The Fear of Beginning Again

In his book So good they can’t ignore you, Cal Newport systematically (and often humorously) builds a case against the popular career advice of following your passion. In its place, he emphasizes the importance of building creative skillsets for success and finding the work that you love along the way.

This professional advice makes a lot of sense for anyone who is building a career from scratch. But during a recent re-read of the book I found myself asking…how might this advice change for people who are at an inflection point in their career, not the beginning?

Think about it. What’s the last time you were truly a beginner at your professional craft? Honestly, try to remember. Close your eyes and think back to your earliest attempts at whatever you do for a living today.

If you’re like 99.9% of humans, you weren’t instantly good on your first try. In fact, you kinda sucked at it. But if you got good, you did it like everyone does: through deliberate practice (one of Newport’s key strategies) applied over time.

And as time passes, if you continue practicing, you got even better.

But what nobody talks about is what happens when you forget what it’s like to be a beginner.

But what nobody talks about — including Cal — is what happens when you forget what it’s like to be a beginner. About what happens — psychologically speaking — when an “expert” chooses (or needs) to become a Beginner Again.

The Beginner Again inflection point

It turns out that I have a somewhat unique vantage point that has allowed me to witness this inflection point first hand.

Every year for 8 years, my partner Amy Hoy and I have taught a business course called 30x500 to hundreds of creative people — many are talented designers and developers. Their objective is to switch from employment & consulting into making some or all of their living from an asset-based business. In industry-speak, how to transition from services to products. In our own parlance; “Stacking the Bricks.”

But our curriculum isn’t the centerpiece of this story. It’s merely a backdrop for our students’ experiences. You see, our students are creative people who are at the top of their game professionally. People who are well educated, even better versed in their skill or craft. People who are often top earners in their field.

Our students enroll in our class by their own choice, committing hard-earned dollars to invest in their professional future. They watch their fellow students learn and practice and make visible progress. They thought that achieving their goal was possible — arguably probable — all they had to do was try to follow the steps we laid out in the curriculum.

I’m bad at this new thing

They’d make excuses, anything to procrastinate putting in the work. They’d fall back to old habits. In the worst of cases, they’d vanish completely. I’m talking about intelligent, curious, often proudly rational people who are capable of something many are envious of: creating things with their existing skills. But when these creative pros sat down to learn a new skill from scratch, where very few of their existing skills translate, they lose their freakin’ minds.

Take note of this last part: where very few of their existing skills translate.

This is especially painful when creative people internalize their creative work as part of their identity. The fact of “I’m bad at this new thing” quickly becomes confused and conflated with a more emotional “I’m bad.”

When you have very few (or none) of your proficiencies to anchor you in your expertise, it can feel anywhere from disorienting to paralyzing.

For many experienced professionals, it’s been so long since they’ve truly been a beginner that they forgot what it feels like to be bad at something. When you have very few (or none) of your proficiencies to anchor you in your expertise, it can feel anywhere from disorienting to paralyzing.

And, paradoxically, the more high performing you are in some areas of your life, the worse this effect can be. Because as you can imagine, thinking “I’m bad” is not a productive mindset to be in when you’re trying to learn something new, even if you rationally know that it will improve your creative career.

Getting past the Beginner Again inflection point

Through all of our revisions and improvements to 30x500 over the years our student success rate continued to climb, but every new class came with a new wave of Beginner Again anxiety.

That’s when we decided to use our ability to anticipate this anxiety to help our students get through it. Here are three lessons that we teach our students to help anticipate the feelings that come with the Beginner Again inflection point, and power through:

1. Know what’s at stake.

Isaac Newton got it right: an object at rest stays at rest. Same is true of people who have successfully built a career for themselves where they’re comfortable with their stay in life.

The problem with comfort and complacency is that it’s a safe haven for those moments where the Beginner Again inflection point is most painful. Rather than push through, we rationalize our way back into our comfort zone. To get through the inflection point, we need to recognize that complacency is our worst enemy.

To get through the inflection point, we need to recognize that complacency is our worst enemy.

In your moments of transitional weakness, when you’re most likely to retreat back to comfort, you need to be able to remind yourself of the reason you’re on this path in the first place. Why bother? What’s at stake?

Maybe your idiot boss just gave you another impossible deadline. Maybe you just missed another of your kid’s soccer games because you had to stay late at the office. And not just professional goals! Maybe you couldn’t squeeze into your favorite pair of jeans this morning.

When this pain momentarily bubbles to the surface, it’s much easier to get motivated and into action. Those are the moments when we say “I’m really going to quit” or “I’m really going to start going to the gym.”

But when the external pain subsides, it no longer outweighs the pain of doing something new and kinda scary. So you stop putting in the work.

To power through the Beginner Again inflection point, it helps to keep your pain visible. It’s a little bit counterintuitive (and maybe a little bit masochistic), but it does work to keep you going.

“Another impossible deadline”

“Missed the game”

“Can’t button my jeans”

Write yours down on a post-it note. Stick your note to the edge of your computer monitor or the vanity mirror in your bathroom or next to the speedometer in your car. Do it in your own handwriting, so it’s unmistakably a note from you. Some people like to take a screenshot of the note and save it to their phone’s lockscreen.

Wherever you put it, make sure that you have it visible for those moments where the Beginner Again inflection point has you considering a retreat to your comfort zone.

2. Understand what’s behind your questions (and make sure they’re really questions!)

A lot of the pain of being a Beginner Again comes from having questions that you can’t answer. Experts are used to having the answers, or at the very least knowing how to find the answers.

That sense of certainty is shattered when you’re just starting to learn something new, which makes every new question feel a lot bigger than it really is.

Two kinds of questions are especially common:

Question One: Am I doing this right?
Being a beginner almost always means trying things that don’t feel “natural.” But there’s rarely more to that feeling beyond the fact you’ve never done it before. We over-index the feeling of “I’m going to screw this up!” …before we’ve even tried to take the first step.

So when a question or uncertainty pops into your mind, take a moment to see if you have the ability to answer the question yourself. Write it down, and maybe even sleep on it for a night and see if you still feel the same way in the morning. You might realize that you already know the answer!

If your question is keeping you from trying, ask yourself: “What’s the ACTUAL worst case scenario if I don’t get this 100% right? Will I still make progress if I get this only partially right? Could I try this to see what happens, without putting myself or someone else in harm’s way?”

In many cases, 10% “right” and 90% “wrong” is still better for progress than doing nothing at all.

Question Two: “What if…?” 
It’s smart strategy to think a few steps ahead, like in a game of chess. But more commonly, creative people let their imaginations run wild and come up with all kinds of questions they MIGHT need to answer in the future. “What if…” questions are based on a theoretical scenario in the future that hasn’t happened to you yet, and is unlikely to happen terribly soon.

What if I use the wrong kind of wax on my spare Lamborghini?

Amy and I like to call these “What color should I paint the 9th bathroom in my mansion” or “What if I use the wrong kind of wax on my spare Lamborghini?” questions… because they’re questions that don’t matter until you get a mansion with 9 bathrooms, or have a spare Lamborghini… and you should be so lucky.

Don’t let imaginary scenarios that are MANY steps ahead of where you are keep you from doing the work to move forward today.

3. Use tiny wins to build momentum.

One of the biggest (ha!) mistakes that I see people make in all aspects of their work how they calibrate their expectations. This is especially dangerous territory for experts becoming a Beginner Again. We start out excited, even though we suck. Remember, it takes time and deliberate practice before we start to feel like we’re “good” at it, whatever it is.

If we don’t get good enough, fast enough, frustration starts to set in. Kathy Sierra calls this the “suck threshold.”

Image credit: Kathy Sierra, Creating Passionate Users

Notice something? That gap between the Suck Threshold and the Passion Threshold….that’s right there is the Beginner Again inflection point.

To get through the inflection point, you need momentum. And nothing builds momentum like trying something and succeeding the first time. Sounds obvious, right?

Then why do so many beginners start by setting their first bar unachievably high?

When your existing skills don’t translate to a new domain of expertise, you can’t set your expectations based on your past performances in other domains.

So what do you calibrate expectations from? Tiny wins today.

The trick — if you can call it a trick — is to design your expectations to be “upward” from where you are now… but where the odds of success is statistically in your favor.

Stanford professor and director Dr. BJ Fogg has spent 20 years studying human behavior, and asserts that any lasting change is most likely to be created by starting small — like flossing a single tooth, or doing one pushup a day.

Need help figuring out the right size for your own tiny wins? BJ offers a completely free one-week program every week that we’ve referred thousands of our students to, and is one of the best primers on the subject.

How to be a Beginner Again in any part of your life

I learned a lot of these lessons while teaching people how to shift from service businesses into selling products, but the Beginner Again inflection point shows up any time your existing skills don’t translate to a new pursuit.

  • A new job or promotion — people who are promoted to the level of managing or leading teams find themselves needing to learn an entire new skillset.
  • Artistic or creative skills — drawing or painting, playing music, even learning to write code all feel scarier to learn from scratch the older we get, in part due to our fear of being a sucky beginner.
  • Public speaking and writing — countless high-performing creative people fear public speaking worse than they fear death. And you might think you need to start writing 2000 word missives like this one to get started. You don’t.
  • A new sport or activity — I hired a trainer in early 2016 and found myself using these techniques to get through the rough early parts of changing my fitness routine.

Really, the list goes on and on.

Any time you’re starting something new where very few of your existing skills translate, you can use any one of these lessons, or all three in tandem:

Know what’s at stake. Understand why you’re questioning yourself (or the process) and start with tiny wins.