When I was a college freshman, I was pretty sure I had the next 8-12 years of my life mapped out. Sure, there were little details I was unsure of, like how I would pay off the money borrowed to afford four years of private college, or where I would live after I graduated, but overall I thought my path was pretty clear:

4 years of undergrad, then another 4-8 years getting a PhD (with a 2-year stepping stone of getting my Master’s). Final career: academia, probably a professor of English at a college not unlike the one I currently attended.

Four years later, and my life (and goals) would be unrecognizable to my 18-year-old self. I’ve now scrapped all ideas of pursuing any further formal education, and I’m doing work my younger self didn’t even know existed (and that, 20 years ago, didn’t exist, period).1

But that doesn’t mean I plan to stop learning. Quite the contrary: now that college is over, I plan to learn more in the next year (and many to follow) than I did in my four years of undergrad. In essence, I’m creating my own Master’s degree. What follows is an account of how (and why) I plan to do it (and how you can do the same).

We’ll start with why.

Avoiding Stagnation

After “formal” education is over, it’s all too easy to stop learning. You settle into a career, collect your paycheck, put on a few pounds, maybe take up wine collecting, and before you know it twenty years have gone by and your head isn’t any fuller than when you left college (maybe even a bit emptier).

This is an extreme example, one that assumes you never have to learn anything new as part of your job and never travel, move to a new place, make new friends, or even take an online course. It’s also highly unrealistic in light of today’s job landscape–the days of spending ten years (let alone a lifetime) at the same company are over for most people.

Still, the danger of stagnation is very real. Specifically, stagnation is detrimental in two ways:

I. Professional Obsolescence

You may stop learning, but the world doesn’t stop changing. The pace of change is faster than ever, with new jobs being invented even as emerging technologies threaten to render historically “safe” careers such as accounting or truck driving irrelevant.

Furthermore, even in fields that are (for the moment) safe from automation/outsourcing, there’s still danger of falling behind and becoming irrelevant. If you’re not constantly learning and progressing, the people in your field who are will eventually overtake you. At best, you’ll lock yourself out of advancing much beyond your current position or increasing your salary.2

Certainly, as a freelance writer it’s crucial for me to increase my skills and learn as much as I can. Freelancing is competitive, and can be a quick race to the bottom. Just check out the people on Fiverr charging $20 to write 500 words. Plus, automation is coming to writing, like it or not.

A computer can’t yet write an article like this one (current AI-written articles lack flair, to say the least). And there are valid arguments that it will never be able to craft coherent, long-form narratives the way people can. But for many of the writing jobs out there, that doesn’t matter.

Even writing that’s 80% as good at a fraction of the price (with no typos or grammar errors, working 24/7/365), will be a compelling reason enough to offload a good chunk of human writing work to computers. I plan to explore automation of writing jobs more in a future article, so I won’t get much more into it here.

Consequently, my current strategy is to stay as far ahead of the automation curve as I can, while also branching into other business opportunities and skill sets (more on that below). The mediocre writers will be the first to go, so I’m striving to be the best I can.

Frankly, that’s part of why I’m writing on this site–to give myself added practice and room to experiment with techniques without having to worry about a client’s expectations. I’m also continuing to do everything I can to position myself as an expert, even as I research the various writing opportunities I can pursue.

Regardless of your field, I encourage you to do the same. Whatever you do, don’t assume that your job is “safe.” Don’t assume you’re irreplaceable. Don’t underestimate the advance of technology or overestimate the goodwill of your boss. And sure as hell don’t overestimate your intelligence and knowledge. ALWAYS BE LEARNING!

II. Combating Atrophy, Evading Ennui

atrophy: Gradually decline in effectiveness or vigour due to underuse or neglect. – Oxford Dictionaries

ennui: A feeling of listlessness and dissatisfaction arising from a lack of occupation or excitement. – Oxford Dictionaries

In addition to the professional benefits of continuing my education, there’s another, deeper reason I’m setting myself on this path: to avoid atrophy and ennui.

Let’s start with atrophy. In a sense, this concern goes along with continued professional development. I don’t want my intellectual muscles to get weak from lack of use. I don’t want the same repetitive work to grind away at the keenness of my mind.

I think that being self-employed insulates me somewhat from this danger, since I only get paid for the work I do, not just for showing up. But the danger is still there, and I’ve even seen it happen with some of my client work. The pattern is that when I get a few clients and the money is good, I slack off in my efforts to find other clients, expand my work with existing clients, and expand my skills.

Furthermore, there’s also the temptation to create work that’s “good enough” or to follow the same formulas/formats that have worked in the past. In this sense, I’m just spinning my wheels, stagnating at best but more likely regressing.

As someone striving to become an expert writer, this kind of stagnation is unacceptable. So I have to keep finding ways to push my writing skills (more on how I plan to do this below).

Beyond even the goal of cultivating mastery, however, there’s another reason I mustn’t stop learning: ennui.

I first came across this word in an Irish literature lecture while studying abroad at Queen’s University Belfast (we were reading Maria Edgeworth’s novel of the same name).

It’s one of those words that captures a feeling that can be very hard to describe. If you’ve felt it, then you know. It’s not quite depression (though the two can go together). It’s much more the feeling of, as the definition points to, being “unoccupied.” And in my experience, that usually means a lack of intellectual challenge.

So how do we create intellectual challenge? Simple enough: spend more time learning and working to solve difficult and interesting problems.

Which brings us to the next section.

Building a T-Shaped Skill Set

It’s all well and good to say, “I’m going to keep learning and challenge myself intellectually.” But without concrete objectives, that’s just cheap talk. So where to start?

For me to spend time learning about something, it has to be, first and foremost, interesting. Bonus points, of course, if it’s also professionally useful.3 Below, I’ve put together a list of skills that meet at least one of the above criteria (most of them meet both).

Developing these skills (in tandem with more general reading about subjects that interest me) will put me on the path to becoming a T-Shaped person. You can read more about the concept of being “T-Shaped” in this blog post from Buffer, but the basic idea is that you go really deep on one skill (in my case, writing) while developing basic competency in a broad range of skills. The end result, then, is a skill set that looks rougly like a “T” when you represent it graphically.

graphical representation of my skills

A graphical representation of some of my content marketing skill set.

Here are my general skills and learning goals:

Learn Spanish to at least C1 level

I haven’t taken any formal exams, but I estimate my current level to be B1/B2 (skewing more toward B2 in conversation). To push my improvement, I’m working more reading into my daily practice and using Beeminder to make sure I practice every day.

Learn French to at least B1 level

I want to strategically learn it in a way that doesn’t interfere with my Spanish progress. I think my Spanish level is high enough now that starting basic French won’t pose a problem.

My reasons for learning French are many, but my primary interest comes from a desire to travel in both Québec and (Francophone) Belgium. I’ll start this learning project when I’m back from Colombia, and I’ll be documenting it on this blog.

Learn JavaScript web development

After reading Levels.io’s post on building a startup in public, I decided that my lack of web development ability is holding me back.

I don’t aim to have a career as a developer (at the moment), but having basic development skills will allow me to prototype and test business ideas that would otherwise require a partner or contractor.

Plus, it’s a compelling learning challenge. My current learning resources for this project include How to Learn JavaScript ProperlyA Study Plan to Cure JavaScript Fatigue, and Beginning JavaScript.

Transition from content writer to content marketer

This is as much a career goal as a learning goal, but it fits into diversifying my skills. My current freelance work focuses on writing articles for client blogs. There’s nothing wrong with this, but I’m finding it to be limiting in terms of the kind of freelance work I can take on.

So the next step, as I see it, is to learn about content marketing. This field includes writing, but it also touches on strategy, SEO, and other forms of promotion. In plain language, it means using articles, videos, infographics, and other media to attract and educate potential customers about a product or service.

I’m using Buffer’s guideNat Eliason’s guide, and books such as Traction to help me teach myself about this topic. Even more importantly, I’m using this site as a way to experiment with content marketing techniques.

Course and product creation

This is a more general goal, but as I mentioned above, I’m aiming to transition away from only freelancing. I want to diversify my income and add business activities that are, ultimately, more passive.

I’m in no hurry to do this, as I want to create a business that helps people (i.e., no drop shipping stores or domain name flipping). Over the next year, I’ll be using this blog to find out what topics interest people/have the potential to become online courses.


This is one of my newer pursuits, and one that is on hold while I travel. It interests me for a few reasons:

  • It’s a manual, tactile pursuit. Unlike all the other skills on this list, beer brewing is a physical activity that requires measuring, boiling water, microorganisms, and little bags of dry ingredients. So it provides some nice variety when compared to my typical computer activities.
  • It scales through different levels of complexity. It can be as simple as heating hops, grains, and water and letting the result ferment with yeast, or as complex as testing and adjusting the water chemistry before harvesting wild yeast. So there’s always something new to learn.
  • It touches on unfamiliar fields. You can’t study/practice homebrewing for long without encountering basic chemistry and olfactory skills. I’m hoping to use it as a gateway to learn more about science and gastronomy.
  • Beer is delicious. Nuff said.

Continue to read across a variety of subjects

My current interests include urban studies and automation/AI. Reading about these topics isn’t directly related to my business goals–it’s just a part of staying intellectually engaged and building material for later projects (such as a book, for example). I also want to start taking notes on what I read, as that’s a habit I’ve gotten out of (more on the importance of habits below).

Do more creative and personal writing 

That includes this blog, of course, but it also includes continuing to write creative non-fiction and personal essays. I devoted a large amount of time to this pursuit for my Senior Independent Study in college, and I don’t want to get out of the habit. This blog is the platform I will use for these endeavors.

The above is, well, a lot. But I’m a fan of setting ambitious goals (and following through on them with powerful supporting habits).

One important caveat: I reserve the right to change course as I pursue the above. That is, I don’t feel blindly locked in just because I’ve made this list. I view this list as a starting point, and I’ll let my curiosity guide me as I go along.

To conclude this section, here are some links to people and resources that have inspired me in my self-education journey:

  • Fluent Forever – If you want to learn how to learn a language, this book is the definitive resource.
  • CIG Learning Guide – The blog post that got me started on my own self-education journey 3.5 years ago. In the interest of full disclosure, I’m a writer for the site.
  • Pragmatic Thinking and Learning – A game changer for how to think about learning in the context of your career. A compendium of invaluable, research-backed knowledge.
  • Deep Work – Cal Newport’s manifesto one the necessity and reward of spending your time engaged in deep intellectual challenges.
  • The Power of Habit – Outlines a powerful framework for breaking bad habits and forming good ones.
  • Austin Kleon – A self-described “writer who draws”, he has a weekly newsletter that is my favorite source of creative stimulation.
  • Farnam Street – A good reminder that I’m not as smart/educated as I think.
  • Brain Pickings – The premier online home for the liberal arts.
  • Nat Eliason – The writer who inspired me to write about whatever interests me. His newsletter is superb.
  • James Clear – An early and continued inspiration in the areas of behavior change, entrepreneurship, and lifestyle design.
  • Scott Young – A key inspiration in setting ambitious learning goals.
  • Doug Toft – A critical influence because of his articulation of the “idea entrepreneur” concept.

Making It Happen

“Inspiration is for amateurs – the rest of us just show up and get to work.”

– Chuck Close, interview in Inside the Painter’s Studio by Joe Fig

All of the above are great to say, but the real challenge, the real power, is in doing it. It’s all too easy to go at a goal fiercely for a week or so and then gradually backslide due to inertia or boredom or frustration.

What I need, then, is a way to keep going. A framework for progress. A plan of attack.

Here’s my general plan:

1. Embrace boredom

When you start learning a new skill, everything is exciting. You’re making great progress, and anything seems possible. But soon, the high of these “beginner gains”4 fades. This is the most dangerous point in any learning journey. This is the point where you’re likely to give up.

They key to breaking through this stage is to embrace boredom. See it not as a cause for frustration, but as a sign that you’re on the right track.5

2. Get up earlier

This is my favorite solution to the issue of “I’m so busy working that I don’t have time to learn anything new.” Just get up an hour earlier. It’s easier said than done, of course. I’m terrible about sleeping way too late after having stayed up the night before fucking around on the internet. But that’s why I’m putting out the advice–so that I might heed it as well.

3. Set weekly learning objectives

The concept of setting goals is a tricky one. Scott Adams argues in How to Fail at Almost Everything and Still Win Big that setting goals is a recipe for disaster, since it puts you in a nearly constant state of failure. Instead, he advocates creating systems, since once in place they don’t depend on your willpower or your ability to reach a particular desired outcome

I agree with Adams that a solely goal-based approach isn’t the way to go, but I don’t believe in throwing goals out entirely. My current approach is a hybrid of the systems and goals approaches.

In essence, I have a general system for learning that I use to support specific weekly learning objectives.6 The system is Spend at least 1 hour each day actively studying Spanish. Into this system, I plug my weekly objectives. For example, Learn all the ways to express the concept “to become” in Spanish.

Generally, I set three weekly objectives related to my learning goal, making sure that each of these objectives fits the SMART framework.

4. Focus on one skill at a time

The other great challenge in learning new things and doing meaningful work is focus. With the list of learning goals that I outlined above, it will be easy to get distracted. So I need to pick one skill to focus on at a time…sort of.

My experience has been that it’s fine to focus on multiple skills at once so long as they’re sufficiently different. The best case of this I can think of is a physical vs. a cognitive skill. This is an unnecessarily broad distinction, but it gets the point across. So, for example, I think it’s fine to learn both rock climbing and copywriting at the same time, since they’re such different domains.

Furthermore, I’ve found that learning one skill for work and another for pleasure also fits together nicely. So, for example, learning both course creation (work) and beer brewing (obvious pleasure) simultaneously.

You could argue that I would learn either skill more effectively if I just focused on it and nothing else, but I find that neither practical nor interesting. I.e., it’s impractical to spend all day learning to brew beer (unless that actually is your job) and uninteresting to spend all day copywriting.

5. Maintain existing skills (or don’t)

When learning a new skill, there’s also the challenge of making sure you don’t neglect existing ones. Strength training provides an excellent analogy.7 It’s fine if you decide that you need to focus on increasing the weight you can squat…but not to the exclusion of all other forms of training. Doing so is a recipe for atrophy and injury.

Instead, you want to put your focus on increasing your squat while also maintaining your existing weights in bench press, deadlift, etc. This makes sure you’re well-rounded and don’t lose your hard-won progress in all the other lifts.

So it is for learning any new skill. The ease of maintenance will depend on what the skill is and what you use it for. For example, it’s very easy for me to maintain my writing skills since I write professionally. Something like playing the saxophone, however, requires more deliberate effort, since I don’t do it professionally and am not currently part of any musical groups.

And, of course, you may decide that some skills aren’t worth maintaining. They may no longer be relevant to your life (for example, skiing isn’t a particularly relevant skill if you live in Florida). Or they may require more effort/money than is practical. To use a personal example, I’ve stopped training rock climbing because I didn’t have easy access to a gym while in college and the local gym in Nashville is both expensive and a 25-minute drive from my house.

But for the skills that you decide are worth the effort, the key is to, well, make an effort. Do what it takes to make sure these abilities don’t atrophy.

6. Stay accountable

Accountability is a huge challenge with self-directed learning. When you’re in school, you have grades, professors/teachers, ongoing assignments, and (possibly) your parents and classmates to hold you accountable.8

Out in the real world, that built-in accountability system disappears. If you want accountability for achieving your goals (learning or otherwise), then you have to seek it out.

Of all the aspects of self-directed learning, I think that accountability has made the biggest difference for me. When I have it, I do things I never thought possible and make crazy progress. When I lack it, I sputter, stall, and ultimately coast down the slippery slope towards equilibrium.

If you really want “this time to be different”, you need accountability.

Here are a few of my favorite ways to stay accountable:

  1. Commit publicly. Whether it’s on social media or your website or on a whiteboard that your roommates can see, make your goal/objectives clear. This way, you’ll have people to call you out if you don’t follow through (or, at least, the knowledge that someone could call you out).
  2. Put something at stake. This can range from telling your friend you’ll pay them $50 if you don’t write 500 words per day to scheduling an embarrassing Tweet to go out if you don’t get up at a particular time. This technique is super effective because it leverages humans’ natural aversion to loss.9
  3. Find an accountability partner. Great for things that you can actually do with another person. So if you have the goal of going to the gym 3 days per week, get a gym buddy. It’ll be much harder to skip the gym when you know you’ll be disappointing someone else.
  4. Work with a coach. Accountability partners are cool, but sometimes they don’t work because both of you suck at sticking to your goals. In this case, an accountability partner can actually be detrimental. This is where a coach can be great. They can help you develop SMART goals/objectives, and they can ruthlessly motivate you–it’s their job, after all. Plus, since they don’t tend to come cheap, you’ll have a financial incentive to follow through.
  5. Use an app. In the past, I’ve used Habitica, Beeminder, and and Habit List to stick to goals such as waking up at 8 am, drinking at least 1 L of water each day, and meeting one new person each week. You can also adapt a task management app such as Todoist, Trello, or Asana for this purpose. It can even be a simple as putting a recurring event on your calendar.
  6. Combine the above. I’ve had lots of success with combining the above approaches. For instance, I’ve used Beeminder to charge me money if I don’t wake up at a certain time and worked with a coach to create public commitments. More accountability is generally better.

I’ll admit that while I’ve done all of the above in the past, I’ve lately been lax. So in writing this post, I’m publicly committing to changing that. I’m going to use my calendar to schedule skill practice at the same time each day, and I’ve already created goals in Beeminder to help me stick to daily JavaScript and Spanish practice. I’ll also be posting periodic updates on this blog.

7. Break out of plateaus with sprints

If you commit to learning anything for the long term, you’re going to hit plateaus. It’s purely a question of when, not if, so you should prepare in advance for how you’re going to break out of them and keep your progress trending in the right direction.

One of the best ways I’ve found to break through learning plateaus is to use sprints. Basically, you ramp up the intensity of your learning for a set period of time, anywhere from a week to a month. You pick a super specific goal to focus on, and then you go at it with everything you have.

So, for example, I’ve recently hit a plateau with learning Spanish. Even with the benefits of full immersion available to me in Medellín, Colombia, I’ve still found myself stagnating. I’ve gotten to the point where I can converse fluently about most subjects and navigate day to day with zero problems. Since I’ve reached this level, it’s easy to get complacent and comfortable.

I don’t want that, though. I want to go further. Specifically, I want to be able to follow live TV or movies without the help of subtitles, read more advanced literature, and learn to write blog posts in Spanish.

So, right there, I took the first step to moving past the plateau: I defined what would constitute further progress. This is absolutely necessary–you can’t just say, “I want to get better”.

But defining it isn’t enough. I have to DO IT. And that’s where the sprint comes in. For this sprint, I’m going to focus on reading, mostly because I have a big backlog of unread Spanish language books. Specifically, I’m going to read a poem a day from the collection Poetas Hispanoamericanos. And not just read it, but underline unknown words, look them up, and add them to a new Anki deck along with the line from the poem for context.

The details of your sprint will vary depending on what you’re learning, but the principle is the same: pick a concrete objective and go all in for 7 – 30 days. Rinse and repeat.

8. Review progress regularly

I’m not great about this, I’ll admit it, but when I do take the time to review my learning progress each week, I notice the difference.

Reviewing your progress doesn’t have to be long or elaborate. All you need to do is take 5 minutes to review the learning objectives you set for the previous week and ask yourself if you (honestly) achieved them.

If you didn’t, then write down why not. It’s fine if you didn’t achieve the objective you set–just be honest with yourself about why you didn’t and what you can learn from it. Whatever you do, don’t lie to yourself.

Bonus Tip: Keeping these weekly reviews in a spreadsheet is a great way to track your learning progress over time. Thanks to Stefano Ganddini for introducing me to this technique.

Endnotes: Life Learning

So far, this article has covered how to learn skills of one type or another. This kind of focused, self-directed learning is absolutely key, no doubt. But there’s another type of learning that people don’t talk about so much: the learning that comes from varied life experiences. Or, as I like to call it, “life learning”.

Life learning is harder to quantify than skills. That is, it’s harder for other people to observe and almost impossible for you to recognize in the moment. The value of life learning often becomes evident only after years or even decades.

So if you can’t know what life learning looks like in the moment, how can you plan for it? Should you even bother? While I don’t think you can know which life experiences will be the most formative, I do think you can maximize your exposure to life experiences that will probably be valuable.

Here are a few examples of how I maximize my life learning:


And this doesn’t just mean international travel. My current trip to Medellín is part of this, but it also includes my plans to live in Knoxville with my friends for 6 months, as well as future (vaguer) plans to live in other U.S. cities and my goal to visit all 50 states before turning 25.

Meetups and networking

Being involved in a community will teach you all kinds of things, if for no other reason than the diversity of people you meet. For me, this means going to local events related to my interests and seeking out connections with others in my field.

Nurturing existing relationships

As a recent college graduate, I’m at a point in my life where my friend group is naturally splintering. At least, splintering geographically.

Some of my friends are still in college (an 8 hour drive from my home city of Nashville), and the friends I’ve retained from high school (and I have the fortune to stay in touch with many of them) are taking jobs in other cities, going to graduate or professional school, and overall just moving on (and away).

So it’s all the more important that I nurture these relationships, stay in touch with these people, visit them every chance I get. Because good relationships are what matter in the end. (See also: #4 of the top five regrets of the dying).

Spending more time talking to my parents and grandmother

If there’s one thing all the musician and actor deaths of 2016 made me keenly conscious of, it’s that life is tenuous. As such, I want to spend as much time as I can absorbing the wisdom and enjoying the company of people like my parents and grandmother. While I still can. I don’t mean to be morbid; rather, I want to take life’s temporary nature as a reason to celebrate it all the more.

Daily walks

This is something I don’t do enough of, but I never regret it when I do. A solitary walk (or a walk with a companion who isn’t afraid of silence) gives your thoughts a chance to breathe. You take in the wonderful little details of the everyday, and you come to all sorts of epiphanies. If nothing else, you get some exercise.


If you made it to the end of this guide/manifesto, thank you. I had no idea I had this much to say on the topic when I started. Though now that I think about it, this article has been almost four years in the making. I hope that you found it valuable, and I’d love to get your feedback.

If you have any suggestions for improving this article or your own self-education experiences/questions to share, please reach out via my Contact page. Or, if you prefer, you can also Tweet at me.

  1. I’m a freelance writer and editor, writing articles on such topics as learning, travel, marketing, and psychology and editing nonfiction books for self-published authors. Get in touch with me about projects here.
  2. Mind you, I’m not saying that everyone can (or even should) aspire to high up leadership positions. But you should at least consider the value of learning and increasing your skills if you ever want to, for example, switch to a different company, change your career path, or get a raise.
  3. Arguably, everything you learn is potentially useful to your career, especially if you’re an entrepreneur or creative type. You never know what idea might be the trigger for something revolutionary.
  4. To borrow a term from strength training.
  5. I’m not saying that you should try to be bored, or that you shouldn’t seek to make your learning activities interesting and varied. Rather, I just mean that boredom will come at a certain point, and you need to accept that. Learning Spanish verb conjugations, for example, isn’t an exciting activity, but it’s crucial to eventually do more fun things like chatting with locals in a Colombian café.
  6. Thanks to Pragmatic Thinking and Learning for clarifying the difference between “goal” and “objective”. As the book puts it, “Just to be clear: a goal is a desired state, usually short-term, that you’re trying to reach. An objective is something you do to get closer to that goal” (157). So, really, it’s most correct to speak of setting objectives to achieve our goals.
  7. I’m definitely at best an advanced beginner when it comes to strength training, so please allow me the analogy while treating what I say with caution.
  8. Whether or not they hold you accountable for actually learning the material or just for completing the coursework is another question. But assuming you’re in school to learn (as opposed to just obtaining a certification or other piece of paper), I think the accountability still ensures that you learn something.
  9. Which is to say, given the choice between finding $5 and avoiding a loss of $5, we strongly prefer avoiding the loss. For more information on this cognitive bias and a thorough introduction to the field of behavioral economics, I recommend Thinking, Fast and Slow by Daniel Kahneman.

Leave a Reply

Your email address will not be published. Required fields are marked *