buyers then come along and buy you as a commodity, based not on your worth or anything about you, really, but based on their established budget.

So, sure.  Double your rate or whatever.  I don’t care what your rate used to be.

As the business owner, I’ll pay your rate, provided the random number you assigned yourself and then doubled falls within a standard deviation of the actual market rate of your commodity labor.

5. Acquiring Business

  • Novice: “I’m not sure how to go about getting my first clients; it seems daunting.”
  • Expert Beginner: “Get on Upwork, Toptal, et. al, grind, grind, grind and get better at applying as you go.”
  • Proficient: “Create a marketing and sales funnel with specific processes that you control.”

Issue with expert beginner advice: relying on a marketplace as your business acquisition platform positions you as a rental employee.

I hope that Niall values a follow link enough to forgive me for showcasing this blog post the way I’m about to.  But go read it, because this is a guy who hires people on Upwork (but I guess also sells his own stuff there or something).  Anyway, I’m not really clear on what he does, but what I am clear on is the process for evaluating freelance web developers that he lays out.

Here’s what he thinks of self-proclaimed “FrontEnd Developer (React, React-Native, Redux, Firebase),” Hassan.

Sorry, Hassan.  You may be 1337, but your grammar sucks.  No business for you, sir.

If you’ve spent time as an employee, this should look familiar to you.  Some random evaluator randomly nitpicking unrelated bullshit has a tried and true place in our society: the job interview process.  Hassan, is not, in this interaction, a vendor; he’s a job applicant.

So understand what the expert beginner advice here really entails.  It’s telling you to get really good at the application and interview process required of employees.  But, in a sort of perverse irony, this particular advice casts you not even as the sole employee of your own business, but basically just a prospective employee of Niall or someone like him.

Looking at it From a Business Owner’s Perspective

Back in the CEO’s office, imagine your ace saleswoman wanders in and shares with you her new business acquisition strategy.  You’re intrigued.

Is she going to tell you about some new social media strategies for the advertising budget? An overhaul to your landing pages and better copy on the services page?  A plan to attend some virtual conferences and line up speculative lunches with tech executives?

No, it’s none of those things.

Get this.  I’m going to create an Upwork profile, which is awesome because it requires very little up front work or knowledge of sales for me to get started.  Then, we just sit back and wait for Niall to evaluate my grammar!

What do you think, boss?  Is Upwork a good play?

I don’t know about you, but I’d tell her, “yes, it probably is for you and your new, post-employment freelancing career, which just started 4 seconds ago.”

In all seriousness, you might be able to generate introductions and business via platforms like Upwork, and you might even be able to parlay that initial business into a situation where they view you as a partner and not a commodity laborer, needing to demonstrate good grammar and enthusiasm for Niall.  But understand that this a SERIOUS uphill battle, when you’re using a platform that screams “I’m a commodity laborer that can’t figure out my own sales and marketing.”

Sure, look for gigs on places like this to pay the bills if you’re in a pinch.  But, for the love of God, don’t aim to get good at it.  Get good at your own sales and marketing.

What is Worth Listening To?

I’ve spent a lot of time eviscerating large cross-sections of the freelancing advice you find on community sites, YouTube channels, podcasts, etc.  It’s been fun and cathartic.

After several months of looking for good topics for the podcast (that and SEO are my contribution to our split of responsibilities), all of this maddening advice had bottled up a frustration in me that needed venting.  And, believe it or not, I could have written twice as many examples, easily.

But let me stop that for now, and work toward a conclusion on a more positive note.

Not all advice you get from freelancers, even the expert beginner variety, is bad.  To circle back to the earlier metaphor, some perma-cocooner wisdom is bad, in that it teaches you how to be a perma-cocooner.  But some is solid, in that it does walk you through caterpillaring and building cocoons in a way that leads to butterflying.

Let me briefly walk you through good advice that I see from these folks:

  • Do your diligence on bookkeeping and taxes.  You need to get good enough at this to manage someone else doing it when the time comes.
  • Build a portfolio or some other way to showcase your previous body of work.  This is what will become your sales collateral as you become a business owner.
  • Set boundaries with clients.  As you grow and refine your business, you, not the clients, will increasingly dictate what working with you looks like.
  • Try for a deposit or partial/total payment up-front.  You appreciate the risk-reduction already, but, later if you grow, you’ll appreciate what this means for your business’s cash flow, as opposed to your personal checking account.
  • Create an entity, like an LLC and set up separate business bank accounts.
  • Don’t negotiate on price.  Established, profitable businesses don’t negotiate — employees do.  You can offer things like volume discounts or differentiated pricing schemes, but no negotiating.
  • Try to niche down.  Unless you go the agency route, and kind of even then, niching is the only way to build business leverage and equity.
  • Don’t under-value yourself.  But don’t stop at the advice to raise your hourly rate.  Having an hourly rate at all and looking for business on commodity sites are both additional forms of under-valuing yourself.

How to Know Where to Look for Advice and Where Not To

And, finally, I’ll close out with something designed to help you widen the net as much as possible in your business ownership journey.  There are plenty of people out there to listen to, and knowledgeable ones at that — more knowledgeable than me, certainly.  The trouble is that those people typically aren’t trying nearly as hard to reach you as the hucksters are.

In a great post about the dream of business ownership, Dan Andrews says this about lifestyle design, the Tim Ferris school of entrepreneurship.

Less than 1%* of lifestyle designers make their money by selling eBooks and courses on how to be lifestyle designers, travelers, mobile business owners, or similar.

People often sell freelancing to would-be freelancers as a certain form of lifestyle design.  And the same wisdom applies here.  The overwhelming majority of people who succeed at freelancing and graduate to equity-producing business ownership don’t turn around and create a new business teaching people how to copy their blueprint.

Why would they do that?  They already have successful businesses.

Be Very, VERY Skeptical of People with “How to Freelance” Type Info Products for Sale

And that leads me to my first piece of advice here.  Be very, VERY skeptical of anyone selling you a “how to crush it freelancing” video bundle for $399 can you believe it only $29 for a LIMITED TIME!

There’s a common entrepreneurial anti-pattern that happens with people whose main and exclusive vision is “ditch the 9-5.”

  1. Go off on your own as a freelance web developer, or whatever.
  2. Have limited, if any, real success with that.
  3. Discover the attraction of digital info products as a source of passive revenue to supplement your spotty freelancing and help pay the bills.
  4. Think, “gosh, but what do I really know that I could teach people?”
  5. Think, “wait-just-a-gosh-darned-minute, I’ve been freelancing and reading all of these books about how to freelance, so maybe that’s the ticket!”
  6. Experience brief, conscience-driven cognitive dissonance when you realize you’ve never actually, succesfully done most of the things in the instructional video you’re building.
  7. Power right through that with, “but I have read a lot about it, and I might even cite some of those people from time to time!”
  8. Profit!

Don’t worry too much about karma here.  The dustbin of history is littered with the dozens of people per month who think they’re an early mover on this game.  But, for the love of God, don’t take advice from this person before they go out of business.

Now, let me be very clear about something.

There are valuable pieces of information out there about freelancing, and not everyone with an info product or coaching offering is a huckster or amateur.   It’s just that the signal-to-noise ratio is so low, like the things in your spam folder, that you’re probably better off just not going there and living missing out on the the occasional false positive.

I would personally make it your default to avoid people with websites about helping freelancers, and especially things they’re trying to sell you.  Consider this segment guilty until proven innocent, if there’s even the whiff of a profit motive.

And this is doubly true if they try to sell you on freelancing itself, talking about lifestyle perks like setting your own hours and working from home.  They’re hawking an idyllic lifestyle to prime you for a cash grab, much like an Amway salesman.

Default to People with No Skin in the Game

If you’re wondering where I fit in and are thinking back to my initial Doc Holliday quote about hypocrisy, understand that I own a content marketing business and have created a handful of miscellaneous books and Pluralsight courses.  Not one of those things has anything to do with freelancing.

I have never earned a cent from giving advice to would-be freelancers and I have no plans to, either, unless we eventually monetize the podcast.  And, if we did that, it’d be beer money.

I’m in it just because I enjoy sharing my knowledge, sandwiched in between rants.  So, as table stakes, you can rest assured that what I offer is honest opinions based on experience, with no motivation to make it weird, somehow.

So, even if you must listen to perpetual-cocooners, at least listen to ones that are just sharing their experience (business ownership advanced beginners, as opposed to expert beginners), such as it is.  Anyone, including me, doing this, is at least doing it in good faith, whatever the quality of advice.  That’s a good default rule for filtering advice.

Consume or Buy Content from Freelancers With a Proven Track Record: Those Who Have ‘Graduated’ to Business Owner

Now, moving past that, let me speak a little to folks who are building an audience, marketing to, or selling to this segment that are legit.  I’m going to give you a list of people I know that is, of course, non-exhaustive.  But I’m hoping that giving you some examples drives home the pattern.

You want to look for people that have a proven, long-term track record of success and expertise on the subject.  Think of freelancers that built agencies, or semi-retired folks looking to create a lifestyle business purely for personal reasons, or freelancers that shared so much content for so long that people were actually coming to them, asking for coaching or books.

Here are some examples of people that you can follow, who I’m curating on the basis of personal interaction and experience.

  • Matt Inglot, who built and has owned an agency for years, created a popular podcast, and provides a lot of content.  (I honestly don’t know if he even sells anything to freelancers or if it’s all just free).
  • Jonathan Stark, who had years of agency experience, then consulting experience, all the while having strong opinions about pricing and a growing following on the subject.  In recent years, he’s turned that organically built following, by its demand, into a business.
  • Philip Morgan, who helps indie consultants with positioning.
  • Kai Davis, who helps with leads and marketing services.

There are a couple of common threads here with these folks, which you can further generalize in your travels.  First, they all offer more specialized service and expertise than “I’ll teach you to freelance.”  And second, all of them give away a TON of free value, asking for no reciprocity, and have done so for many years.

Look to Business Owners More than Freelancers

One final bit of advice to close out, and to bring this all full circle, and back to the theme of the ongoing post series.  Look for advice from folks that are business owners, rather than freelancers.

This isn’t the most straightforward distinction to make, given that I’ve defined the difference as reasoning about profit.  I mean, if someone has an agency or a business that employs multiple people, they’ve obviously made the jump.  But there are plenty of solo business owners (and not “just” freelancers).  To tell the difference, here are some questions to ask:

  • Do they sell something more than just person-hours of their labor?
  • Can you find some kind of offering ladder on their site?
  • Do they have productized services or clearly defined ways of engaging and working?
  • Are they actually working with and managing other people, or is the “we” on the website a lot of sound and fury?

That’s a decent, but non-exhaustive, list of things to look for.

So avoid the hucksters, look for established people, and, in general, try to consume the experience of business owners in general.  That could mean someone like me or others who have “graduated” from freelancing, but it might also mean founders of SaaS companies or what have you.

Where you want to head is having a valuable business.  Freelancers don’t have that, so make sure you take advice instead from people who do.

(**One final editorial aside to illustrate that I’m not coming from a position of negatively or hostilely judging freelancers in general.  If you go back 5+ years, to when I was freelancing, and you scour my social media and this blog, you will almost certainly find younger me giving what I would now consider misguided advice.  The issue isn’t so much with the people dispensing the advice as with the commodification platforms that have, in recent years, cast freelancing as basically wage employment with different paperwork.  But that is a topic for another day.)

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3 years ago

This is a great read! Plenty of information to digest. Thank you for the time and effort that went into it!

Erik Dietrich
3 years ago
Reply to  Luis

Sure, it’s fun for me. Thanks for reading and for the feedback/kind words.

3 years ago

I still can’t get past the term “zero-profit”. I know this is how quite a few freelancers handle their accounting but that’s part of the problem. The whole point is to build capital / equity on which to build your business. If you spend it all (while realizing how much you can deduct as a business expense) you deprive yourself of choices later on. Another thing: In my experience, I hardly ever deal with business owners who might be more open to a value proposition. I deal with employees, and this applies up to the C-Level. People who don’t have… Read more »

Erik Dietrich
3 years ago
Reply to  Nils

I don’t think stake in the business is relevant for wanting or not wanting hourly bids. I’ve logged time in management in corporate employment, and I didn’t like hourly bids there, either, though they were tolerable if I could sell superiors/the rest of the business on the idea that there was no other way. But no one _likes_ it. Nobody enjoys the unbounded risk of writing a blank check, which is what hourly billing is. It’d just be a question of whether you were accountable for a budget or not. For instance, if a director at some mid-sized company is… Read more »

Last edited 3 years ago by Erik Dietrich