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Op-Ed: A Letter to Myself: Lessons From Three Years of Breaktime

Updated: Jun 5

About three years ago, as a freshman at Harvard University and just days after founding Breaktime with Connor, I wrote a letter to my future self at a school-sponsored event. I quickly forgot about it until it recently appeared in my mailbox. In the letter, I wrote:

“...I just started working on Breaktime to confront the challenge of young adult homelessness. I have no idea how it will turn out, but no matter what, I’m sure it will be one heck of a journey...”

To celebrate Breaktime turning 3 and reflect on the crazy journey up to this point, I decided to write a letter to my past self with some lessons and advice that I wish I had known from the start.


Dear Tony,

Surprise! This is Tony from the future here to report that both you and Breaktime made it to 2021. As you expected, it’s been one wild ride. While there’s still so much I have yet to learn, here are the three most important lessons so far that I wanted to share with you.

1) A Learning Orientation Is Powerful.

It’s okay to not know exactly what you’re doing. In fact, you’ll soon learn that nobody actually does and that you should be wary of people who claim that they do. However, you don’t have to be an expert to make an impact. You just have to be intentional and consistent about learning.

As you start Breaktime, being a student is both a blessing and a curse. On one hand, people will treat you like a child and assume Breaktime is a school project. On the other hand, this is exactly what makes being a student entrepreneur so meaningful. You will be surprised at how many non-profit organizations, experts, community members, and policymakers will agree to meet with you (just through cold emails!) because you are a student and in the ‘learning phase’ of your life.

The most valuable use of your time is to deeply understand the nuances of the problem you are addressing. Discovering the specific gap that you can fill is not only exhilarating, but it provides your work with direction and precision. It can feel like peeling an onion, layer by layer, until you reach the core. You entered Harvard curious to learn more about the causes and consequences of homelessness. To go one level deeper, you started volunteering at the Y2Y Harvard Square Shelter to address young adult homelessness, in particular. You will learn that there’s something special about the intersection between young adult homelessness and jobs because stable employment is the most critical factor in achieving stable employment. Indeed, at Y2Y, more shelter guests request support for help getting a job than for getting housing. Finally, after several more months of speaking with young adults and community organizations, you’ll discover that young adults experiencing homelessness often have a challenging time obtaining their first job to start out their career. It is the deep understanding about this specific challenge that will guide your work.

Albert Einstein is believed to have called "the power of compound interest the most powerful force in the universe." While typically used in financial contexts, the power of compounding can and should be applied to your own learning. There is immense power in taking consistent baby steps. Focus on making a 1% improvement each and every day in whatever you are doing because when 1% compounds each day, it doubles in just 72 days. Whether it’s learning just a bit more about a particular problem, having one productive meeting, or sending out a few emails, do something (even if it’s small) each and every day. “Don’t break the chain,” as Jerry Seinfeld put it. There is so much power in consistency and to keep yourself motivated, just think about how much of a difference baby steps will make in 72 days (or even 3 years!). Looking back, you will be shocked at your own learning and growth.

Build a team of learners: The critical trait you should look for in any hire is learning orientation. We don’t expect anyone on our team to be an expert (Connor and I sure were not when we started!), but we do expect everyone to have the curiosity and humility to cultivate new skills, deeply learn about problems, and initiate creative projects and experiments. When Plan A doesn’t work out (which is inevitable), you will want to surround yourself with people who are able and excited to learn, explore, and try new models.

2) ‘Plan A’ Rarely Succeeds. Figure Out Your North Star and Be Willing to Let Go of Everything Else.

I think you’ll be surprised to hear that Breaktime is no longer developing the Breaktime Cafe — yes, the project that was in development for two years and into which our team invested countless hours and resources. You’ll be even more surprised to hear that we were only weeks away from opening it when we decided to stop the project. We had a spaced secured, architectural plans and permits in hand, construction in progress, a General Manager nearly hired, and young adults who were preparing to work there. That was March 2020 and when the world surprised us with a global pandemic, we were forced to let go of Breaktime Cafe. And yet, Breaktime is still on track to launch the careers of 100 young adults experiencing homelessness this year. How did this happen?

Your very first plan rarely ever works out how you think it will. You have to maintain the cognitive dissonance of understanding this while also still working as if it is going to pan out how you intended. When insurmountable challenges do occur and you are forced to stop with Plan A, you may feel like you have failed. You may feel like pivoting to Plan B means that you’ve wasted the time you’ve spent working on Plan A. You may even feel that Plan B doesn’t even resemble what you initially set out to work on. These feelings are completely valid, but I want to share alternative perspectives:

First, a mentor once told me that the average successful startup pivots four times before hitting runaway impact and success. By this measurement, pivoting is natural. In fact, Breaktime may even have a few more pivots to go. Second, even when Plan A fails, the learning, relationships, and resources you’ve built are still incredibly valuable and can be leveraged to launch Plan B. Finally, remember that what you are working on is not one specific plan or model. Instead, you are working toward a larger mission that a specific plan or model serves. Understanding precisely what this mission is will help you survive and succeed during the pivots that will inevitably occur.

Early on, be intentional about discovering and defining your North Star. Your North Star is a stable, compelling, and ambitious mission. While it may evolve or become more refined over time, it should not completely change. Breaktime’s North Star is a commitment to ending young adult homelessness through purposeful transitional employment. When you remember that you’re working toward your North Star and not just opening a cafe, it will be easier to accept evolving plans.

When Breaktime stopped the Breaktime Cafe project, we took stock of the learnings, people, and resources we had and realized that there were numerous paths toward reaching this North Star. During the pandemic, many young adults experiencing homelessness were eager to work, there was a kitchen in our building, and there was a rapidly growing food insecurity crisis across Greater Boston. If we had been attached to opening our Cafe, we would have waited more than a year before it became a viable operation. Instead, we launched the Double Impact Initiative (in collaboration with numerous community organizations and the City of Boston) within two weeks to employ young adults experiencing homelessness to prepare and deliver nutritious meals to families in need. In 2020 alone, Breaktime hired 25 young adults who prepared and served over 500,000 meals. The Double Impact Initiative continues to evolve today as we now train young adults and connect them with community organizations and purposeful companies who have labor needs. The day we decided to release our attachment to the Cafe at the start of the pandemic was the day we began to open our eyes and hearts to the immense possibilities that exist to fulfill our mission. If there’s a silver lining to the tragic crisis of the past year, it is that Breaktime’s model has grown stronger, more impactful, and more scalable, empowering many more young adults than we would have with Plan A.

3) Always Put People First.

Despite all of the emails you send, spreadsheets you use, and calls you make, remember that at the end of the day, this work is always about people. As often as you can, get away from your desk and spend time talking with young adults, team members, and community partners. Maintaining proximity to people and the problem you are addressing will make you a more informed, empathetic, and effective leader. Putting people first not only means using people-first language (such as “people experiencing homelessness” instead of “homeless people”), but it also means elevating young adults experiencing homelessness to share their voice and help direct the organization. It means including them in program development meetings, fundraising pitches (there’s nothing more powerful than a young adult with lived experience of homelessness sharing their journey with a potential funder), and fun activities (like going to Red Sox games!).

Putting people first also means investing in building your team. Choosing who to work with is perhaps the most important decision you will make. Having a co-founder like Connor — who is passionate, trustworthy, and creative — has accelerated our work in every way. However, Breaktime won’t always be a two-person team and as you bring on new staff, remember the importance of learning orientation. Just as Breaktime continues to evolve and pivot, roles within the organization will inevitably shift as well. As a young organization, focus on bringing on passionate and adaptable ‘athletes’ who are comfortable playing multiple roles (instead of someone who only knows how to perform in one very specific role). Building your team will take a lot of time and energy, but it is worth it. The CEO of DoorDash (who incidentally shares a similar name: Tony Xu) spends more than 50% of his time on hiring and team development. Since where you spend your time and resources reflects your priorities, make sure that team-building receives the time and resources it deserves.

Finally, remember that it’s okay and often necessary to prioritize your own health and well-being. Don’t listen to the entrepreneurs who claim that the only way to be productive and impactful is to work around the clock. Remember that tackling a challenge as large as young adult homelessness will always be a marathon and not a sprint and taking care of yourself is exactly what is required to run a good marathon. When you wake up, in the middle of the day, and at night, ask yourself, “What can I do for myself right now to feel more comfortable?” We so often get caught up in meeting deadlines, attending to others’ needs, and checking in with team members that we completely forget to check in with ourselves. Taking care of yourself is worth it.

Now turn off your computer and get some sleep!



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Dec 19, 2023

A very cool article, you have written everything so clearly and coolly, you have provided information one hundred percent. As for studying, it is always a rather difficult topic, because it is given to everyone in different ways, and especially if you take a break. I remember how I had difficulties with my nurse homework, but it was good that I promptly asked for help and did not let the situation go. This way I saved myself nerves and time without going into too much detail. But I can say for sure that learning is still multifaceted, no matter how much time you spend on it. But it's still nice to always learn something new.

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