Calibration, growing pains, and saying “good morning”

October 20, 2019

I’m moving off of Tiny Letter, and sending the “hello, I wrote a new thing” email update through Revue now. So that’s new, and we’ll see how it goes. As always, feedback is welcomed with open arms. (Side note: I’ve recently noticed a trend where people give you feedback and preface it with something like “To be candid with you,” or “I’m saying this because it’s the right thing to do,” as if feedback is offensive. I hadn’t really internalized that it may be that a lot of people who say they want feedback actually just want positive feedback. It’s a bit odd to me, because I don’t think it warrants some praise to give someone feedback—positive or constructively—but perhaps I should start working on ways to seek out better feedback more proactively.)

Yes, it’s true: it’s almost one-third of the way into Q4 and I am just now prioritizing time to reflect on Q3. It was a bit crazy, that’s for sure. The last three months or so have been incredibly important for my personal development, and I am truly thankful for a number of key influential people in my life who have been showing up for me and asking me some hard questions lately. Ugh.


Between late July and early August, Possible Finance went from being a team of 20 to a team of 30. That’s a big change, and brought a distinctly different feeling. We moved into our new headquarters, and I got to have the pleasure of being one of the people who got to help fulfill the vision of the new space. Our new office is spacious for our current size, and being a true-to-spec startup, we’ve added a Room to increase the number of places we have to make phone calls (no more calls from the supply closet!).

In September, the Rosebud Scholarship Fund was awarded and got to announce $25k in funding from State Farm. We are so incredibly grateful for everyone who sacrificed time out of their days to help support us and we can’t wait to show everyone the next project that’s underway—stay tuned!


Calibration, the act of minimizing measurement uncertainty, is one of those things that is hard to gain without living through things. In startup terms, calibration as I understand it, is what allows someone to make an appropriate decision for that specific situation based on information from similar and/or relative scenarios. For example, being able to make a hypothesis about when we should hire a Head of Something New based on when a previous company they worked at hired a Head of Something New and how it went. Lately, I’ve been feeling my lack of that more than ever before, both related to things at work and within other areas of my life. It’s kind of frustrating because it seems like one should be able to find pseudo-calibration through, say, vicariously collecting life experience, right? Yet as much as I aim to do that, the main problem with vicarious experience remains: the main variable is missing, and that variable is me.

In practice, lack of calibration looks like me frequently asking myself, “Are we being overdramatic about this?” to which the answer is usually yes, but at the same time, sometimes certain feelings in certain situations are echoed by others, which occasionally turns my sense of calibration on its head. If anything, I’ve recently realized and appreciated how much and how frequently I feel things. The main takeaway from this quarter is that it feels like my calibration is most lacking when it comes to figuring out how much patience is necessary. A lot of things in my life are products of me being somewhat impatient so it’s hard to see objectively just how much patience may affect different things. Patience is also probably the most difficult thing to seek calibration for because you literally cannot do anything but wait. And so we wait. We learn. We continue to get up each day and see that although a month or year may not be complete, a day is completed one second at a time.

Growing Pains

For the sake of brevity, I don’t feel like I need to say much more than having 10 new team members in the span of two weeks was a lot. Changing our culture and composition, our newest additions rounded out our team nicely and gave us many new people to cheer for and with. Some of the things that I love most about working with other people were multiplied, and I have more people to learn about, learn from, and laugh with. At the same time, I’m recognizing new things that come with the territory—things that help everyone be on the same page—and I’m not always sure that I am a fan. I’m under no impression that anyone is always a fan of everything that comes with a growing team, but it definitely feels like having 20-35 team members is an awkward middle stage for company size: there aren’t enough people to have consistently dedicated structures and teams, but there aren’t few enough for everyone to operate as a single team all the time. We’ll see how it shakes out, and I’m keeping my ears open and eyes wide as I strengthen my calibration for process and structure.

Saying “good morning”

I recently had help framing by seeing things as expending energy inward and expending energy outward. I think this quarter has been a lot of expending energy inward as I try to work through a lot of things I’ve been thinking about, and being unwilling to see that I was relatively unhappy with things—or at least, less fulfilled and energetic about things than I usually am. I’d like to think that I do a good job of hiding that, but as I’d imagine is the case with most people, I’m not as good as I think. Some of my coworkers have noticed, saying that I’ve been quieter than usual lately (which, as we all know, is not really the first word most people would think of to describe me, haha). It’s as if, in the face of brief tumult, I’ve gone inward and reflected, rather than trying to boldly terraform new territory.

I’ve been lucky enough to adopt a lot of things related to culture at work, and while I love saying “good morning” to all of our team members, it can take a bit more for me to remember to treat that moment just as importantly as any other. “Good mornings” become habits which become relationships with people who are just as excited to work together to solve a problem with me, and I don’t wish to take that for granted. (Even when I am up in my own head about the world.)

Prepared for everything; prepared for nothing

Some of the hardest questions I’ve been asking myself lately are related to the future. Derek Sivers’ “How to thrive in an unknowable future” was some of the first material that I found that resonated with me and stuck, and second would be the Naval Ravikant episode of The Knowledge Project podcast. I totally get that I know things but I totally don’t know know things until I have the experience (see: above, lol). Therefore, the future, must like my aforementioned missing patience, is interesting because it’s the product of a missing calibration: how patient should I be about X? So, okay, I know that this is a problem that is never going away, and a lot of people have jobs doing exactly this as it relates to industry, but it’s certainly been at my forefront lately. I’m acutely aware of how comforting security and comfort are, and also painfully aware of how quickly I become bored by things that I’m sure about. And after all that, without certainty for everything that I cannot control in the world, by preparing for everything, I feel quite prepared for nothing at all.

Supporting Materials

Celestial Seasonings’ Bengal Spice Tea. I grew up drinking this and it certainly tastes like cozy autumn days. I enjoyed it iced and warm this quarter, and you already know I’ll drink it into the new year.

I haven’t had many new, noteworthy things lately, but I’d like to give a shout-out to plants. Plants are very cool (lol) and my mom gave me a new one that I have managed to keep alive so far!

Looking Ahead

There’s a small part of me that feels like Q4 will be invigorating, not because I am now reflecting on how Q3 went, but because I’m injecting intentionality into other facets of my life, and in a lot of ways, picking up speed. I’m personally excited for a lot of areas for growth, and feeling better about a lot of things. For the most part, my response to a rocky Q3 has been to pare down the number of ways that I have been spending my time, and lean into the most important ones. I can’t help but feel a little out of breath, but at least with a renewed sense of direction that’s totally directionless.