5-Months of Business Experiments: What I Learned about Myself, Business, and Relationships.


To the casual observer, nothing has changed in my life.

Here I am, back at the same seat that I’ve been occupying in my coworking space for the past four years; gearing up to bring another Model UN team to Budapest in November, as I have the past three years; working on new websites for my education companies, like I’ve done twice over the past four years; following practically the same routine that drove me to want to blow everything up and start anew.

Appearances can be deceiving.


My students like to ask about my motivations for instructions all the time, and frankly, I welcome it. If you can’t justify instruction, you shouldn’t give it.

That doesn’t mean that I won’t respond by simply stating, “Everything I’m telling you to do has a purpose. Just wait and see.”

Most of the time that’s true. Some of the time, I’m hoping it’ll work out. And then other times, I’m hoping nothing goes catastrophically wrong.

The most important mental change that I’ve made has been to stop working for my businesses. I realized that my days were consumed by putting out fires, answering piles of emails, booking hotel rooms and plane tickets, and not much else.

The thought of executing longer-range, strategic projects exhausted me before I could begin to work on them. I was working hard, but being terribly dumb about it.

Since returning from my summer adventures inChina and India, I find myself more focused on building my brands, planning two moves ahead of where I am. Making the decision to bring on employees and starting customer evangelist programs has freed me up to make bigger picture decisions.

The second big working style change has come in the way that I’m tackling longer range or more complicated projects. Before the summer, my goal would be to complete a project in its entirety and try to refine through iteration. While I’m not abandoning iterating, I’m working on completing smaller chunks. For example, I’m building the new Global Startup Challenge — which is what the Young Entrepreneur Challenge has evolved into — website in very small parts rather than rush through the entire site in a day. Today, I spent two hours working on the design and functionality of an email for more information box. The key here has been to work consistently so all of your pieces fit together in the end.


For about four months, I was working on onboarding my first full time hire for the All-American Model UN Programs. It was a stressful experience — trying to find the right person, coming up with training materials and a transition plan, and allocating funds to pay a salary; yikes.

Still, I decided it was time to pull the trigger. Then came the bad news. My new hire could no longer accept the position at the last possible moment.

A few months ago, this news would have devastated me. So much mental energy went into this process and then a door gets slammed on my face? Forget it, that would have sent me into a tailspin.

I have a better appreciation for sunk costs now. There’s nothing I can do to get back spent energy or time, all I can do is recalculate.

I moved forward with our beautiful new website launch, began to carry out the plan I had put together, and started looking for a new Program Manager to take over. Oh, and I started an awesome Alumni Associate program, and I’m super excited to start working with them!


“What a long day.”

“It was a long week. I need a drink.”

“Tomorrow is going to last forever.”

Let’s face it, life is longer than we want to admit. Sure, you have to appreciate the melodrama of exclaiming how short life is when you’re sitting on a Caribbean beach on a five-day vacation. But do you really want to work over 250 long days a year for five short ones?

That point I’m trying to make here isn’t groundbreaking: do something to enjoy every day. Here are some the ways that I’ve gone about trying to do so.

Don’t Let Your Schedule Dictate 
My daily routine makes me productive, it keeps me in rhythm, and it can drive me into the ground.

Do you remember when you were in high school and there were those days you had to leave early for a doctor’s appointment or some other reason? Did you ever think to yourself, “wow, I forgot the world’s still going on when I’m in school?” I started feeling that way when I would leave the office for moments.

I don’t like feeling trapped at my desk, so I’m trying to vary my schedule. Work from home one day. Take a half day off to take care of personal errands. Work from the public library. Schedule meetings offsite. Anything to get me out in the world.

Don’t Live to Work, Don’t Work to Live, Just Live
A year ago, I had no hesitation announcing that I lived to work. My work was my driving force. My schedule, my time off, my online social presence, my speech, almost every aspect of my life reflected that philosophy.

When I decided to shut down and start over, that all changed. I started living the way I wanted to, and not out of fear that something that I did could ruin my business.

At the same time, I’m conscious not to resent my work so that I can live outside of it. The balancing act is difficult, and each person has to make personal choices on how to keep it.


Some days are just going to suck. And sometimes those days are going to stack up, one after another.

For all the pieces out there about entrepreneurial grit, persistence, and resilience, few people address the pure emotional aspect of being in business for yourself.

Being a solo founder complicates the stranglehold emotional tie-ups can have. That’s been my experience, at least.

You wake up and check your phone to find 10 new emails, mostly junk. One is from a client and you read the preview, “unfortunately, I’m going to have to…” Great, it’s already starting. First thing in the morning and someone just backed out of a sale. Ok, whatever, deal with it. You eat a quick breakfast, cup of coffee, shower, and as you’re about to head to the office, you’re reminded rent is due. And utilities. And you remember that stack on credit card bills and student loan bills sitting on the table. ‘This happens every month,’ you remind yourself. You’ll get through it. Get to the office, respond to the client who just canceled on you, and you shiver thinking about what happens if you lose another one or two. You start emailing everyone else to make sure you’re on the same page and try to stave off another cancellation. Another email ding on your phone, you read the subject: ‘Alert: Changes to Your Flight Schedule.’ Damn it, now what? Your upcoming flight is being reschedule an hour later, which will make you miss your connection. Deal with it later, go check your mailbox. Run across the street to the Post Office, there should be $10,000 in checks waiting after the weekend. Insert the key, turn the knob, three envelopes. One from Office Max — promotion, one from American Express, — credit card offer, and one from the Post Office — your PO box payment is due. Just work through the rest of the day and try avoid getting too dejected; you’ll sleep it off and try again tomorrow.

Only falling to sleep is hard and waking up seems to be getting harder, too. This is where I was in my life in March.

The way I manage days like this has had a monumental impact on my life. It may even seem simple. I allow myself to feel sad. Or lonely. Or rejected. I’ve stopped wrestling myself and accepted these emotions as part of life.

So much of what I read treats this as weakness. “Get over it.” “You’ll make it through it.” “Find a solution.” Reading between the lines tells me to be stronger, as if it’s a matter of strength of will and nothing else.

As much as you may need to tell yourself, “I’m invincible,” you also need to realize that some days you’re just going to feel like shit, and that’s ok.


The best way to counter loneliness? Uh, stop being a lone?

I have some great friends. The ones you can call at 3.30AM with an emergency type friends.

I also value the relationships I have with some former students, seesawing from academic mentorship to life advice to friendship. These relationships mean so much more to me than I think they realize.

And yes, I’m even putting more effort and time into dating — which can be as miserable as it can be exhilarating.

But I also have people in my life that I want to be more connected to, but it doesn’t seem they want to be. I pinpoint these relationships as being the cause of my loneliness, not, as I questioned above, being alone.

This is the one chapter in this piece that doesn’t have a tidy bow as a conclusion. I grapple with whether I should let these people go, or if I should try to maintain relationships, or if I should redefine what relationship I have with them.

The conclusion that I have drawn is that one-way is unsustainable.


Every trip that I make with students, I have no choice but to overcome three bumps. These bumps aren’t planned and there’s no telling when they’ll make themselves known. Some bumps are easy to navigate because you have the experience — like taking a girl to an emergency room in India at midnight, five hours before your scheduled flight departure (true story). Some bumps are frustrating but have roadmaps — like forgetting a piece of your luggage on the MBTA while herding 12 high school students into the airport (also, true story). And some seem like they’re going to stop you dead in your tracks — like having the lovely woman behind the flight desk tell you that one of your students cannot board the plane because she doesn’t have the proper visa (yup, can’t make this up).

When I reflect on the past four years of wild experience, I find myself smiling and laughing the most at my horror stories. Really, I laugh at the faces people make when I tell them.

Two trips to the emergency room. Surviving laryngitis for a week while teaching. Navigating the streets of Budapest a week after the Paris attacks. No shows and cancellations. “What if my son wants to get off the plane after an hour [flying from Boston from Beijing]?” No visa, same day one-way direct ticket from Boston to Beijing (It costs just over $2,000 if you’re wondering). Threatened lawsuits. Former clients not submitting their payments. Former students cancelling contracts. A former student who started a competing business.

Oh man, what a ride. Every bump has been different, but none have stopped me yet.

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PS- If you’re looking for an update on what the heck I’m actually working on now, you know, for my living, I’ll be posting about that next! Make sure to follow me to get notified when I publish it.