Sorry, Offering To Work For Free Is A Really Bad Strategy (But Not For The Reasons You Think)

There is the conventional wisdom about how to get a job: Go to school. Get a degree. Send out your resume. Get hired and work your way up the chain.

Then there is the unconventional wisdom. You see this expressed a lot online. They say that the easiest way to break into an industry when you’re starting out is to find someone you admire and offer to work for them for free. Everyone from Gary Vaynerchuk to Ramit Sethi to Charlie Hoehn has recommended free work as a potential strategic move in one’s career.

I’ve given this advice myself. I’ve lived it myself. It’s how I became a writer. It’s also how I eventually ended up with a gig as the Director of Marketing at American Apparel in my early 20s. But as someone who is now flattered to be inundated with requests from young men and women offering to work for me for free, I can say without hesitation: Emailing people you admire and offering to work for free is a really bad strategy. It’s almost as bad as blindly submitting your resume and hoping to get hired.

I’m not saying that to be a contrarian. I’m not saying that as someone who got lucky and is now trying to discourage other people from coming up behind me. I’m saying you’ve been sold an incomplete map and that’s the reason it’s not working for you.

To show you what I mean, I searched “work for you for free” in my email right now and am posting the first thread that came up. It’s from a young kid whose name I am redacting.

From: __________

Subject: to work for you for free

My name is _________, Im 20 years old, and will work for you for free.

I love to read, and your latest book “Ego is the enemy” made sense, so that’s why I’m emailing you.

I’m hardworking & motivated.

Hope this reaches you.

Obviously he means well and obviously I appreciate the offer (and frankly, it’s something I never dreamed would happen to me). Even so, I’m not going to be hiring him…even though I was hiring at the time the email came in. The worst part is that when I get an email like that, as much as I appreciate it, I’m probably not going to take the time to explain why emails like that don’t work. I’d love to, but once I’d start, I’d never stop.

What the “Hey, I’ll work for you for free” approach misses is a fundamental reality of the marketplace. It assumes that price is the reason that people are not beating down your door offering things, but that is almost certainly not the case. They’re not hiring you because they can afford not to.

What do I mean by that? Very rarely do busy or successful people have a set of undone tasks where the main impediment is not wanting to pay (or not being able to afford) for them to be done. What successful, busy people would rather not pay for is taking chances on people and all of the training that that entails. Erasing wages from the equation does not eliminate the risk and cost of hiring someone. I wish it did, but it doesn’t.

I’m not simply knocking this striving kid’s logic. I believed it myself. This naïveté is also the reason most of my emails went unanswered when I was 19 years old.

What I should have understood—what most people don’t understand—is that the impediment for entrepreneurs and executives is usually not money: It’s time. It’s trust. It’s lack of skills. It’s the opportunity costs.

The economist Tyler Cowen wrote about this in Average is Over, a book about the future of work and technology in America.

It doesn’t matter how flexible the wage is in the more complex, less brute force jobs. A manual worker who just shows up at your door is probably not someone you want to hire unless it is already part of a preexisting business plan with broad buy-in from your enterprise and your creditors. The worker might say, “I’ll lower my wage demands by thirty percent!” or, “I’ll work for nothing!” It usually won’t matter. The sad reality is that many of these workers you don’t want at all, even if the business plan involves additional labor. Some workers simply aren’t worth the trouble unless the demand for extra labor is truly pressing.

It took me a while to get this. I sent a lot of emails but rarely got responses. It wasn’t until I was was a college sophomore and looking to break into writing, and I emailed Tucker Max that something different happened. Mostly, it was my approach that was different. I didn’t say: “Duuude, I love you, please let me work for you and you don’t even have to pay me.” In fact, it wasn’t until we communicated a half dozen times that I even broached the subject of being hired. Those first emails served as a way to pass the most crucial test (that I wasn’t crazy or weird). After I had passed, I sent him an email that said, in effect, “I noticed that you have a lot of unsold advertising inventory on your site. I have an idea for how to make use of it, would you let me try?” It was based on this email that he gave me a shot and that shot eventually turned into a job and then the businesses and writing career I’ve built since (as well as a mentorship that shaped me as a writer and person).

I had picked something specific, that’s what allowed me in the door. Even so, I didn’t fully understand that that was what happened. A year or so later, I was able to meet the author Robert Greene through that position. At lunch, Robert mentioned that he was having trouble finding a research assistant. I had to restrain myself from leaping across the table, so I just said, “Please, please let me work for you for free.”

Robert responded, “Nobody works for me for free.” Instead, he gave me a test. He needed some interviews transcribed. He would pay me to do them and then, if I did a good job, there might be more opportunities.

As I have developed into my own career, I see now how lucky I got both times. The lesson to take from my experiences was not, “offer to work for free.” On the contrary. The lesson is: Find somewhere and something where you can add value. Not generally, but specifically.

If you ask most entrepreneurs, they will tell you how overloaded they are. Why don’t they hire someone to help? Because hiring someone is itself a burden. The looking, the interviewing, the assigning, the training—these responsibilities often cost more than leaving the tasks undone. Letting a stranger into your organization—especially a smaller organization—is stressful. It risks not only not panning out, but potentially disrupting the flow you already have.

When someone says, I’ll do anything, what they’re often unwittingly telling their dream employer is You’ll have to teach me everything. That’s why they don’t get the shot they so desperately want. They’ve made it seem like too big of a gamble.

For the same reason that investors are actually suspicious when companies too willingly offer up equity, or that seasoned consultants see a red flag when a client dangles “a percentage of the potential profits” as their form of payment, most employers don’t want free work. Because it costs more than you think. Conversely, when Sheryl Sandberg got raked over the coals for putting up a free internship for the Lean In Foundation, she wasn’t trying to save $9 an hour—I can assure you of that. She was willingly offering to absorb the cost of bringing someone on and training them. But, again, most of us aren’t running charities.

So that’s the paradoxical position that applicants looking to break into an industry face. They want to be given a shot, but don’t quite understand what they’re asking for. They haven’t bothered to actually put themselves in the position of the person they are looking to work for and thought: “Where can I contribute?” “What’s a way I can showcase my skills that imposes the least?”

This is how Bill Belichick got his job working for the Baltimore Colts, for example. He offered to watch and break down film for the team and volunteered to do it for free. He didn’t say: Give me an office. Give me a couple players to work with. He didn’t say, let me travel with the team. He picked a niche—a niche that didn’t interfere with anyone else’s job and even better, it was a niche where his contributions could be very easily evaluated. (Was he finding things that helped the coaches do their job? Yes or No?)

In retrospect, this is what was flawed in my offer to Robert Greene. A research assistant is a tough job which requires an incredible amount of upfront explanation from the author. The last thing he wanted to do was onboard me and then find out I sucked. But transcriptions? That was easy. For $100 or so, he was able to see what I was made of. I, in turn, was able to learn a lot about the project by osmosis—stuff he not only later didn’t have to explain to me, but in showing that I could learn by osmosis, I was again, proving myself.

When you understand that this is the position that the people you want to work for are in, it’s much easier for you to figure out how to approach them. Let’s say you want to work for a writer and you notice that their posts have typos in them—send a friendly email pointing them out whenever you find them. If you know video editing and see that someone is beginning to experiment with video, volunteer your services. If you want an in with a busy executive, offer to create a morning read of news and analysis for them. If you want to connect with someone running an influential podcast, you can regularly send a list of suggested guests and explaining why they are a great fit for the show—it is an easy way to see if you are operating on the same wavelength as the other person. If you wanted to be a coach or a consultant, find videos of them online and come up with feedback or tips you could send over that prove that you know what you’re talking about—and then ask if they have anything else you could look at.

It’s like a date. Nobody wants to commit to a three day road trip at a start of a relationship—what if it’s horrible? How will you get away? But coffee? A dinner? These things have plenty of exit opportunities. Plus, you were going to drink coffee and eat anyway!

So instead of looking to just get hired, the key is to find something to do that’s small, finite and quantifiable. It’s also important to understand that coming up with this is your job—that is, if you want the job.

Is that unfair? No. You’re the one soliciting a job. If you’re going to knock door to door as a salesman, you better have a good pitch. You better understand that optics are everything. You better learn that imposing is the fastest way to turn someone off.

Willing to work for free to prove yourself is a great little distinction. But it’s worthless by itself.

Now, what if one had skills, had come up with the perfect arrangement and was willing to work for free?

Well, try it. (But please, not with me. I’m staffed up!)