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  • Writer's pictureFred


Clocking in with my third blog post from B-school - let's go.

Me (center) with a portion of Section F during our retreat in Sunapee, NH.

Getting more personal (or professional?)...

My first semester at HBS is over halfway done.

I have mixed feelings about my experience so far. There's a lot to go over in general, but I want to focus on my professional pursuits for the remainder of this post.

I'm sort of at a decision point. A weird one.

For the first time in my (adult) life, I'm uncertain of what the next step looks like.

The uncertainty isn't about the goal. I know I want to raise my own venture capital fund either by the time I graduate or at some point in the near future (within 2 years after graduation).

The uncertainty is in the how. How do I effectively use HBS to get there?

I can't remember facing such uncertainty as a professional. I've always had both the what and how to achieve my goals in mind. Makes life pretty straightforward, albeit boring.

Now, however, I know the what, but I don't know the how. Or at least, it's not immediately clear to me.

That unnerves me. Because I don't have a clear how, I feel like I'm not using my time wisely between my academic, social, and professional endeavors.

I don't know if the time I'm spending each day gets me closer to my goals.

Two of my classmates (on two separate occasions) asked me questions that I've been chewing on recently:

  • If you could do anything this summer, what would it be?

  • What are you really here (at HBS) for?

I've been spending a lot of time thinking of these two questions. I have answers to each question, but I'm afraid that they might be wrong.

  • First answer: If I could do anything this summer, I'd love to write full-time on my newsletter, Founder to Founder (F2F), (and create other forms of content) and travel to see founders I've written about over the years.

  • Second answer: I'm here at HBS to get the credential (the MBA) that gives me credibility when talking to potential limited partners (LPs) in raising a VC fund, and become a more "polished" version of myself in a business and social sense that will help with the former.

As much as these answers are genuine and true, I fear they may be wrong.

Maybe I should just settle for aiming for a regular full-time internship. Maybe I should abandon my goal of raising a fund given my non-traditional background (relative to nominal venture capitalists) and the high interest-rate environment that the U.S. economy finds itself in currently.

Let's say I give into my fear of being wrong and pick the safe options by following the above. While there's a clear path forward, I would always regret not taking the risk to achieve the goals I stated in answering my friends' questions.

The things that got me to HBS (primarily my charming personality *wink*, followed by my unique blend of being both an engineer and writer) might not be the things that get me to the next stage in life.

Do I continue following my curiosity with F2F? Or do I "grow up" and be realistic with my choices in front of me?

Between the "safe" and the "risky" options hides a third question:

What's more painful: failure or regret?

As much as failure sucks, regret is worse.

Regret's pain stings for much longer.

Regret sows the seeds for nostalgia, which leaves you fixated on the past and stuck in the present.

Regret takes your eyes off of the future.

You don't learn anything from regret. But you do learn something from failure.

I would rather fail than suffer regret, and I regret not working on F2F full-time before going to business school.

I don't have enough left in the gas tank to try again with F2F. Quite frankly, I'm exhausted. I have been writing non-stop for the past five years while working a full-time job in academia, aerospace, VC, and then product management, then just to jump into the most intense MBA program offered on the market.

I haven't had time to rest at all.

Ironically, I'm exhausted at a time where I am realizing I have only one more great shot at achieving my goal with F2F and the VC fund while being a student again. (I'm going to avoid getting into details of exactly how I will accomplish this here for the purposes of this blog post.)

I'm 10 years older than I was when I first came to Boston; things have changed.

I have changed.

If there is any time to grind, it's right now, but fuck, I'd be lying if I said I know that this will work out.

I don't. I have no idea. The uncertainty kills me.

But I have to try, even if I end up failing.

I'll regret it for the rest of my life if I don't. I'm going to trust in following my curiosity once more, despite the uncertainty.


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