Enjoy the habit

Does the person who rises several times a week at 5 a.m. to run for an hour, even if it’s raining or snowing, actually enjoy doing it?

Maybe some particularly good runners do (I’ve run thousands of miles in my life and I’ve personally never experienced the mythical runner’s high). But I think what they’re really enjoying is the habit.

Most of those runners would admit that, sure, it would feel a lot better to stay in that cozy bed than it does to stumble out of it, don their running gear, and head out the door into the cold early morning. But they’ve made it a habit. And the habit is where the enjoyment lies.

They enjoy the feeling of accomplishment. They enjoy the freedom throughout the day of knowing that they’ve already gotten their workout in. They enjoy the pride that comes with knowing they made a healthy choice, once again, and resisted the lure of the snooze button.

There are a lot of things they enjoy more than the run itself. But they’ve trained themselves to enjoy the habit.

Most healthy, positive, productive habits start as choices. We can make the choice to care more about understanding someone else’s point of view than we do about proving that we’re right. We can make the choice to be the kind of person who shows up early and can always be counted on to come through. We can make the choice to do a little more than was asked of us, or to be generous, kind, thoughtful, forgiving, etc.

Students, you may be spending a significant portion of your high school days doing things that aren’t your choice. But if you don’t enjoy them, maybe you could decide how you’d behave differently if you did enjoy them. And then make the choice to behave differently. Do it over and over again and it’s likely to become a (good) habit.

You may not enjoy everything you’re doing. But you just might enjoy the feeling that comes with making a good habit out of it.

Which kind of hustle?

I started Collegewise by myself in 1999 and went from zero to over 100 students in less than 18 months. When asked, I’ve often said that I was simply willing to hustle more than my local competition was. They had businesses. They had years and years of experience. They had the history and the reputation in the community that comes with it. They didn’t need to hustle. But I was starting from scratch. Hustle was all I had.

But there are two kinds of hustle, and it’s important to choose carefully.

The first kind is for people who believe that the end justifies the means. In independent college counseling, these hustlers spam potential customers, over and over again. They press their current clients for referrals. They’ll inject fear into their marketing messaging, disparage high school counselors, and generally do just about anything to benefit their business in the short term, even if it shrinks their trust and credibility in the long term.

But the other kind of hustle plays the long game. This is the independent counselor who’s always looking for ways to delight their current customers, not just to entice new ones. They’ll create a helpful resource and give it away for free to as many people as possible. They care more about pleasing the organizer and the audience at a presentation than they do about wedging their sales pitch at every turn. They follow industry news and attend conferences because it makes them more informed and aware.

Their version of hustling is doing those seemingly little things that might have little or no impact today, but collectively make an enormous impact tomorrow. That’s what makes the little things so hard to do, and why it takes hustle to do them.

Students, parents, counselors, and everyone else have the opportunity to inject a little hustle into their important work. It’s an advantage available to everyone. But you can’t just make the choice to hustle. You’ve also got to choose which kind.


In my life before Collegewise, I worked for a test preparation company that, while preparing students for standardized tests, was also an outspoken critic of the exams. As the CEO used to say, “We judge a test by the behavior it inspires.” I’ve never met a student who was more intelligent, curious, kind, thoughtful, or interesting just as a result of preparing for and taking the SAT. But I’ve met plenty who were spending far too much time, energy, money and mental energy, often at the expense of their happiness and available free time. The SAT is a bad test because the behavior it inspires is not particularly inspiring.

You can also evaluate the behavior inspired by just about any kind of scorekeeping.

For example, I’ve noticed that some students do an awful lot of keeping score during the high school years. Ask them what they’ve been up to, or what their favorite class is, or what they’re most proud of, and the answer will involve a comparison to another student.

Not just what grade they earned, but how their performance stacked up against the rest of the class. Not just the pride in their accomplishment, but why the comparison to the competition makes the goal so notable. “Compared to what or whom?” is always implied.

If scorekeeping helps you do your best work, great. Some people are motivated by the framing of comparison. But for most of us, the constant measurement against others only begets more measurement, not better work or better feelings.

There’s plenty of scorekeeping and measurement imposed on high school students these days without adding more of it into your life. If the scores you’re keeping aren’t inspiring behaviors that bring out the best in you, maybe it’s time to consider a different measure?

What can you do without asking?

If you decided to surprise your family tomorrow morning by cooking breakfast, my guess is that you wouldn’t need to ask for permission first. Even if you burn the toast beyond recognition, it’s hard to get angry with someone for doing something so nice. The thought and the resulting generous action are what count.

If you’re looking for more responsibility, more credit, more ways to stand out, etc., look at the ways you’re spending your time and ask, “What could I do without asking?” Not a selfish act that only benefits you, but a generous one that benefits everyone involved.

There’s no long line of competition to beat, no selection process, no need to get picked for this kind of contribution. All you have to do is see a need or opportunity and then show up.

Your summer class, your part-time job, your martial arts class, your workout with the cross country team–if you make a habit of trying to give more, chances are you’ll start getting a lot more back in return.

Sometimes the best opportunities are those things you can do without asking.

Beginning anew

One of the best things about New Year’s Day is the feeling of renewal. It’s a fresh start, a year full of possibility, a chance to press the reset button and really do things right. Let the New Year’s Resolutions begin.

A new school year is a similar opportunity, for both students and parents.

The school year has a definitive beginning and end. It begins with a transition and ends with another one, a nine-month cycle with a beginning, much like the start of the calendar year, that is the perfect opportunity to start anew.

Nine months from now, what would you like to be able to say about this school year? What would make you feel happy, proud, successful, etc.?

Parents, same question. In your role as the parent of a teenager who also plans to attend college, what would you like to be able to say about the way you played that role this year? What would make you feel proud? But careful not to choose a goal that’s tied to your student’s achievement. “Help my teen improve her grades this year” is about your student. “Focus more on my daughter’s effort than I do on the outcomes” is a goal about you.

No school year ever goes perfectly for everyone involved. But you can make conscious choices to do more of what worked for you last year, and less of what did not.

The beginning of a new school year is the perfect time to begin anew.


Zingerman’s Deli is one of my favorite businesses, and yet I’ve never tasted one of their sandwiches. They’re highly profitable, with their community of businesses earning over $13 million in annual revenues. They’re consistently innovating, always looking for new ways to get better. They boast a fantastic culture with employees who care. They even write, speak, and teach prolifically to anyone who’s interested, including their competition. But none of it happens by accident. Everything is intentional.

Take their recent blog post, “How to give great customer service over the phone.” Plenty of businesses give lip service to customer service, expressing it via a banner that hangs on the wall. But Zingerman’s takes the time to envision what great service might look like. They codify, teach, and measure it. And they inculcate it into everything they do.

Can you imagine the pleasant service surprise for customers who call them? What message does that attention and care on the phone send about the food and service on the premises?

You don’t have to work in a deli, or speak with customers on the phone, to learn from Zingerman’s example.

Most people reading this are involved in things they care about. Family, work, a project, a team, an organization, an event, etc. Do you have a vision for what it could be? Have you thought about how you might bring that vision to fruition? And most importantly, are you laying the tracks, day by day—and doing so with intention—to get there?

Your vision paints a compelling destination. But you’ll need some intentionality to get where you’re hoping to go.

Investment initiative

I graduated with some impressive business experience considering I was a 22-year-old who’d yet to work a real full-time job.

In my four years of college, I’d recruited, interviewed, hired, managed, and on one occasion had to fire, employees. I’d drawn up marketing plans. I’d talked down angry customers. I’d written advertising copy, pitched ideas, created training programs, planned events, worked in teams, bounced back from failures, and done lots and lots of selling.

And yet, as an English and history major, I never took a single course related to business. I never had an off-campus internship, either. I just availed myself of the opportunities around me.

I volunteered as part of the staff for new student orientation and was hired to run the program during my senior year. I ran discussion groups as the TA for a course. I worked as a security guard at the library and as a conference planning assistant in the dorms one summer. And I ran a spectacularly unsuccessful new-member rush for my fraternity (it was the first time I learned that “This is how we’ve always done it” is not a compelling reason to do something).

I was nowhere near the most successful or involved person in my peer group, much less in the entire student community. My comparatively short list of involvements wasn’t particularly noteworthy. Some were even pedestrian. But baked into them were countless opportunities to lean in, to try new things, to take responsibility, and to fail. And best of all, they were available to any student on campus regardless of their area of interest.

As college costs and the associated student debt continue to rise, families are smartly starting to look more critically at the outcomes of college when compared to the cost. Investments are made based on the likelihood of a return, and it doesn’t make sense to pay that much for college only to cross your fingers and hope for the best after graduation.

But with some notable exceptions of programs built to combine applicable skills with job placement, it’s difficult for most colleges to promise (and to substantiate) an outcome at graduation, career-related or otherwise. A college can only present the opportunities, but the student is the x-factor.

It’s the student who gets to make the choice. You can view the boundless clubs, organizations, jobs, and other opportunities as a limited-time offer, one you must take advantage of before they disappear. Or you can view them as optional add-ons if and when the desire strikes.

The opportunities are there at every college, famous and otherwise. But you have to invest the initiative in pursuit of a successful return.

Supporter or boss?

This upcoming online session, “Homework and the Self-driven Child,” makes a compelling promise for parents:

“In this class, we’ll explore the importance of helping children develop a sense of agency and responsibility so that your role becomes a consultant and supporter, rather than a boss.”

I don’t have any affiliation with the class, but I have enjoyed the work of one of the instructors, William Stixrud (you can find past posts I’ve written about his work here, here, and here).

If you’re experiencing those challenges in your house and the course’s promises are compelling, it’s $37 and runs on August 22. All the information is here.

Is your story working?

Students, as you progress through high school, what stories are you telling yourself? This question is not the same as “What’s happened in your life in high school?” What actually happens is not always the same as the stories we tell ourselves.

If your coach decides to start the new transfer student in the spot that used to be yours, what story do you tell yourself?

One possible story is that it’s a miscarriage of justice, a tale of an opportunistic student who swooped in and stole—and a coach who heartlessly gave away—what was rightfully yours.

But you could also view that circumstance as one that’s actually good news. An unexpected source of talent just magically showed up. Sure, you’re disappointed not to start. But what a benefit to your team. What a boost to your chances of winning the league title you are hoping to claim. What an opportunity for you to play a different role as a supporter from the bench, to push yourself even harder in practice, to make you and other players better as you rise up to match the new position competition.

It’s one event, but two very different stories. And the one you decide to tell yourself makes all the difference.

I’m not suggesting that students or anyone else should ignore the realities of the world, especially the unpleasant ones. But there’s a difference between confronting brutal facts and creating demotivating stories.

Is it the situation, or the story you’re telling yourself about it, that’s not working?

Be the different one

I’ve never been a Star Trek fan. But I heard an interview yesterday morning that included an anecdote about Leonard Nimoy’s character, Mr. Spock, that resonated with me.

During one of the early episodes, the script called for seemingly every crewmember on the Starship Enterprise to panic about impending danger. But the director pulled Nimoy aside and told him, “Be the different one.”

So when every other character was losing their cool, Spock calmly reacted with just one simple word: “Fascinating.”

It became not only a recurring line, but also a central theme of his character.

Lots of families fixate on the colleges most likely to say no.
Lots of parents take over the process for their student.
Lots of students over-schedule themselves to the point of exhaustion.
Lots of families view the college admissions process like an anxious rite of passage.
Lots of parents turn their kids’ journey to college into a status competition.
Lots of students care more about getting the A than they do about learning.
Lots of families turn every conversation into one about getting into college.

Lots, lots, lots…

What would happen if you made the choice to be the different one?