How to Brush One Tooth


Portrait of me, planning my wedding last week. 

Return from your bachelorette party sweaty, sleepy, and with depleted serotonin. Hug your man. He’ll suggest you take a seat and say he has some news. After a blissful 48 hours swimming and sipping wine, the worst you can conjure is that he neglected to water the garden.

Ask “are the tomatoes OK?” like an idiot.

He’ll shake head and tell you that the your wedding venue had been purchased by a developer. You need to find a new venue in less than three weeks. The news arrived in a few sentences along with a check for your deposit. Hope it doesn’t bounce.

Cry for a bit. Then take a breath and welcome the fresh opportunity into your lungs.

It’s not that you love planning weddings. Wedding planning feels like work. You haven’t yet recovered from the years of fundraising and galas. No, this is something different, you have been given a chance to exceed expectations. That is something you relish.

This is where you thrive. When expectations are lowered, you can catch the wind as it shifts and then you soar.

Cancel your meetings for the next day and spend the day planning a new wedding. Spend the afternoon visiting venues, rewriting your menu, and re-imagining decor. Enter a state of flow as you efficiently knock down several major decisions in a few hours. Discover that it’s not really that hard once it doesn’t matter so much. By 9 pm, you’ll be signing new contracts, cracking your knuckles and feeling the planning muse return to you after many months of struggle. This may carry on for several days. Coast on this momentum as you crank out emails you’ve been avoiding for weeks. 

My brilliant friend Darren at shared with me B.J. Fogg’s small habits philosophy, which we have nicknamed “brush one tooth.” Fogg, a Stanford Psychologist, suggests that lowering the bar by starting with very small habits, changes, or goals, such as flossing one tooth, increases longterm success. Of course, you’ll never floss one tooth. Once you get going, you’ll find it’s not as bad as you expected. The psychological barrier to creating a habit or starting a project is often greater than the force actually required to execute. When we think of the task as something small, we can get the ball rolling and then before we know it we’re flossing all our damned teeth.

This is what we do, as procrastinators. We lower the bar so we can soar above.

How do we harness this power we have, to lower expectations?

Brush one tooth.


Portrait of me, planning my wedding this week.


Gym Class Grit

I’ve been feeling a squeaky lack of grit lately.

Grit is one of those critical 21st century innovation economy traits. Grit is the ability to roll with the punches. The important human ability to take failure and adversity in stride. It’s the difference between staying on the mat and coming back swinging. You don’t go far without grit. It’s a strong predictor of long term success.

How do we get gritty? That which does not kill is makes us gritty. We become immunized to adversity though exposure. When we learn we can overcome a stressor, we develop an antibodies to tackle it again at a later date.

The alternative reaction to stressors — phobia and risk aversion — can be a major barrier, because risk is a necessary precursor to reward.

The success of serial startup founders can often just be a numbers game. Fail enough and you’re bound to get it right.

So, on the one hand, we have a Seth Godin or a Elon Musk, and, on the other hand, me, afraid to apply for jobs because one time I was rejected from a dog walking job.

In my counseling theory class this week, the professor discussed the fine line that parents must walk between inoculating their kids to stress and totally traumatizing them.


Behaviorist believe that all behavior is learned and can be unlearned. Which means I can develop grit. Someday, we’ll have grit retreats and grit camps for people of all ages who need some help acclimating to failure and adversity.

Someday, while building muscle at the gym, our strength training will be emotional. Alongside the 10 pound weights and fit personal trainers, there will be harsh personal critiques and catastrophic failures.

You heard it here first, kids.

Is Delaying Gratification Bad for You? (No, No it’s Not)

Betteridge’s law of headlines says that “any headline that ends in a question mark can be answered by the word “no.”

No. Delaying gratification is definitely not bad for you. Walter Mischel’s Marshmallow Test of willpower continues to be upheld as a strong predictor of long term success.1

This evening, I picked a gluttonous handful of herbs for a single-serving salad. Easily $4 at my local grocery store. I felt so wasteful. Nagged with guilt. Why? This fist full of flavor cost me nothing. In fact, I know that picking my herbs encourages growth. I know this intellectually, but it feels like if I’m picking them at all, I should be doing something more than making myself a really good salad.

Prune to encourage growth.

It truly took years of gardening (poorly) to accept this fact.

My tendency towards “saving” is illogical, but it feels so sensible. I make myself sick eating other people’s unwanted pizza crusts not because I like them, but because wasting food is bad. In college, I lived entirely on discarded food from the restaurants I worked in because it saved money on groceries (which then went to beer). I haven’t listened to the last 10 episodes of my favorite podcast because I’m “saving them” for when I “really need them.”

I also do this at work… and with work.

Today at work, I threw money on the ground and left it there. I have spent the last year playing protective mother hen to the only 20 copies of “the book2” in existence. My co-author was allowed to have 4 copies, our Executive Director got 3 and I have toted my one copy to so many meetings that it’s practically falling apart. This week, we made some updates and did a second printing of 100 copies. As I went to check how many were left of the first printing, I was horrified to find 12 crisp, untouched books left in the box. How many times had I gingerly taken the book out of an the hands of an interested party when I could have said “keep it?” How many hours of my life had I wasted dabbing at the coffee stain on the back. Ok, only one hour, but it was an important hour. As I pulled them out of their box and onto the shelf, I stopped caring. A precious copy fell to the ground and I just left it there. It’s worthless now.

For years, I stayed in a job I no longer loved and that did not pay well because I worried that I might not be able to find a job I loved more or one that paid as well. It’s no secret that I’m a scaredy cat3, and I really convinced myself I was doing the sensible thing.

Staying in a career you’re unsatisfied with will cost you money. Changing jobs every 3-4 years may lead to steeper salary increases. Forbes has a lot to say on the subject. While there are a lot of articles referencing precious little data, the data shows that switching jobs is likely to double your annual salary increase. The Blogosphere recommends changing jobs every 4 years for maximum salary and growth. Long enough for most people to fall in love with you. Not long enough to realize your fundamental flaws.

tenor (1).gif


1. This Atlantic article argues that income is a third variable. Isn’t it always? Inequality begets inequality.
2. I co-authored a book. It’s not as cool as it seems because we’re paying buckets for every copy we self-publish and also just giving them away.
3. Ooh! New blog title?.
4. Better blog title: “Writing the advice I need to take.”
5. Most of which comes from recruiters.

No New Feelings

In college, when I had “writers block,” I would open a word document called “noties.” Noties was like a private digital scrapbook for the era before ubiquitous social media. “Bits and scraps of shit, beginning Nov 2006,” is how it introduces itself.

It started as a place to record the things my friends said that I thought were just so deeply profound. I was 18 and living your own life for the very first time. I was obsessed with my friends. As a twin, I’d shared everything growing up, including friends. My college friends were smart and cool and weird and just mine. Talking in a circle with my friends on the floor of my dorm room felt like a sacred ritual. Their every clever utterance was poetry to me. Many of them were actually poets. Mostly they were just drunk.

I held myself up
By porcelain
And I had far too much to drunk

(CW, 2006)

I collected all sorts of things in my digital scrapbook. Scraps of sentences I overheard. Phrases I read. Odd sentences from junk mail. Anything that struck a cord or felt… deep. Dreams lived here. Dreams about boys. Music I listened to while thinking about boys. All the feelings. It didn’t feel like a journal so much as an alter to my feelings.  This is the home of my naval gazing habit.

After a few pages the scraps of thoughts start to form into poetry and prose. And the habit makes sense.  I was catching my tears in a jar as an offering to the muse.

I started to think of this document as a fertile riverbed of writing ideas. Then I started harvesting way too much. Were this a physical  book, it would be worn to shit. Eventually, there was nothing good left. This must be how humans felt before we agriculture. Like. Shit, if only we could figure out how to put these things in the ground on our own.

By senior year, I was sitting in a coffee shop with a friend, staring at a blank page and a rapidly approaching deadline, searching my Noties document for the start of something. After an hour he said “wouldn’t your time be better spent thinking of a new idea?”

Habits are hard to break. I still open the Noties doc for a stroll along the banks, searching for an idea that might have been overlooked.

Last night I slept and
Dreamed of

This is getting old.

(Excerpt from “826 dreams about you,” 2007)

Double Dutch

double dutch 2

I’ve never made a habit of jumping rope in public. My heart race increases when I remember the feeling of waiting to jump in to the ropes in double dutch.

I remember rocking back and forth, watching the rounds tick past and my friend’s facial expressions go from encouraging to embarrassed to annoyed.

What exactly was I waiting for?

The ropes didn’t get slower or lighter as the seconds pass. The odds of failure didn’t decrease. I definitely didn’t get any better watching the ropes pass.

The longer you wait the less fun it gets.

double dutch

So why wait?

I always wanted to be the kind of person who kept in straight away.

The last time I checked in here, I had jumped into the ropes. I jumped into a Masters in counseling after a friend applied and reassured me that it was easier and less terrifying than I expected.

And now I’m jumping rope for the foreseeable future, spending two nights in classes with *gasp* homework.

I’m happy to be in the game. I love school. I even love homework.

Indecisive people and procrastinators may understand the complicated delight in reviving a syllabus with weekly deadlines.

I’m remembering now how hard it is at first do or think about anything else while you’re jumping that incessant beat.

With practice, though, it becomes just another step.


Rock Bottom and Charting the Line Graph of Change

I know this guy who died once. He was depressed, an alcoholic, not taking care of himself. He fell into a diabetic coma. After a month, the doctors called it. They told his parents it was time to let him die. I mourned with his friends the night they pulled the plug. He was so young, we said. An important reminder to take care of yourself, we said, as we got drunk in his honor.

Then he woke up.

A few months later, I was sitting with him on a Chicago porch. I drank beer while he crushed La Croix. After the coma, he told me, he’d quit drinking, started taking his career seriously, and professed his feelings for a girl he had liked for years. Now he was sober, successful, and in love.

Rock bottom, I presumed. Not exactly. He smoked a big fat bowl as soon as he could. He felt like he felt he could have kept going the way he had before, with some obvious changes to keep the grim reaper away for few more years.

But he also realized that this was an opportunity that he didn’t want to lose. He had a choice: he could continue on his current trajectory, or to rewrite the formula. When he chose to get sober, it wasn’t because he saw clearly how his addiction was a barrier, or for the first time saw how precious life was. He knew, however, that he didn’t want this event to be an outlier, a blip. He wanted to take advantage of the momentum in his new, unexpected life.

We talk about rock bottom as a fixed point. In storytelling, we craft narratives around a pivot point. The hero’s journey is round and symmetrical. There’s a predictable dip into hell, a spark of revelation, and then the protagonist returns, forever changed. If you watch enough movies, rock bottom can start to seem like a romantic ideal.

But when you’re living the experience of changing a habit or behavior, it doesn’t feel so smooth. The journey is in the context, and we don’t know where we are until we can look back on where we’ve been.

For our friend, his coma became the pivot point because of the trajectory that followed. That point could have been any moment before or after.


From afar, change might look like this.

chart graph of recovery and rock bottom fixed

Up close, it might feel more like this.

chart graph of recovery and rock bottom fixed

A day, month, or year, can feel like a struggle, with no end in sight.


The day my partner quit smoking, he got two Italian beef sandwiches and a sausage at 5 in the morning and ate all three while watching the sun rise. Then he smoked three cigarettes and felt like death. That wasn’t the last time he gave in to the temptation of smoking or binge-eating, but it’s his narrative: the pattern he sees when he looks back on his hero’s journey.

Any point in time can be your turning point. And you can have as many as you need.

I haven’t experienced addiction and recovery firsthand like many of my friends, but I’ve been close enough to know it’s rarely a smooth trajectory. We all have own methods of avoiding pain, and, mountains or molehills, it’s a matter of continuing the upwards climb.


Breaking the Seal: Becoming a Pivot Professional

As a teenager, when drinking in its forbidden splendor was a habit to be worshipped, my girlfriends made a big deal over not “breaking the seal.” We were proud to be in the loop on any aspect of this adult culture and talked about it constantly. We would resist going to the bathroom until it was so urgent that we simply had to go. Then there would be much giggling about peeing in the most idiotic places around New York City. For the record the idea that by “breaking the seal” and emptying your bladder you will influence the frequency with which you need to urinate is not supported by science.

This idea might holds more water when applied to decision making and career pivots.

After I applied to a Masters in Counseling, I felt an embarrassed freedom, as though I had just realized that the prison I was stuck in had been unlocked the whole time. On the other side of that perceived barrier, approached the Pivot Problem entirely differently.


When I realize my barriers are make believe.

For years, I could not imagine doing anything different. Even though I wasn’t happy in my role, it was all I knew. I scrolled through job listings with apathetic distance. I couldn’t imagine being happy in any of those roles because I couldn’t imagine being in those roles at all.

After crossing the threshold and applying to a graduate program, I am able to fully imagine myself in the program. I can see myself, my lifestyle, my studies, my internships, and gut check my feelings during that fantasy. Having passed through the clouding anxiety, I can see the options before me and interact with them in a new and real way.

None of this is surprising, yet I didn’t see it before. I know that the biggest barriers are my own construction, but somehow I can’t feel it’s true until I experience it. Decisions, especially surrounding my career, are something I’ve let become a barrier, and I need to desensitize myself by jumping over that barrier more and more.

Desensitization, or exposure therapy, is the process of overcoming a phobia or anxiety by systematically interacting with or visualizing the thing that terrifies you. When you can understand that it won’t kill you, it actually does make you stronger!

snakes 1

This is fine. Totally fine.


I’m not dying. I’m not dying. Am I dying?

I am indecisive not because I am afraid of change, but because I’m afraid of choice. I’m uncomfortable with the threshold itself. With exposure, and evidence that it won’t kill me, I’m becoming more comfortable with the thing that I fear!

I saw a job posting today at an organization that I’ve admired, but have not been able to see myself in. With newfound clarity and power against my pivot paranoia, I started an application. I met a fellow altMBA alum today and her I was applying for this role. “You broke the seal,” she said, “and now you’re seeing options everywhere.”