Do More of the Work that Makes You Happy

Do More of the Work that Makes You Happy.

What does “Work that Makes You Happy” mean, exactly?

Over the past several years, I’ve had a chaotic and immensely exciting time as I’ve narrowed-in on increasingly fulfilling work.

But not before I spent some time pulling my hair out.

A few years ago, I found myself working at an ice cream shop. I had no college education, no formal credentials of any kind, and having graduated high-school with no concrete skills.

Fast-forward a couple years, and I’ve transitioned into the startup world where I’ve since been able to:

    Write codeLearn graphic designBuild email marketing campaignsCreate and execute SEO plansWrite press releasesDo sales calls with multi-million dollar clientsAnd jump in and out of all kinds of different roles as they popped up


In this post, I’m going to show you how I did it.

Of course, there will be considerable trade-offs: (a) free-time (you won’t have as much), (b) relaxation (you will be spending your energy), and (c) social life (who needs it, right?).

The degree and timeframe to which you decide to sacrifice these things will reflect the speed and certainty you can have that you’ll succeed in building more meaningful work into your life.

I’m quite confident that the short-term investment you make is worth it given the result is so extreme, but I’m also certain that you can’t expect this to fall into your lap.

There’s no doubt in my mind that anybody can do this, as long as they know what they need to do.

Before I begin, let me clarify what I mean by “happy”.

Most people loosely toss this term around even though there are multiple different types of happiness.

In this article, I’m not talking about simple stimulation (having fun) or contentment (nothing is going wrong).

I’m talking about a much deeper psychological sense of meaning and purpose. It comes from exercising your mind, or having a sense of forward motion toward a purpose that’s bigger than yourself.

This is basically just means “having fun”. It could be the result of riding a roller coaster or winning a big hand in poker. While this type of excitement can make you feel really good, I wouldn’t recommend relying on it for anything sustainable.
This is more of a “nothing is going wrong and life is great until the water gets too choppy”-type of deal.
is a much deeper psychological sense of meaning and purpose. It comes from exercising your mind, or having a sense of forward motion toward a purpose that’s bigger than yourself. It’s what great lives and great companies are built on. This is what we mean when we say “happy”.

So, what makes work more fulfilling?

According to Daniel Pink (who literally wrote the book on fulfillment—a New York Times bestseller called Drive), extrinsic motivation (money, bonuses, candy, etc.) doesn’t work.

Instead, intrinsic motivation is what matters.

Specifically, he focuses on:

The authority to do your work in the way that makes sense to you and matches your natural work cadence.
The sense that your work is contributing to something significant.
The feeling of growth in an area that matters (i.e. the acquisition of useful skills or knowledge)

This huge insight is one of the main reasons why I’m now doing work I love.

Let’s get started.

Becoming a learner

We’re going to add a bit of extra meaning to “learner” in this case because – assuming you’re like myself – you’re not always interested in learning things for no reason or in an inefficient way (this isn’t school).

Specifically, I’d recommend adding the following competencies to your definition:

One who learns only the parts that matter and skips the rest

One who learns as rapidly as possible

One who takes as many shortcuts as possible (again, this isn’t school)

One who learns things that have utility (i.e. creates value for other people)

With the obvious emphasis on speed, there’s one other concept I’d like to touch on:

Binge learning.

Learning in long, intense stretches is much more effective than small, comfortable increments spread out over several weeks.

The key is finding as much time every day to make progress in your subject of choice until you cross a certain threshold of competence.

My #1 recommendation is to wake up an hour earlier and start your day by learning the fun stuff during this hour.

This sounds like it wouldn’t be enjoyable, but it will become the best part of your day.

When you wake up early and start your day with enjoyable, meaningful motion toward your larger goals, you’re mind quickly begins associating these early hours with feeling good.

The instant this association is made in your subconscious, you don’t have to rely on discipline to pry yourself out of bed: You’ll begin your days eager to get started.

In my case, I had become an avid reader toward the end of school and spent every waking hour for several years (aside from the 25 hours/week I spent getting rent/food money) diving into books on every skill that caught my eye.

I was blown away with how much there was to learn and how many great insights I was able to collect on a daily basis.

Over time, I supplemented the reading with practice which made me much more useful and gave me the ability to add real value – but I had no way of proving to anybody that I knew anything useful.

This brings me to…

Just Do It (and Get a Track Record)

Generally, you can break learning into (a) off-the-job (learning/practicing at home or in your free time) and (b) on-the-job (learning by working on real-world projects where the result matters).

After forfeiting a prestigious career as an ice cream scooper, I joined a company where I’ve had the immense luxury of working with a small team of very talented people where trust has never been an issue. In environments like these, it’s extremely easy to find opportunities to learn cool new things in a way that delivers real value to the company at large and forces you to learn faster than if you’re just building up your fundamentals.

When you have a primary role, you can – if you pitch it properly – spend your down-time/free-time contributing in ways that allow you to refine new skills by applying them to real-world projects.

Something I highly recommend everybody do (even those with no aspirations for compelling work) is to think really hard about the work you’re doing and find ways to cut down the time spent on anything you don’t like doing.

Aside from the obvious benefits, you would be shocked at how much time you’re able to open up by doing this. Adding an extra hour a day (from thin air!) has a HUGE effect.

Learning on the job is a “trial by fire” approach and isn’t always pleasant, but you learn fastest when your reputation is on the line and your output is being measured by it’s real-world value (not by how good you speculate your work is).

Your #1 asset when learning something new is that you can be cheap or free which makes it easy to outbid others for a specific job/role.

The best part is – assuming you have enough income to survive from your primary job – not getting paid doesn’t matter. You’re getting paid with (a) experience, (b) track-record (this is how you can get past not having any formal credentials for a skill – a great portfolio of work and a killer recommendation is much, much better than a college degree), and (c) the opportunity to do fulfilling work.

Without this luxury (i.e. if your company has a “minimum” that they can pay) you’re out of luck and it’s going to be much harder to pick up these skills in a real-world environment.

However, the more likely concern that is likely already in your mind is:

“What if my boss won’t let me? Because he never would…”

Ah, I can hear this objection coming a mile away.

In reality, this is quite likely to be the case. However, even though learning something within your existing job is the best-case, it’s never your only option.

The much more common (and reliable) approach is:

Learn 100% on your own until you can create real value with the skill (this is probably your best bet regardless)

Find people looking for this skill on a low-budget (find them via Google, ODesk, reach out of friends/etc.) and offer to do it for free (emphasizing that they’re welcome to not use it if they don’t like it, and that you’d be happy to do revisions).

This is basically a “take initiative and make your own job – even if you don’t get paid for it for a while” approach.

This, again, lets you build up the experience/track-record in a way that gives you leverage to either (a) continue finding clients/seeking referral clients (referrals are the #1 source of clients for most professional freelancers) which you can begin to charge for overtime or (b) return to your boss/team and show them your work and make an offer that makes clear that it’s worth their time to let you do it.

The bottom line is this…

Don’t wait for somebody to hand you the opportunity to learn something. Just start learning and find ways to use it to create real value for people.

It’s not always easy to do, but it really is that simple.

Part Four: What skills should I learn?

This is perhaps the most asked question I hear in my day-to-day life, and it’s one of the hardest to answer.

The reality is that you should be responsive to what people need (i.e. what skills are in high demand today—and likely to be so tomorrow) and very self-aware so that you can find alignment between the following:

What people need done
What you like to do
What you’re good at doing
What is easy to learn

I would argue that #3 is the least important, as I’m in the camp that with time, you can get good at whatever you want.

Keep in mind that #4 doesn’t mean that the learning curve is 2 hours—it means that the resources (books, YouTube videos, articles, tutorials, etc.) exist in troves and that you have immense access to the lessons that pros have spent years learning.

Some concrete examples of #4 would be:

Programming (PHP or JavaScript, in particular. Regardless of any complaints about these languages, there are more tutorials online than you could ever read)

Graphic Design (i.e. Adobe Illustrator and Photoshop)SEO (how to get websites to rank highly within the search engines)Web Development (HTML/CSS, WordPress)Copywriting (writing sales pages, emails, product pitches, etc.)

My #1 piece of advice to you is to spend time reflecting on what you enjoy—building things, exploring creative problems, communicating with other people—and find alignment with a skill that can give you satisfaction.

Once you know what you want to do, don’t stop moving forward until you’re in a position where you’re able to do more of the work you love.

Note: Check out our ultimate guide on how to be more productive for more tips!

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