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#100DAYSOF - A Tactical Guide

What if I said in 100 days you could create major change in your life? Here’s how to pull it off with minimal strife in an hour or less. We address your #100DaysOf project one step at a time.



Creative Journey map by Lena Umezawa /

Creative Journey map by Lena Umezawa /

Habit is a GOOD servant but a BAD master.
— Gretchin Rubin

Got a bad habit to be late to the life you want to create? Make a habit of the behavior you'd like to emulate. Start by doing something small to progress every day and you will be well on your way to being the writer/author/speaker/teacher/genius that you already are. 

Want to hear more about Why 100 Days Matter? Read this. Otherwise, let's get to it. Maybe you want to start drawing again. Or write everyday. Well, let me be the first to congratulate you for committing. Now commit this to memory-- you're gonna want to quit. The following are 5 tips to keep you IN IT when the shit hits the fan.

I tell you the facts that no one told me when I embarked on my project, #100DaysOfCopyThat. It  would have been nice to know what to expect and find ways to not fight but dance with Resistance. Resistance is the force that will always show up whenever you attempt to level up in life. Pursuits in creativity, education, health, and career will undoubtedly stir up resistance, i.e., fear. So let's not stumble over the hurdles that it as well as life throws down, let's RUMBLE.


SOUNDS LIKE: “Ummm…::staring at blank screen:: this is hard and I think I have last night's dishes to clean...

YOUR MOVE: Push through. Trust me. Or tweet me. I’m happy to help keep your creative engine running. ’Cause after around day 28, the inspo will START FLOWIN’ and it WILL feel great.

Unlike toilet paper when the need is most severe, you will never run out of excuses why you can’t do your 'thing', m'dear. But if you’re like me and had ‘phone it in’ on speed-dial in the past then maybe JUST MAYBE you’re finally fed up with NOT getting anywhere than actually putting in the miles.

The Enthusiasm vs. Time Line Chart for a 100 Day Project

The Enthusiasm vs. Time Line Chart for a 100 Day Project


SOUNDS LIKE: “Hmm Is that [Insert Ex’s New Girlfriend’s Name] in those Maui pics? Is she a model?” Click, click click.

YOUR MOVE: Distraction-proof to prove you mean business. If you are writing, log into the ‘Guest’ account on your Mac if you have one or 'safe mode' in PC. Your attention is expensive--do not give it away for free. If you're social media prone, block it by using StayFocusd--a plugin for Google Chrome. A recent study by Digitrends puts checking social media feeds 17 times a day or more--so that's where a lot of our time is going--in my case, I have an Instagram 'bedtime' for sure.  At 10PM nightly, my alarm persists--stop flipping through Stories and give it a rest!

We can not prevent pitfalls or other peoples’ spills, we can not prevent fires--unless they're the forest-kind. Some we will always have to put out, although try and wait and let someone else use their water spout. What I'm saying is, when new habits emerge, they take time and energy and let's be real--there are VERY FEW REAL EMERGENCIES.

There are, of course, more important things in life than having a fully-activated creative mind. …like the health of your kid. I don't deny that and there may be legitimate reasons why you can't do it one time--just don't commit Habit treason. Miss a day? Add one on to the end, friend. And don't dawdle or worry...BTW your ex's new gf is not really a model. And by the way, by the time you look through all of her vacation pics on Facebook you could have been head down authoring the footnotes for your fabulous book. 


SOUNDS LIKE: “UGH. It's 11:49PM my work sucks and I'm pissed. I AM NOT putting this out into the world--not like this!”

Oooooh..yeah you’re right. Don’t put that out there. Blank stare... 

JUST KIDDING. In the words of Sheryl Sandberg: “Done is better than perfect.” Done will always be better--it's sustainable. Perfection is less than realistic--it's downright unattainable.

During my 100-day project, I copied something--with credit given--or added copywriting to an image for 100 days. Sometimes my posts looked like they were copied left-handed late at night. They were, except that's my dominant hand. I just couldn't get it down right. Others show the smudges, the trenches, the stenches of work-in-process. Even though it’s far from pristine, that’s what makes it interesting.

#100DaysofCopyThat / Day 27

#100DaysofCopyThat / Day 27

Some artists even go as far as to make the journey their end product. Cy Twombly's work is seen internationally, but I first saw it at the National Gallery of Art in Washington, DC. Many of Twombly’s pieces are scrawlings of math problems, colorful chicken-scratched color tests, corner doodles of faces with haunting smeared expressions. I was not sure if was his original intention, but the entire process was his work. The pieces were enormous, raw, wrenching and loud, and the coffee stains and punctures are narratives that rupture throughout. I try to keep Cy’s work in mind as I’m creating knowing that there is a way to show the behind-the-scenes without it going in the direction of teen center craft night, but sometimes shit happens and you still gotta ship it.

Think about it. When is the last time that you put something out there, work related or otherwise that was devoid of error, and pristine, the output exactly as you had imagined it? Yeah, that was likely a dream. There will always be the folly of time and human error, so might as well bare it.

OH, and important to note — no one’s looking at you. Very few will care (sorry). But you’re not doing it for them, nor likes hearts or shares. Which leads me to number four:


SOUNDS LIKE: “REALLY? SEVEN Likes? I just made the fricken Mona Lisa out of spaghetti!”

YOUR MOVE: Yes You did and it’s pasta-tively awesome. But before you go scratching your noodle about why you’re not receiving the kind of virtual love that your project should get, JUSTSTOP and keep going. You will keep making regardless. Hearts are not your fuel. And for God’s Sake, turn off the notification pop-ups--it's just cruel.

BUT, #protip: Do add the appropriate hashtags, especially the #100daysof[projectname] so that you are searchable and so that you can keep daily track of the game.

There is an exception to the silly-hearts rule and it's rooted in accountability. I started #100DaysofCopy that in the midst of my typography class, and my instructor was badass book cover designer, Jason Heuer. For at least the first half of the project, Jason ‘hearted’ every single one of my project's posts. Sometimes it takes just one person looking to help you through. That one little double-tap once a day did wonders for my confidence and resolve to continue.

Also, when you first begin and start talking about it, people will have either one of two reactions, “Oh hey, that’s cool.” Or “Good luck with THAT. I/person-I-know tried something like that before and lasted 2 weeks.” Yes, but they were weak--that isn't you. There will be resistance from the people you talk to. We as a species are resistant to change. But a funny thing happens when you are 1/3rd of the way this point, you have proven that you’re surious, and have no plans to leave the race. Suddenly you start to accrue a little crew of cheerleaders--sometimes and only including your mom--that really like what you got goin’ on. Use the momentum.


SOUNDS LIKE: “No way--there's an IG for farm-team athletic mascots? Jackpot. 

YOUR MOVE: Doing a project for 100 days gives you a reason to get in touch with people that are doing the kinds of things you’re into for way longer. They have experienced the hills and valleys of their craft and have battled resistance and made it back intact. Create a list on Twitter and keep tabs on them. Engage with them. Be useful to them, and you might find your future employer, client, or couch to crash on next time you’re in their town. Former living statue, musician, and author, Amanda Palmer notoriously has stayed in the homes of her fans while on tour. Throughout her chaotic creative career she has furiously dedicated devotees that will finance whatever endeavor she pursues next and will always open their doors.

Make things, ask the universe what is next, take notes, and share. This is a great way to live. Give this gift and receive humility, confidence, and find like-minds near and far. So now that you know what is par for the course, where will you go?

This is Part 2 of a 3-Part Series:

Part 1 — WHY 100 DAYS MATTERS.

Part 2 — WHAT to Expect on Your 100 Days

Part 3 — HOW to Find Your #100DayProject




silence the bitchy whisperer [i.e. Fear] deep within you with your skinny jeans on that says: “pssssh…you can’t pull this off.”

I am an expert at trying ‘a thing’ on for size, twirling around in it, asking a few people their opinion, and then finding some reason why it’s not for me--too tight, too high-maintenance, not short enough, or not FREE. I was desperate for a self-inflicted project to which I could commit. I was so sick of getting excited about a project and then just dropping it. Just once, I needed to be acquitted of THE QUIT.

Do you keep your side project at bay? Is there a calling that you keep letting go to VM? Or, actually, for me it is more like a tugging at my pant leg that I keep kicking away.

And then there are those people that are DOING that thing you want to do too. The ones that spark *ENVY*. The ones whose work you see that make you say I wish that was me.’ Or, ‘I had that idea in 2,000fricken3!’ Or, that creepy/vulnerable moment where you hear someone’s words and something in your chest shifts and it resonates within the caverns of your soul. That happened to me within the first few pages of Elle Luna’s Crossroads Between Should and Must, given to me by my friend, Missy, whom I loved, and trusted. Elle alongside the Great Discontent ran 100-day campaigns to help creative projects GET 'SENT.'

I read the book which got my inspired thoughts churning but I put the project on the back burner.

A few months later, an art director, Catherine Casalino, came and spoke to my SVA typography class which would banish me from a creative rut. She was doing #100DaysinWonderland inspired by the Lewis Caroll book and the iconic NYC designer, Michael Bierut.

I was intrigued. A Google search revealed that Bierut was behind the FedEx logo and the Saks Fifth Avenue seal. He was also an SVA instructor and had his students embark on a 100 Days Challenge on 11/7/07. It was November 5th--8 years later when I read that bit. I had two days to plan my 100-Day Trip.


It’s memorable, for one. And Jay Papasan, and Real Estate mogul Gary Keller show us in The One Thing that it takes 66 days to make a behavior a 'thing'. As creative people, our drive and resolve to make is met with an indefatigable force that create painstaking delays in delivering our craft to the world. So, think of those other 34 days in your trip as an insurance policy against failure-to-ship.

There is also proof that the first 100 days in an era can dictate overall success in an endeavor. Case in precedence--the gestation period of the newly elected presidents. Michael Watkins, in his HBR article, Why the First 100 Days Matters, explains why this 3 1/2 months is so clutch: “[Leaders] entering new roles can stumble badly and still recover. But it’s a whole lot easier if they don’t stumble in the first place. And that’s why the transition period matters so much.” 

It can feel daunting to embark on something that can feel as though it would claim entire nights, weekends, or precious time away from family, friends, and your 9-hour workday.

But what if you committed just 20 minutes daily? That’s half of an already-shortened lunch break or two showers, sans shaving. Imagine the calories and water you’d be saving! Seriously, though, the length of time will vary, depending on your piece, and can be way shorter like Zak Klauck’s 100 posters-in-a-minute project. We will get to what kinds of projects make a good fit later, but first, the other less worthy reasons for starting a project (other than squashing your fear that is).


Imagine that sensation of starting something new. Snowboarding, for example. Did you suck at it too? You can barely sustain momentum long enough to sneeze and lose balance. You used to have abdominal fortitude before you strapped yourself into a board and headed down what feels like an ice luge. Maybe you are with a few people on the slope that suck worse. That’s comforting for a minute but then WHURRRRRSHHHH….the pro’s whiz past you in a flash of color and sound. And they’re having the time of their lives. You? Dumbfounded. At least that is how I saw it when I tried snowboarding for the first time on the icy slopes at Hunter Mountain in NY with over-aggressive sunshine. Except those pro’s I mentioned before were actually 7-year-olds that come every winter with their fit European mum, dad, sis and bro. I could have phoned it in after my lesson as I had endured enough wipeouts on near zero-degree inclines to earn an adult hot chocolate in the lodge, fully reclined. That is where most of the other slope virgins in my class had gone. But what kept me from hanging with it and long after my comrades had hung up their bindings?

It was finding that feeling that when I did start coasting if only for a second, it was fun. It’s fun!

You feel a slight breeze. It’s thrilling and effortless; you forget that ache in your wrist and for a moment, you are in the flow and it’s bliss. It’s adrenaline, and pride, and excitation, and fear all served up in this flaming high-flying cocktail and you glide down the slope until BUMP, you’re down again. If only you could sustain that momentum for a moment longer, multiply it by 2, you just might make it down the hill before the trip is through.

It is similar with creative pursuits. You start making a thing, getting into the groove, and what you make isn’t that good at all. But you improve. It has good bones. And though you notice the Gap between what you’re making and what you want to make, the best way to get to where your heroes are is to JUST START MAKING. A lot. And the more you make on a consistent basis, the faster you fail and the quicker get to sucking less.


When I left my job in September 2015, I did not know exactly what I was looking for next. But I knew who I looked to that were doing things I loved the best. And what do you do when you discover something--or someone--you love? You get to know it. You sign up for their mailing list and read and research. Watch Youtube videos and drink instant coffee in graphic PJ pants with your socks pulled up. And then you attempt to emulate it, despite the suck. I admired the sharp-tongued wit of copywriter Ashley Ambirge, the vulnerable hand-lettered poetry of Debbie Millman, design thinker. And the principles laid out by best-selling author, Austin Kleon, in Steal Like An Artist gave me permission to tinker. That is when my project, #100DaysofCopyThat was born. And along the way, I discovered so many amazing artists and writers that blew my mind with their creative contributions I felt so blessed to find. And suddenly, we were connected through a shared appreciation of funny coffee mugs, ambition to expresso ourselves, or really awful puns (not a typo above:).


You will notice something strange when you start making every day. Inspiration starts to trickle at first...but then FULL-ON SPRAY. You can’t get the ideas down fast enough. And then the next day the mainline will be dry and rusted and you need to start scratching the surfaces of your swipe file. The swipe file is where you'll go when you start to pout that there is an idea drought.  Later, we will get into ways to safeguard your creative stash when this (and other pesky things called Life) come to pass, but I promise, the more you make, the flow will start to self-regulate.

If this revvs your engine to start your own 100 Day journey, stay tuned for the next installment — What to Expect, where I’ll lay out provisions to pack as you prepare for the days ahead in your creative trek.

Part 1 — WHY 100 Days Matters

Part 2 — WHAT to Expect on Your 100 Day Trek

Part 3 — HOW to Find Your #100Day Thing