Planning is Everything, but the Plan isn’t

The importance of being prepared because the plan will inevitably fall apart.

The theme of preparation stuck in my mind immediately after the trip. The willingness to make sacrifices now for future success. On both an individual level and organizational level, due diligence is everything towards making smarter decisions. But at the end of the day, nothing is as predictable as you would like it to. Hindsight can be 20/20, but foresight is always a shot in the dark. Therefore, you can and should prepare all you can afford; but, without mental preparation of the plan failing, you will truly lose. Through some of my favorite quotes of the trip, I will explore the factors and vectors of working around inevitable struggles.

First on a tangible level, our own personal preparation is something we must consider. On the very first night, Peter Bell said “your track record has already begun.” With internships in the near-future it seems obvious, but the decisions we make now will be key insights for a future employer. What we do now will be scrutinized with great care in just a few short years. At its core, this leads us to ask ourselves the question: “How do I want to be perceived?” It takes a level of self-awareness that we are not traditionally taught in business classes. Luckily for us, Boston College is an environment conducive towards personal reflection.

In another realm, social media is an obvious example of curating our own perception. It has become over-said to have clean profiles that avoid negative reactions. Don’t post anything stupid, seems too obvious. On the other side of that, how can you curate a LinkedIn profile that is not just avoiding failure, but building for success? I don’t think we have been advised and encouraged enough to think: “How can I put my own personality into this profile? How can an employer interpret my personality through a LinkedIn page?” Subtle questions that deserve consideration. I long for the day when your profile photo can be your favorite classic vine.

Pattern-matching is the quickest way to becoming mediocre.

Pat Grady on finding the right strategies

In thinking how to go about discerning your own path, a quote from Pat Grady struck me: “Pattern-matching is the quickest way to become a mediocre venture capitalist.” Applied to individuals, I find two possible interpretations. First, doing the same things over and over. The popular definition of insanity is to do the same thing over and over expecting the same results. It seems obvious; but falling into routines can be a real danger. Without changing up what you do, your thinking will not change either. A sort of ‘mental-loop’ can weigh down your growth and mitigate a unique personality.

Anything you do continuously you must ask yourself: is this a deliberate choice or just momentum?

Sophie Miller on knowing when to leave a position.

The second interpretation can be summated by a quote from Sophie Miller: “Anything you do continuously you must ask yourself: is this a deliberate choice or just momentum?” Especially in CSOM, many students follow a structure path because it is simply what is done before them. Having that finance concentration isn’t a bad thing if you consciously decide it is what you want. But sticking with it even when you are unsure of why you’re doing it is the real danger. It’s living on autopilot and only leads to a cookie-cutter existence. Again, this comes back to self-awareness and asking yourself difficult questions. In many ways, this trip made me realize the importance of the core curriculum and how important that philosophy class really is.

Professor Kane was not joking when he said we’d hear ‘pivot’ everywhere on the trip. It was so widely used it’s basically a cliché now. Because of that, I think it is important to break it down and redefine what it means for a company to ‘pivot.’ To me, it comes down to a slight grey area between hindsight and foresight; what have we been doing, and where are we going? The strongest (not just biggest) companies we saw were constantly evaluating themselves; Wonolo comes to mind. Their quarterly program of business employees completing jobs and writing a report shows their commitment to understanding their product. They interacted with their platform as users; this is foundational to informing good decisions. Not only does it evaluate what is working, but it gives companies greater insight how potential changes will affect users downstream. Practices like these are what makes good companies stay alive. Because given the pace of Silicon Valley as we saw it, being good simply isn’t enough.

The biggest obstacle is that there is no textbook for building Wonolo, no one has ever done it before.

Yong Kim on the struggles on founding a startup.

Staying ahead takes a certain level of scrappiness. It takes leaders and employees who are insatiable. One of my favorite quotes was from Brad Klune at Instawork: “I don’t believe in analysis paralysis… I want to make a quality product I believe in and get it out the door.” One of the tenets of ‘entrepreneurial spirit’ is the bias towards action; an unwillingness to wait at the hand of bureaucracy. If there might be an opportunity, take it. And this is really done out of necessity, startups do not have time to wait or be hesitant. There is a gravity to every decision that requires consideration and intention. Just like with personal decision, organizations must evaluate themselves to discern where they want to go, and how they want to get there.

The key balance is to find the right actions that are both intelligent and timely. Pivoting comes down to having a strong self-awareness of what is/isn’t working and how it could be improved. It’s a line between hindsight and foresight, genius and crazy.

Lastly, I’d just like to say this was my favorite class at BC and I could not be more thankful for the Shea Center and the amazing team that helped us through it all. Tech Trek did in fact change my life.

6 thoughts on “Planning is Everything, but the Plan isn’t

  1. I really liked this post Mike! I especially liked the quotes from Pat Grady, Sophie Miller, and Yong Kim you incorporated, I thought it really brought a personalized touch to the reflection!

    Liked by 1 person

  2. Great post Mike, as Kerry mentioned the quotes were a cool frame of viewing trip. I also loved Bell’s quote about track record–definitely a moment I’ve been thinking about since we got back to BC. Also great rooming with ya.

    Liked by 1 person

  3. Nice post Mike! My favorite quote was Sophie Miller’s and that we need to costly be evaluating our decisions instead of just blindly doing them just because that is our routine. That is something I am going to try and reflect on the decisions I make moving forward!

    Liked by 1 person

  4. Great post! There were so many good quotable moments during the trip. I am glad you had the thought of writing them down and keeping them for posterity. It was great getting spending time and getting to know you better.

    Liked by 1 person

  5. Hey Mike. It’s been great getting to know you during this class and on the trip. After reading these quotes you talked about, I really wish I wrote more quotes in my own notes. They really tell a great narrative and story about what we learned during our trip. Really loved your point about deliberate choices as I’ve found myself thinking about that a lot since the trip.

    Liked by 1 person

  6. What an insightful post and it was so cool to read about a very different perspective on this trip! I would definitely agree with that I had a whole new level of understanding for planning after this trip: it’s almost never going to work out perfectly, but not having a plan will be disastrous. Also, it was really nice getting to know you better during the trip and only realized after that we’re both taking Huang’s class haha.

    Liked by 1 person

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