• Praxis
  • A Complete Guide to Building Your Career Using Free Work

This post will show you how to get any job you want, with or without a degree. It outlines how I’ve been able to become a Director of Marketing at age 22, work with companies all over the country, and it gives you a practical framework to do the same.

The entire guide will be updated and revised in time. If you would like to receive updates or schedule a call, please email admissions@discoverpraxis.com.

A Complete Guide to Building Your Career Using Free Work

It wasn’t supposed to be this way.

I was NOT supposed to be the one giving them career advice. They were soon-to-be college graduates — I, a college dropout who was barred from the University of Michigan after achieving a 0.0 GPA two semesters in a row.

The roles should have been reversed.

And yet here they were, on the island of Rhodes after a talk at their conference, asking me how to get started on their careers.

One of them even asked if I was hiring an intern.

I couldn’t blame them. None of what I did to set myself apart during my early career days was being taught in colleges. In fact, I remember in college being actively discouraged from it. We’re taught to go to school, get good grades, take an internship, get letters of recommendation, attend recruiting fairs, apply to the most prestigious companies, and we’re all but guaranteed a great job with an amazing salary.

The truth is these activities are a distraction from the few things that actually matter.

As I listened to their concerns, it became clear to me that there was one thing, in particular, they could do above all else to overcome their lack of skill, experience, and network. It’s counterintuitive and it was downright offensive to some of them, but I knew it worked because I’d done it myself over and over again throughout my career to land opportunities that I was totally unqualified for on paper.

I told them to offer to work for free.

My Story: How I Used Free Work to Become Director of Marketing at a Startup

I’m going to tell you a little-known story about how I got my current job at Praxis.

It begins in January 2015. I’d been following Praxis for a good while since I dropped out of school. I loved the philosophy behind the program and thought (and still do) that Praxis was the only company that was challenging the higher education system in any serious way.

Though I loved taking online courses in subjects that I was interested in and think that they are one of the best ways to learn new things outside of school, it was hard to see them as revolutionary when it appeared they just repacked traditional learning into a digital format.

Praxis was something radically different. It flipped the conventional wisdom entirely on it’s head and said: “to heck with all this content consumption, start creating things NOW.”

I knew I had to work with them.

Here’s the problem, though: they weren’t hiring and I figured when they were, they wouldn’t advertise it. What’s more, though I had solid experience and was making great money working in eCommerce marketing, building eBay and Amazon stores, and doing contract work, I had never worked at a startup and Praxis had a product that might require something mostly beyond my current skill set.

I needed a way to get my foot in the door, and so I used the application form on the website to pitch them on a little arrangement. I would do photography and videography for them for free in exchange for the opportunity to work with them and the experience I knew it would bring.

They agreed and by February I was doing my first shoot for them. I did good work and used this first demonstration of my value to pitch some more ideas to our Founder Isaac. He accepted.

Pretty soon I’d become so valuable to them that they started paying me. One opportunity led to the next, my roles and responsibilities expanded, and I’m now running the entire marketing department at what I believe to be one of the coolest companies in the world today.

Free work…it works.

Interested in transitioning from student to entrepreneur? Download the Praxis program guide to learn more.

What’s the Deal with Free Work?

You’re probably thinking to yourself “great, it worked for you with one company that is already very nontraditional. So what.”

While it’s true Praxis has a different culture than many companies, free work was my go-to starting point for every major opportunity, big and small, I had during my first year or so getting started. I used it to get job offers and freelance contracts from companies ranging from commercial real estate to craft brewing.

It’s a simple, effective, and highly reproducible strategy for sidestepping the traditional barriers to entry in almost any industry.

Here are four reasons it works so well:

  1. It lowers risk and upfront cost for the employer. What many young people coming out of college today don’t realize is how expensive it is to hire someone and how difficult it can be to fire them. The reality I’ve learned as I’ve worked with more and more businesses as that business owner are terrified of making the decision because a slip up can often turn into a $10,000 mistake very easily. Recruiting expenses, onboarding costs, lost time, and employment benefits add up fast. Free work is a sort of testing period where you can let the employer see the kind of value you create for them and earn their trust. It’s very hard to do that when you’re asking for a paycheck and benefits right away.
  2. It lowers initial expectation and lets you learn on the job. If you’re a young person today, the unfortunate reality is that you’re probably not as prepared for the workplace as you think. Taking a normal starting salary raises the performance bar and an employer will be much less forgiving of the mistakes you’re bound to make when getting started. Free work gives you a buffer period where you can get used to working in a new environment, build your skills, and learn to be a valuable employee.
  3. It makes you more competitive. I remember after getting hired by one client getting to look at all the resumes of the people who had applied for the same position. There were hundreds of them. There’s no way I could have been competitive in a pool of people who are essentially identical in education and experience (none). Free work de-commodifies your application and lets you compete against people with far more skills.
  4. It makes it easier for you to walk away. What if you don’t like it? With a free work arrangement, you can walk away anytime you want without feeling guilty. The company has lost no money and you’ve burned little to no social capital.

It’s important to remember that the goal is not to work for free for a long time. It’s to get your foot in the door so that you have the opportunity to transition to paid work as quickly as possible.
Before I share how to get started, we need to break down a few myths about free work.

Questions and Concerns (or, Isn’t this Exploitation?)

Let’s set the record straight about free work once and for all. Here are some of the common questions I get when I speak to young people about this:

1. Isn’t free work, like, exploitation?
Free work is a temporary, voluntary relationship between an employer and a young person. The employer provides experience and the chance to prove oneself while the young person provides some small value for the employer. Consider it like a free software trial. Both parties get to test out the relationship in a risk-free environment. That’s the opposite of exploitation.

If however, you reach a point where you’re creating a ton of value and the employer refuses to pay you, perhaps it’s time to move on. The good thing is you’ll have a portfolio of skills and experiences that you can take to other companies now.

2. Aren’t I just going to be making money for everyone else but myself?
Hold on. You don’t even know that you’re capable of doing that yet. In order for an employer to pay you, you have to be able to make more money for him and his business than you take out of in salary and benefits. That’s hard! Chances are you’re not going to be able to do this for at least a couple of months. The money will come, but it has to be created by you.

3. How long should I work for free?
I like to have very clear parameters around my arrangement. I pick 1-3 projects to deliver on for free and I ask to start getting paid once I’ve finished. Setting clear expectations is important. How long will this take? I’ve seen people transition into full-time work in 1 week and I’ve seen it take up to 6 months. It depends on the needs of the company, the speed at which you learn and work, and the projects you’ve picked. I would budget for about a month, working at a pace of a few days a week.

Getting Your First Job 101: How to Make an Effective Free Work Proposal

Bestselling author Ryan Holiday recently wrote an article titled “Sorry, Offering to Work for Free is a Really Bad Strategy.”

I agree with him. Most young people who try their first free work proposal blow the opportunity badly. I get messages all the time that go something like this:

“Dude. I love what you do. How can I get involved? My skill set is pretty diverse and I’m willing to work for free. I just want to be able to prove myself.”

I usually ignore messages like this, not because I don’t appreciate the request, but because I don’t like being put in the position of having to tell people “no” and I honestly usually have no clue what I have that needs to be done.

Messages like this are a distraction and ultimately do me, or whomever you want to work for, a bit of a disservice. It asks a favor of them while proving no clear reason they should be giving one. Before you send in a free work proposal, you need to do some serious thinking and ask yourself a few questions:

  1. What is this company currently doing (or not doing) that I can help them do?
  2. How can I help them do it?
  3. Why is this valuable to them?

In other words, you need to have a value proposition for the employer. Your value proposition is how you stand out in the job process and ultimately prove that you’re not another college graduate who thinks they deserve a job because they have a degree. It’s the difference between the entrepreneur mindset and the student mindset.

To illustrate what I mean, contrast the above message with this one that Charlie Hoehn used to get hired by 4-Hour Work Week author Tim Ferriss.

Mr. Ferriss–

After visiting your site countless times since May ’07, I’ve come up with a few suggestions that could improve your readers’ experience. Here are two of the things I think you need…

1) A network of your followers: Right now, you have a lot of passionate and devoted readers who comment on your blog. These are people who are likely to spread your ideas. You need a place where your loyal readers can interact with each other more freely, and share their stories about how your book has inspired them.

What it would take: A micro-network. You could frame it as “a crusade against the 9-5 workday.”

How I could help: While I was interning for Seth Godin, I learned how to create micro-social networks for very specific niches. I could easily set this up for you, making it a more exclusive “invite-only,” if you wish.

What the benefits are to you: Allowing your most devoted readers to share their lifestyle design stories will provide you with even more case studies for blog posts (or for a follow-up book). It will also serve as a spot for your readers to get to know one another, and they’ll appreciate that you’ve given them that opportunity.

2) A more dynamic “About” page: Currently, this page starts off with a quote about you from Albert Pope, followed by three thumbnail pictures of your face and a great deal of text outlining your achievements. While your credentials are impressive, this page doesn’t really capture your personality or the lifestyle you’ve designed for yourself.

What it would take: You need a video, between 2 and 5 minutes, that captures the excitement that comes with lifestyle design. The video would showcase exciting things you’ve done (skydiving, tango, motorcycling, etc.), and would be a great way to show your readers that you are the real deal.

How I could help: I can make this video for you for free. I’ve been editing video for more than four years and started a business in creating movies for special events. All I would need to make your video are great pictures and videos of you. The more they show the human side of you, the better.

What the benefits are to you: Reading something is fine, but an image is far more powerful. This video will establish an even deeper credibility with your new (and old) readers. Even if you end up deciding that it’s not right for your site, you’ll still be getting a great video about you that would normally cost several hundred dollars. If you like my work, we can discuss other ways to implement videos into your site (including higher quality and more exciting videos for your blog).

In exchange for these things, I hope that you’d consider taking me on as an intern (real-world or virtual). I would love to help you out on future projects. Let me know what you think, and I look forward to hearing from you.

Charlie Hoehn


This is just about the most effective value proposition I’ve ever seen. It’s brief, it’s bright, and it has a couple solid deliverables that Charlie clearly spend a good deal of time thinking about in advance. More importantly, the projects are simple, low risk, and can be done with little cost to Tim.

How could he turn it down?

Whenever you’re proposing to work for a new employer, free or not, you should do as much as possible to think in terms of what is valuable to them. Rather than asking for a favor, you’ll be trading value for value. Rather than asking for a job, you’ll be creating a job.

How to Choose Companies for Free Work Opportunities

Not all work opportunities are equal. While I’m generally an advocate of taking whatever you can get, putting a little bit of thought and planning behind how you choose companies to work for can help you dramatically accelerate your professional growth.

If you’re a high performing individual, chances are you’ve been told the best opportunities exist at big, prestigious companies. Certainly, there’s a lot you can get out of that, but there are tons of unsung benefits to working at lesser known small businesses, startups, and on freelance projects. Things off the beaten path also tend to be more receptive to alternative work proposals because there is less bureaucracy.

That means you should be looking for opportunities through friends, from local businesses, from family, or from startups from whom you buy products or services.

The questions I normally ask myself once I’ve found a company I might be interested in are as follows:

  1. Does this opportunity afford me the chance to develop hard skills and experiences that I don’t currently possess?
  2. Will I get the chance to work directly with the founder, CEO, or another experienced professional?
  3. Will be afforded a big picture view of the entire company or project?
  4. Is the workplace highly bureaucratized or does it encourage internal entrepreneurship among its employees?
  5. What are some easy ways I can create value on day one?

In terms of priority, question #2 is by far the most important. On multiple occasions throughout my childhood and my career I’ve had the chance work directly with the founders of companies. My relationship with the CEO of Praxis has led me to learning more than I ever could have learned in a more compartmental role, speaking opportunities, clients, friends, travel, and more. I believe in its ability to accelerate your career so much that we’ve built this into the Praxis experience, but regardless of whether you do Praxis or not, you should be heavily biased towards it.

Case Study: How Reese and Reagan Found a Company to Work for Through Reddit

Reese and Reagan Brookes are twin brothers in college whom I met whilst doing photography at a FEE seminar last summer.

After following my blog for a while and the posts we write here at Praxis, they’d decided enough was enough. They wanted something more than school and didn’t want to wait until they got their degree to start working.
They had a problem, though. They had no idea where to look for work opportunities. One day they came across a Reddit user who had founded a startup that was operating in Beijing and Vietnam.

In their words:

“We exchanged a few brief messages back and forth introducing ourselves and said we’d be willing to work for free. Next, we spent a couple of hours working on a 7-page document showing 5 specific ways they could improve their website to increase sales and land more partnerships with other companies. He was extremely impressed. He didn’t ask if we had any prior experience. He didn’t ask for a resume or an official interview, and within just three hours of meeting him, we were offered a job! Starting next week, we will be working with the company on their content creation and digital marketing for China and Vietnam.”

The myth that companies aren’t hiring is wrong. A simple search through your Facebook feed (or Reddit) is often enough to find one that you can develop a free work proposal for. Resolve now to start looking in unexpected places for unexpected ways to create value.

Opportunities are there for your taking.

Moving Forward: What to Do Next

If you’ve finished this post, you’ve now got a solid operating framework to use for landing your first opportunities. In other words, you now have no excuse not to get started.

I’d like to make an offer to each of you. If you a) identify a company to work for and b) create a free work proposal, someone at Praxis will review your document through 30-minute coaching session that is normally reserved only for participants.

Just shoot an email to admissions@discoverpraxis.com and we’ll get you set up.

And if you’re interested in getting a fully immersive apprenticeship experience, consider applying to Praxis or scheduling a call.

Your future awaits.