Life Lessons Learned from Leading a Hackathon

A flashback from four months ago, when the business association I volunteered for brought up the idea of ​​hosting a hackathon in conjunction with their annual business forum, the “hackathon seed” was planted. Appointed to co-chair the hackathon segment with one of the 6-team strong central committee members, he had no idea what I was signing up for.

No one on the team had any experience running a hackathon; I was the only one who had participated in a couple of them and that’s it! All we knew was that it would be nice to host one. We challenged the conventional weekend hackathon model and settled for a week-long hybrid hackathon-case challenge. We had 6 case sponsors from various industries crystallize their operational problems into problem statements for participants to challenge. Boy oh boy, that was an amazing 4 months that I had! I probably never would have agreed knowing how devastating it was. But still, there are some lessons that I learned and wish to impart to you:

Life Lesson 1: Always take promises with a pinch of salt.

People can promise you this and that, but at the end of the day, they don’t own you anything. They are not required to do what they promised, nor are they allowed to enforce it. It all boils down to the fact that business is business, mutual benefit is mutual if he or she benefits more than you do. Unless it’s written in black and white, never take promises for granted. Always take things with a grain of salt and don’t hold a grudge if promises aren’t kept. This leads to my second life lesson: plan ahead of your planned plan.

Life Lesson 2: Plan ahead of your planned plan

Plan plan plan. Period. I can’t stress enough the importance of planning, because I have failed terribly by not planning a contingency plan. When things go wrong, it will multiply until you can grab it or have someone experienced enough to rescue you (Trust me, I’ve been there, I’ve done that).

Even if you’ve planned well enough to pass in the eyes of the experienced, Murphy’s Law (what goes wrong will go wrong) never fails to foil your plan. He always makes the effort to write Plan B, or even Plan C, as it can be his lifeline in case of radioactive fallout.

Life Lesson 3: Delegate, Delegate, Delegate

Organizing a hackathon is quite difficult. Opting to break out of the traditional hackathon model and do something new is even more difficult considering that every “How to Host a Hackathon” or “Hackathon 101” guide became a reference rather than a template. Additionally, our hackathon was split into “Student” and “Open Category,” which added another layer of complexity in an attempt to appeal to a broader audience. My unwillingness (or rather, inability) to delegate work led me to spend countless nights writing letters and emails, planning the program, and corresponding with sponsors.

So even if you feel guilty about delegating work or prefer to do it yourself because you THINK you can do a better job, make a conscious effort to delegate available tasks to your committee. They’re there for a reason, and delegating work will go a long way toward keeping you sane and well-rested.

Life lesson 4: Learn to fight alone

There will be times when you don’t get the help you expected (Going back to Lesson 1, don’t take promises for granted). There were times when I thought, “What am I doing all this for? Why did I trust him/her? Could I be doing something more meaningful?” While I was lucky enough to co-lead the hackathon with my mentor, he is not a superman or hackathon guru. You will definitely reach a point where he will be exhausted and you will feel helpless and hopeless. It is these moments that your actions define you. Press and make it count.

Life lesson 5: Be prepared to be disappointed again and again

Despite all the hard work you put in, things will never go as planned. Remember the inflexible Murphy’s Law? This is why you always plan ahead of your planned plan. Empty promises, backing out at the last minute, default; whatever, I’ve experienced it.

Aside from the disappointment in others, you will be disappointed in yourself. Zero experience is often my “Get Out of Jail Free” card for whatever mistakes I’ve made, but it’s by no means an excuse for everything. Over and over again I let myself down for not meeting the demands and executing what was expected. It is as if success is simply beginner’s luck. But trust me, your luck improves after a few rounds of failures.

“Let me tell you something you already know. The world isn’t all sunshine and rainbows. It’s a very mean and nasty place and I don’t care how tough you are, it will bring you to your knees and keep you there permanently if you let it. You, me or no one is going to hit as hard as life. But it’s not about how hard you hit. It’s about how hard you can take a hit and keep moving forward. How much you can take and keep moving forward. That’s how you win” -Rocky Balboa

Life lesson 6: Don’t strive for perfection. Instead, strive for integrity

When you have a seemingly endless list of things to do, never try to do things perfectly. Instead, aim to bookmark it and move on. I’m a self-proclaimed perfectionist, or even borderline OCD: I’d proofread my drafts a couple of times, send them to others, and proofread again. In the weeks leading up to the hackathon, when time is of the essence, such behavior is unwarranted.

Start with the end goal in mind and aim for practicality. Do a couple of checks, make sure what you’re doing is achieving what you set out to do, and move on; there is no point in staying alone to make it perfect.

Life lesson 7: Just do it

Don’t wait for things to happen, because everyone on the team is going to think the same way. Instead, take the initiative to just do it. This is human nature: no one wants to do dirty work when they have “better” things to do. Things won’t work on their own. If so, it’s because someone else did the hard work, not some fairy who waved a magic wand at him and things magically got done.

One thing to keep in mind is to be prepared to spend a lot of time learning new things. I spent countless hours looking for templates and writing letters to sponsors and participants. It was a steep learning curve learning how to integrate the various aspects of a hackathon (sponsors, food, venue, participants, logistics, etc.) and ensure that things fit together perfectly on the actual day.

Life Lesson 8: Know your WHY

Overall, the hackathon was a success despite all the hiccups along the way. At the end of the hackathon finals, when everyone was having so much fun celebrating, I saw their smiles and laughter. It took me a good couple of minutes to sign up and soak it all in, but that’s when it hit me: I found my WHY.

The hackathon was more than just an event for participants to compete against each other for cash prizes. It was an event that brought people from all walks of life together and had them plant an idea in someone. It was gathering friends who are often busy with their own things and having a fun time. It was seeing the smiles of everyone who had attended and gained something from this event. For me, it was seeing the seed of the hackathon grow and bear fruit; and I was lucky enough to have grown along with the hackathon to be a better organizer, a better friend, and best of all, a better individual.

Thank you to everyone who has made this event possible. #hackathon #noregressions