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The Ultimate Guide to Apprenticeships

Note: This is a big article! Click here to download a beautiful PDF you can read it later at your leisure (and also get free updates on apprenticeship opportunities from around the web.)

Over the last decade, the internet has increased the flexibility in where and when we work. Remote work has become increasingly common across many different industries. Companies appreciate the cost savings of not having to have an office and the ability to hire globally instead of just locally, and individuals appreciate the increased flexibility and potential number of employers.

The internet has also changed how we work. A “traditional” career path was to go to school, learn a skill and practice that skill for the rest of your life. The “new” career path is marked by constant learning and evolution.

A key part of this new career path is the idea of apprenticeships. For career starters or someone looking to make a career change, an apprenticeship is a way to make that transition — not unlike graduate school over the past few decades.

The premise is pretty straight forward: you find someone that is doing what you would like to be doing in five to ten years and cut them a deal. “I’ll come work for you and I’ll create results in your business. In exchange, I want to see the inside of how your business works: how you launch products, what the industry looks like, and who I need to know.”

Apprenticing was how I started my career. I taught myself a bit of Search Engine Optimization using Moz’s Beginner’s Guide to SEO, a free guide online. I paid $20 to get a hosting account from and built a website outside my job at the time. I cold-emailed a handful of marketing agencies and used those sites as proof of my skills. That turned into a full-time job where I learned a lot about internet marketing, project management, and technology.

Other high profile examples of apprenticeships are Charlie Hoehn, who originally worked with business coach Ramit Sethi and then author Tim Ferriss as an apprentice for a few years.

New York Times bestselling author Ryan Holiday apprenticed for author Robert Greene, author of five international bestsellers including The 48 Laws of Power and Seduction, before launching his own best selling book, Trust Me, I’m Lying.

We will walk through what exactly an apprenticeship is, your options for getting one, why you might want to do it, as well as extensive step-by-step instructions to help you land an apprenticeship.

What Is An Apprenticeship?

For many, an apprenticeship conjures images of laboring as a beginner mechanic or tradesman. An ongoing tradition begun by medieval tradesmen like carpenters or blacksmiths passing on skills to a young journeyman in their guild.

Apprenticeships, in the sense we are talking about them here, are similar in that they emphasize hands-on practical experience over theoretical understanding.

It can be helpful for a blacksmith to read in a book about how to make a horseshoe, but all the book studying in the world won’t replace hands-on experience working with metal.

In the same way, many careers today benefit from a theoretical understanding of the material that can be gleaned from studying, it is no substitute for hands-on work.

In large part, this is because industries are changing so much faster now. I had a friend that was hired to help revamp a course in social media marketing as part of a graduate program, but quit when he realized that teaching this type of material in a graduate program was hopeless.

The curriculum was changed every five or ten years and the updates to the curriculum could take years to happen. The platforms that the professor was talking about like Twitter or Facebook change every month if not every week.

By the time the marketing techniques were taught in the classroom, they were hopelessly out of date. The students were left with much lighter pocket books but without the skills they needed to land a good job.

This same phenomenon is happening to other roles like software development, design, and marketing. All the best developers, designers and marketers I know didn’t learn in a traditional educational system, they learned on the job.

As more and more of the economy becomes subject to this logic, and the roles in our organizations become more nuanced and less reliant on knowledge alone, apprenticeships are slowly re-emerging to fill the gap in the university education system.

As we’ll explore in this guide, apprenticeships are by far the best way to help you learn new skills, build an amazing career, find work that you truly care about, and get an entry-level remote job.

Why Should I Get an Apprenticeship?

First, apprenticeships are paid. Unlike going to college or graduate school where you are paying to learn, an apprenticeship means you get paid to learn. Not only will you be learning skills that will set you up to work remotely for as long as you like, but also you will be paid.

Second of all, apprenticeships are an opportunity to develop relationships. You will be in close proximity with a professional experienced in whatever area it is that you wish to acquire skills. Instead of learning from someone who was working in the field a decade ago, you are learning from someone who knows the most up to date information about what is happening in the field and building relationships with them.

Third, and most importantly, an apprenticeship is about learning how to learn.

In my book, The End Of Jobs, I talked about why developing an entrepreneurial mindset is an incredibly important component not only for building a great career in general, but also for flourishing in the increasingly complex, fast-changing reality of the modern economy.

An apprenticeship is a way to work in the weeds and develop a more entrepreneurial approach to your career which will open up more opportunities in the long run.

To be sure, apprenticeships are not for everyone. If you want to be a doctor, lawyer or physics researcher, there are academic requirement for those.

But for many people, apprenticeships are the best option for working directly with an experienced professional who will help you learn the skills you need to be successful in the modern economy.

To Remote Or Not to Remote? The Benefits and Realities of Remote Work

Before we get into the nitty gritty of how to get an apprenticeship, it’s worth slowing down to consider what exactly it should look like. Because there are not a huge number of companies offering apprenticeship type roles, it can be easier to find roles remotely rather than just looking in the city you live in.

Remote apprenticeships have some other benefits and challenges.

One benefit is pretty clear: you can work from wherever you want, and often set your own hours. This increases the amount of flexibility you have in your life.

However, the inherent benefits of remote work are balanced out by responsibilities.

You will need be more independent. Without having a manager or supervisor glancing over your shoulder in the office, you will need to be more accountable for delivering results, and more resourceful in getting things done for yourself without a team always around you.

A remote apprenticeship is still an apprenticeship, and the companies you are working with will demand a high level of integrity and reliability. You also will have to take responsibility for your own learning and development. That means asking for feedback and reading and studying on your own time.

You will need to be more disciplined. Not only will you need to be more independent, resourceful, and accountable, but you will also need to provide the structure to your day-to-day life. This is a lot harder for some people than others, and a lot harder for pretty much everyone than they initially think.

You will need to master blocking out working hours, developing a solid morning routine, and planning your social life better.

The main advantage of an in-person apprenticeship is the higher bandwidth relationship you’re able to develop with your manager and colleagues. In the same way a journeyman blacksmith picked up a lot just by watching the master work, being in the same physical location can increase the speed at which you learn.

How Apprenticeships Work

An Overview

Remote apprenticeships started primarily in the technology industry as it started with software development. It has extended to many roles including:

  • Software development and engineering
  • Design
  • Marketing
  • Inside Sales
  • Customer Support
  • Accounting and Bookkeeping
  • HR

From this list, it should be clear that if you want any kind of remote job, you’re going to need some relatively technical skills.

The keyword here is relatively. You won’t necessarily need to put your head down for two years to learn how to code, but you will still need to read some books and undertake some self-guided education in order to figure out just what you need to know to break into what may be a completely foreign industry.

The best way to walk through what a typical apprenticeship looks like is to look at the first 6–12 months of an apprentices journey.

0–6 months.
To get an apprenticeship, you’ll either apply for a role where the employer explicitly states they are searching for an apprentice, or you’ll join a small company or startup in an entry-level role where you’ll have to perform multiple roles.

In either case, you will be in the weeds, often wearing a lot of different hats.

A typical apprentice may start with something like customer support or managing some existing operations that keep the business running. After some time, you might move on to executing some core processes for the business: talking to customers, publishing marketing materials, managing communities, or other more central roles.

These tasks will often come with an increase in the amount of responsibility you are handling, and also will be the first stepping stones towards gaining competence and building some real skills.

6–12 months
After a few months, the expectation will shift slightly. From the beginning, there will be an implicit expectation that, as an apprentice, you will eventually grow your skills to the point where you will not just be operating the existing business but creating new processes and initiatives.

What this looks like depends on what type of business or industry you are working in. It could be as diverse as coming up with strategic recommendations from data analysis, putting together proposals for new products, optimizing a sales funnel — anything that actively helps build the business and increases the bottom line.

12–24 months.
The turning point in the apprenticeship usually comes between one to two years in. That’s the point where you’ll start to take charge and not just create new processes and initiatives, but then put them into action.

You’ll start to act as an “intrapreneur,” driving forward the business.

Most apprenticeships tend to last for 2–4 years. That’s a time frame over which an apprentice can build the skills they need to succeed and still contribute back to the business.

At the end of an apprenticeship, you will have a track record of creating real results, an extensive practical skill set that you obtained while doing so, as well as relationships within the industry who will now know you as someone who gets things done.

This is a position of strength from which you can elect to stay with the existing company but in a more senior capacity, move to another company, or start your own.

How to Get an Apprenticeship

There is usually a clear path that people who successfully land apprenticeship positions follow:

Step One: Choosing a skill to start learning — one that aligns with their interests and will eventually be useful in an online business.

Step Two: Demonstrate you are a self starter and organized — by showing that you are willing to teach yourself that skill through building a side project.

Step Three: Apply for an apprenticeship — trying to work with a company that will help take them to the next level.

This seems simple — and it is. We’ll break down these three steps so that you will know precisely what to do in order to get an apprenticeship with a great company.

By following this path, you’ll exhibit the traits employers look for in an apprentice:

Self-starter: Everyone that has a degree from school has proved they are able to follow directions when someone tells them what to do.

Because you built a side project without anyone telling you to, you’ll show that you’re the kind of person who doesn’t just follow direction, you take the initiative. You will show that even though you don’t have a strong skill specialisation that would traditionally be valuable to a company, you are the type of employee who will be self sufficient and take responsibility for getting things done.

Organized: In order to launch this project, you’re going to have to get yourself organized. It doesn’t matter what system you use; it matters that you can have projects and tasks handed off to you and that the person handing them off knows they won’t fall off your plate or get lost. (I would recommend that you read and implement David Allen’s Getting Things Done. It will pay dividends for the rest of your career.)

Note: This is a big article! Click here to download a beautiful PDF you can read it later at your leisure (and also get free updates on apprenticeship opportunities from around the web.)

Step One: Choose a Skill To Learn

The first step is to figure out one skill you’d be interested in developing. There are a lot of potential options.

Are you a competent writer? Learning more about psychology and sales letters can lead to copywriting, which is useful in any business.

Do you have a decent artistic sense? Learning about graphic design might be a good option.

To help you out, here’s a list of business skills which all have two things in common:

  • They are free or cheap to learn. Reaching a basic level of competence in any of them will cost you about as much as taking a class at a community college (a few hundred bucks).
  • They are all extremely valuable. While it may cost very little to start learning the basics of copywriting or SEO, those who become good at them can make very good incomes.

You won’t have to become an expert at these skills, but you will have to be genuinely interested in learning them.

Your side project acts as a portfolio demonstrating you are an organized, self-starter with some core competency.

This list is by no means exhaustive, but contains the most common skills I’ve seen apprentices develop.

Here’s a few of the most common skills that apprentices develop with a side project:


Written Content / Copywriting

Copywriting is a great starting point for anyone looking to write online, as it serves as a foundation for any other skills you might want to learn.

Write great copy, and you’ll find yourself getting better click-through rates in your emails, ads, and landing pages.

The biggest benefit of learning copywriting is learning about sales psychology and positioning.

Here are some of the classic books in the field that are worth studying.

Offer your services on a site like Upwork to get practice writing and start to develop a portfolio.

Media Content: Video and Audio Production

Lots of businesses are increasingly using platforms like Youtube (video) and podcasting (audio) to reach their customers.

Knowing how to create engaging videos is an increasingly powerful and viable way of providing value to a business, and it’s a skill many employers are on the lookout for.

Watching YouTube tutorials for your chosen software setup is a great way to get started.

Then set up your own Youtube channel or podcast on a topic that you’re interested in. After a few months, you’ll have a concrete projet to show a potential employer.

Email Marketing

Learning how to build an audience through email and providing ongoing, valuable communication is the backbone of almost every online business.

Email is your most direct line to the people who care most about your products or services.

Having a basic understanding of list building, open rates, list churn, and click-through rates is a great way to show employers that you’re serious about helping to build a platform. Here’s a nice intro.

Search Engine Optimization (SEO)

Millions of people make Google searches every day. Search engine optimization means knowing how to get a page to show up one of the top positions for a particular search term.

This is one of the most effective online marketing channels with companies spending over $65 billion per year to improve their sites visibility.

Check out MOZ’s beginner’s guide for a great walkthrough and set up your own site using their prescription.

Social Media

Community Management

Community management is about being able to consistently engage members and grow the size of a group, forum, or other platform. Great community managers help increase a brand’s trust, attention, and loyalty over the long term across social media accounts.

While audience building is concerned with numbers, community management is based on culture and longevity.

Many businesses invest a lot of time in maintaining strong communities. With the potential for increased lifetime value of customers, as well as long-term strategic competition on the table, hiring someone who understands communities is a sensible option in many cases.

Buzzing Communities by Richard Millington is a great book on the subject to start learning.

Use the tools in there to set up a community based on a subject you’re interested in. This could be gardening, fashion, or watches.


Design and User Experience

Without good visual communication on a website or app, even the best ideas can fall flat. Designers make it easier to ensure web content is usable and gets to the point.

User experience (UX) takes it a step further and applies design principles to make sure desired user action is taken in the right places.

By learning about good web and UX design principles, you’ll be able to increase conversions and sales across an entire business if you really know what you’re doing.

Read a book like Design for Hackers and design your own homepage.


Front-End Development — HTML, CSS, and Javascript.

Having a rudimentary understanding of some HTML and CSS should be considered almost essential for working online. You don’t have to know how to code masterpieces, but learning a few tags and what they do is the difference between competence and floundering.

Basic HTML will naturally come just by being exposed to it, but for those who really want to take it to the next level, learning a markup language like CSS or Java can give you some serious creative power, especially combined with some design sense.

Coming into a business armed with the ability to turn CSS upside down and make easy changes to web content is supremely valuable to anyone you work with. This is one small area of technical skill that can make a difference in how successful you are online.

There are many free online courses which teach HTML, CSS, or Javascript.

Back-End Development — Ruby, PHP, Python, and Others

Learning one of these back-end languages will give you an extremely sought-after skill set that is always in demand by startups and online businesses.

On the internet, they say “coding is the new literacy.” If you can get on board with that, you’ll be able to help improve a business’s products, marketing, and processes in a massive way.

There are many free online courses which teach Ruby on Rails, Python, or PHP.

Step Two: Start a Side Project

After choosing a skill set that interests you, it’s time to start practicing those skills by getting started on a side project.

This will demonstrate to employers that you are a self starter and organized — just the type of person they would like to bring into their organisation.

What exactly is a side project? A side project can be anything from managing a monthly newsletter to building a full e-commerce site.

A good side project:

  • Lets you dip your feet into the online business world and see if it’s for you.
  • Provides you with a testing ground to try out whatever skills you are interested in learning.
  • Gives you an online resume (CV) that shows what you’re capable of, that you are self-directed, and that you’re able to work on your own.

While you want your business idea to be viable, the point of a side project isn’t to get rich. Its purpose is to give you a platform to test out new skills, learn as you go, and have a project you can show to employers.

It doesn’t matter how successful it is, but rather how much you learn while you do it, and to what degree it successfully demonstrates that learning.

The real beauty of a side project is that you can learn anything you wish.

If you’re interested in learning about HTML and CSS, you might tinker with the User Experience (UX) of a site and see actual changes in the appearance of the page, as well as how it affects your revenue.

Like making videos? Make it part of your side project to show your skills.

Whatever skills you are interested in, you can experiment and learn by using them in real life, instead of just reading about them. Your side project becomes a living case study of your entrepreneurial ambitions.

Choosing a Side Project

One of my first side projects was a small site built for college students looking to buy cheap, used furniture to fill their dorms (the now-defunct In order to set up the site, I had to learn the basics of HTML and CSS. In order to get it to rank in Google I had to learn some SEO and copywriting.

As far as side projects go, this hit all the marks:

  • I got real experience running a small business that solved a real-world problem.
  • I had a testing ground to learn real skills.
  • I was able to directly serve the needs of an existing market, as well as teach myself SEO as I went.
  • I eventually used the site to get an apprenticeship with an SEO agency.

While I wasn’t laboring over creating an entire skillset from scratch, working on this small site gave my future employer evidence that I was willing to learn, a self starter, and organized.

Here are some other side projects which I’ve seen people do to prove their skills:

Side Projects: Where To Next?

Let’s say you’ve decided to start a Side Project in the form of a WordPress blog reviewing Air Fryers. You write a new blog post each week filled with affiliate links, since this is a great beginner revenue model that matches well with niche review sites.

It may then enter your mind (after putting together a simple marketing plan) that you could do with learning some SEO to leverage free traffic to your site from Google.

After tinkering with SEO, and with users now coming to your site, you might then decide to build an email list using free tools. From there, you could set up autoresponders and redirect traffic back to your affiliate links perennially.

Before you know it, you have learned how to do email marketing, SEO, and make a website. You have the evidence to show an employer.

At this point, some people find that they would rather just keep working on their side projects and see if they can grow it into a full time gig.

The idea behind an apprenticeship is that instead of going it alone, you can leverage that side project to learn from a more experienced manager than can accelerate how fast you are acquiring skills.

By helping a mentor build their business, you’ll often fast-track your earning potential to a level far beyond what would typically be achievable on your own in the same time frame.

A former apprentice, Cory, described his decision to give up his side project and go all in with an apprenticeship this way:

“By no means would I have the ability to make the impact that I can, work with the types of people I am, or work with the resources I have. The experience would be much more hollow.”

Step Three: Leverage Your Side Project to Get an Apprenticeship

So how do you actually leverage all of this work and learning to find a company that is willing to take you on?

If you’ve followed the advice above, then by this point you are an ideal apprentice candidate.

Now it’s only a matter of finding a business you’d want to work with, and figuring out ways to help them out and get involved in what they are doing.

Four Proven Strategies for Finding an Apprenticeship

1. Look for Local Companies and Networking Groups

One way to find an apprenticeship is to look around for companies in your local area that are hiring.

I got my first apprenticeship by taking the site I’d built and sending it around to local marketing agencies in Memphis, Tennessee.

I Googled “Marketing agency Memphis” and emailed everyone that showed up on the first two pages of Google. I explained to them that I had been teaching myself SEO and sent them a screenshot of some of the keywords I ranked for.

I asked if they were hiring and explained that I wanted to learn more and was willing to work for cheap to get started.

A few replied, and I ended up getting 20 hours of part-time work from one. That eventually turned into a full-time position as a project manager.

2. Cold Email the Inc. 5000 List

Another option would be to cold email companies you’re interested in working for outside of where you live. If you’re willing to relocate or they offer remote positions, this can be a great option.

I know a few people who have gotten apprenticeship-like roles by emailing companies on the Inc. 5000’s fastest-growing companies list (like Empire Flippers).

Being on the Inc. 5000 list means they are growing fast, which is good for two reasons:

  • They need to hire a lot of people.
  • You’ll get to move up the organization quickly.

Fast-growing companies require their team members to grow fast, too, which is exactly what you want in an apprenticeship.

This will also force you to get good at cold email. Noah Kagan of OkDork has written multiple times about best practices for cold emails. Here’s another one.

3. Follow Companies You Would Like to Work For

If there is a specific type of company you want to work for, follow them on email, Twitter, LinkedIn, and Facebook, and see when they are offering new positions. Whatever they post will give you an idea of what kinds of skills you’ll need to develop in order to provide value to them.

By identifying a direction you want to go in, you can use the side project to teach yourself those skills. Then it’s just a matter of cold emailing, and finding what you can do to start helping out.

4. Sign up for

For the past couple years, I’ve been running a site that helps connect apprentices with small businesses and startups for marketing, sales and operations roles.

We’ve placed dozens apprentices within exciting companies where they’ve learned, grown and built the foundation for a strong career.

We send out a curated newsletter every Monday with the best new apprenticeship positions from around the web.

If you’re going after your first non-technical apprentice job at a startup​, you can sign up for free to hear about new positions.

We also work one-on-one with select companies to handpick the most talent apprentices from those who subscribe to our weekly updates. If you’re interested in hiring an apprentice, you can learn more here.

Action Steps:

Today, apprenticeships still seem novel. In fifty years, I think we will look at apprenticeships in much the same way as we look at an undergraduate degree today. It will be a default part of a “smart” career path.

Apprenticeships create a win-win opportunity for individuals in a fast-changing career environment and companies around the world. Apprentices get paid to learn valuable skills that will serve them over the long-term, while giving employers a way to recruit talented, motivated team members.

By following the three steps we just went through, you’ll be well on your way to obtaining an apprenticeship with a great company.

To recap, the three steps to finding an apprenticeship and your first entry-level remote job are:

  • Choose a skill to learn. Pick an online skill that you are drawn to, have experience in, or think you will be good at. Start teaching yourself as much as you can about it.
  • Start a side project. Whether it’s pursuing an interest or setting up a business, build a side project where you can apply, learn, and grow your skills.
  • Leverage your side project to get an apprenticeship. Use your side project to show off your skills and show how you can provide value. Do this to start working with a business you want to be part of and learn from.

To get started:

  1. Sign up for free at Get Apprenticeship. We’ll send you 3–5 new apprenticeships at great companies to your inbox every single Monday. You’ll start to see what kinds of skills real companies are paying for that you could dvelop.
  2. Start thinking about your side project. Write down 5–10 ideas of hobbies you’re into, interests you have, or ideas you’d like to explore. Do some research to see if there are existing communities for these already on the web. Maybe you’re already part of some of these communities — how can you add value to these communities? How can you be of service to people similar to yourself? What can you provide that people will pay for? These are the sorts of questions you should be asking yourself to get into the entrepreneurial mindset.
  3. Subscribe to updates from companies you love. While Get Apprenticeship will send you updates from companies we love, you should personally subscribe to updates in whatever way you can from the companies you would love to work for.

The Ultimate Guide to Apprenticeships was originally published in The Mission on Medium, where people are continuing the conversation by highlighting and responding to this story.

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