The Complete Guide to Making It All Up As You Go

(EDIT — the above image is from I mistakenly used it without attribution, and the author reached out with complete respect and asked me to correct the error. Since I hate when people pass off my work as their own, just changing the caption on this photo didn’t seem like enough

Also, as it turns out, I really dig the product.

Also, that kind of goes along with the theme of this article.

Happy accident.)

I remember the split second it all unfolded — her raised right eyebrow, lips that puckered and closed as she finished the sentence and her vocal inflection rose, breathing life into the killer question mark.

14 heads turned from her to me, waiting.

The proper answer to her management question sat somewhere buried in a pile of manuals and procedures. No doubt it held an excellent analogy which would explain exactly what she needed to know.

I didn’t have that manual. So instead I did something unthinkable.

I made up an answer.

Let me ask you a question:

Do you have a 10-year plan?

You know, the one where each step is meticulously plotted out like dots on a map?

  • Married at 25
  • Startup created at 27
  • Millionaire at 30
  • Kids at 31
  • Philanthropist at 33
  • Retired at 35

Yeah, that one.

Let me ask you another question:

How many times has life unfolded exactly the way you imagined it in your head?

Many people think ad-libbing is a magical talent held only by the best actors and storytellers and con men. A superfluous trait only to be laughed at on television or enjoyed from afar.

But I’m starting to think it’s accessible (not to mention necessary) for every student, mother, and executive to deploy in everyday life.

Think of the best conversation you’ve ever had. Did you bring notes for it? Did you even know you’d be talking with that person beforehand?

Life is unpredictable. And improv actors know this. So they give in. They trust what will emerge from complete surrender will be better than any agenda.

In fact, it will likely be better than anyone could possibly plan.

Allow yourself to die

“You die in the improv set 5 times out of 9. When you get over your fear of dying, nothing really scares you anymore.”
— Bill Murray

My coworker was stammering, staggering, and shuffling through her stack of notes.

The script spelled out exactly what we were supposed to say to the audience, and she swore to follow it. She looked down every 30 seconds just to make certain she’d told our group everything they needed to know.

Until we got to Section 3.

“Where are the notes for this part?” she said in an urgent whisper while the class broke into a group discussion.
“Oh right, we’re doing it in a different order. I didn’t print those off.”

I quickly explained what the section was about, gave her a story to tell, and shooed her back in front of the crowd.

Terrified, she stepped forward across the abyss. The safety nets had been removed. She spoke from the heart. She used her words, not someone else’s.

Guess what happened?

The energy was higher. The crowd was more engaged. She acted natural, not like someone trying to stick to a script.

All because she allowed herself to let go.

You’ll be amazed what you can do when those comfort blankets disappear.

Ditch the map and get a compass

The idea of a “calling” as it’s traditionally messaged — one job which you do for the rest of your life — is a little outdated.

There could be a reason you haven’t found your dream vocation. It might not exist yet.

Here’s an interesting exercise to try: make a list of all the jobs you consider yourself a “good fit” for. These should be titles: “Engineer,” “Project Manager,” “Graphic Designer,” etc.

Next, make another list of the skills which fit in that job. They can be as vague or technical as you like: “Adobe Illustrator,” “Strategic Marketing,” “Ability to move heavy things,” etc.

Then, rank each of those item from highest to lowest as far as attractiveness. Sure, you may be interested in a bunch of different things (I am), but be honest with yourself. What speaks to you the most?

Finally, take the top three items and ask yourself why they draw you. The first time I tried this exercise, I started with “technical writer,” “novelist,” and “copywriter,” and whittled my way down to one simple thought:

“I love communicating ideas.”

That’s my true north.

This process takes only a few minutes, but helps you know yourself better. After orienting, you’ll see a universe of options you’d never discovered on your initial sheet of jobs.

(P.S. I highly recommend a book called “The Instigator’s Compass,” by Srinivas Rao. You can get it right here for the price of an email address)

Know your craft

If I was trying to “just wing it” when it came to cooking dinner, I’d fail miserably. Why? Because I am not a cook. I don’t know what tarragon is and whether or not you should mix it with brown sugar.

You might be though.

Whatever you do in life, do it with gusto. Learn what you love and go all in.

The more familiar you are with your craft, the less you need to prepare. (Actually, after a certain point, it becomes detrimental to prepare much because you can psych yourself out.)

“But Todd, I don’t know what I love! I’m not good at anything.”

If you’re saying this, it’s completely fine. We all start there. Want to know what the solution is? Do something. Anything. Think of 10 things you loved as a kid and start there.

Better to be confused and active than assured and stagnant.

Embrace the genius within

“Talent is hitting a target nobody else can hit. Genius is hitting a target nobody else can see.”
— Arthur Schopenhauer

My friend knows music. He knows it up, down, backwards and sideways. With a glance, he could tell you within $5 of how much an album is going for on eBay based on it’s age, title, rarity, and condition.

He is a collector at heart.

But for 40 hours out of the week, he takes a commute he hates, goes to a job he hates, and works with people he hates.

This breaks my heart.

It breaks my heart because work is more than a 9–5 drudgery. It breaks my heart because a bargain hunter can make a killing online with a little effort up front.

Most of all, it breaks my heart because he is completely unaware of what an incredible talent he has. Instead, he trudges to work week after week,

The reason you need to ditch the map is because the location you’re looking for might not exist yet.

Could it be possible, as wild as it might seem, you have a combination of skills nobody else has?

If there is even a distinct possibility of this, might it be worth a dip into uncharted waters?

Get comfortable in your own skin

I don’t much care to be shoehorned as a self-help writer, so I’m not going to pump you with 10 paragraphs about loving yourself.

Instead, here are a few practical tips you can start right now to get better at accepting who you are. Whether you are a photographer, manager, executive, or janitor, these three things are killer for improving your presence:

1) Talk to yourself in the car

Podcasts and audio books on 2X is all well and good, but if you are not processing what you learn, what’s the point?

Try this challenge: listen to just one podcasts in the morning. On the way home, open your voice memo app and recap the morning’s lesson. Try to come away with 3 major points that were discussed.

For bonus points, once you have those points identified, state EXACTLY how you can apply them to your personal situation.

(By the way, if you keep blanking on the lessons at the end of the day, it’s quite possible the podcast is simply not worth listening to.)

2) Post daily on

50% of all human communication is transferred through vocal tone.


That means you’ve likely been missing half of what anyone is trying to tell you if you’ve been operating only through email and text for a while.

Frankly, Anchor is a breath of fresh air. After 10 minutes there, you’ll feel like everything else you do online is in some sort of weird, phony cage.

Anchor is an overwhelmingly positive community full of people who love new thoughts, new ideas, and new viewpoints.

(And no, they don’t pay me to say any of this)

3) Talk to a camera every day

It’s odd how we humans are simultaneously mesmerized and repulsed by our own reflection.

If you’re ready to take step 2 up a notch, crack open Snapchat and commit to posting a video of you saying something every day.

Sound obnoxious? Scary? It won’t be for long.

Reminder: When you start, you will hate everything. You will hate your hair. You will hate your ears. You will hate your nose. You will re-record every video at least 14 times. You will give up or skip a day at least twice in the first week.

Push through.

When you see your reflection, you won’t see perfection. You’ll see something even better:

Something inimitable.

A final thought:

Life isn’t always about making the right choice. (Often there are no “right choices.”)

Instead, it’s about picking a path which piques your interest, starting forward with confidence,

and making the rest up as you go.