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I’m a big fan of “free work.”

No, I don’t mean doing favors or giving handouts. I mean a deliberate process of forgoing immediate earnings to gain experience, knowledge, and credibility.
What sounds controversial to some was the dominant path people took to building careers for hundreds of years.

An experienced professional, often in a trade or art, would take a mostly inexperienced young person who worked for free or for very cheap and through that process, learned to become successful himself.
It wasn’t a teacher/student relationship but a master/apprentice relationship. There was no classroom time or homework, but learning and growth happened all the same.

I’ve beaten the free work horse over and over again on this blog and elsewhere. My story building a career after I dropped out of college depended heavily on free work.
My job at Praxis even started with a free work proposal.

Over the years as I’ve begun working with more young professionals, free work has been the most reliable way for them to land opportunities to work.
Why? Let’s do a recap of the primary value of free work:

  • The expectations bar is lower. This means you can underpromise and overdeliver.
  • It costs the business owner very little or nothing, meaning they can afford the risk.
  • It allows you to prove your value up front — this opens up positions for you that might otherwise be closed because of your experience level.

I’ve seen people use it to get their foot in the door at an entry level job and quickly grow into a position that would require years to get. People from Bill Belichick to Ryan Holiday have built their careers off this.
But the thing is, there are far more failures from people doing free work than there are successes and the reasons for those failures need to be addressed. Free work is NOT a golden ticket, and it is by no means easy.

There are things people do to mess it up all the time.

1) You don’t make a clear proposal.

At a conference earlier this year, I had a student approach me after my talk. During the conversation, he said this:

“I loved your talk and what you’re doing at Praxis. Can I work for you? I’ll do it for free, and I just want to be involved.”

Obviously, he means well, and I appreciate the offer but what I heard when he said this was “can you do me a favor?”

Then a series of questions go through my head.

  1. What does he want to do for me?
  2. What can he do for me?
  3. Is this going to be a distraction? Am I going to have to manage him and teach him?

This kid assumes incorrectly that price is the reason I haven’t hired someone like him. It’s not price. I’ll spend anything for a good employee. The reason I haven’t hired him is because I have no idea what he can do for me yet.

Contrast what he said with a better pitch like this:
“I loved your talk and what you’re doing at Praxis. I’d love to start taking photos and videos of your other talks. I can do the first few for free, and I think you’ll get a ton of value of putting them on YouTube and the blog. People need to see this.”

Now I know what he wants to do and I would have said yes in a heartbeat.

(Here’s a solid template you can use)

The lesson here is that free work is an added value. It’s not the primary. Nobody will hire you to work for free if they don’t know what you’ll be doing. You still need a value proposition.

2) You set unreasonable expectations.

The opposite of the above is to give yourself too much to do. You set unreasonable deadlines. First, you give yourself tasks that you can’t deliver on. You get the employer excited to work with you, and then you disappoint.

This is an almost guaranteed way to ensure your work experience fails. You’ll create ill will on both parties, and stress yourself and the employer out.

Be honest with yourself and the employer about what you can do. Also, be honest about what you’re even willing to work on. Often when we’re working for free it’s easy to become bitter and lazy because we think we’re doing too much, even when we’re the ones who set the expectations.

A new part-time worker at Praxis, Laurie, provides a good case study on this. She gave me the exact hours she’d work in advance and told me straight up that she wouldn’t be able to deliver on one of the tasks I wanted her to do.

She’s gotten all her work done and even some extra when she has time, and she’s done it in a way that keeps me and the rest of the team happy.

Every day she continues to check in with me to make sure I remember when she is on and when she is off.


Give the employer a clear outline of simple tasks and grow in your role from there. You’ll have a much better chance of success.

3) You don’t establish lines of communication.

This is a huge one that I’ve never written about before. One of the unrecognized problems with free work is that it reduces the employer’s perceived ability to critique your work and demand more of you.

I know this from personal experience of taking free interns. You start to feel like, while their work is subpar, you can’t say much because they’re giving you such a good deal. I’ve started to do some small payment no matter what just so I have the “right” to ask for better work, but most employers won’t do this.

It’s your responsibility to open a line of communication with them. Make sure they know that you want feedback, you want to make sure the work you’re doing is valuable, and you won’t get offended if they critique it.

In other words, give them the permission to “yell” at you, and you’ll spare yourself a lot of headache down the road.

How to sidestep all of the above

Imagine if, instead of making a proposal to someone, you just did the job up front. You would avoid the lack of clarity that comes with most free work proposals. There would be no expectations from the employer because the task would already be complete. This would give the employer an opportunity to give a falsifiable (yes/no) answer to what you created.

Welcome to Free Work 2.0. Rather than asking for work, you’re delivering the work.

Here’s an email I got from an employee I hired recently (before she got the job).

In one short project, she avoided all the pitfalls of free work and landed herself a paid position. Sometimes it’s that easy.

After all, “free work” is what you make of it, just like anything else. I continue to advocate for it because, in terms of landing new opportunities, there’s nothing better.