My Fine Alter Egos – Or – Reminders to Live in the Present

Those who have spent some time around the Plastiq offices have probably heard me refer to one of my favorite alter egos – “Past Dan” and “Future Dan“. It all started as a joke when a co-worker and I were digging through some old code, and I just couldn’t decipher why I’d written it that way.

Past Dan must have been out of his mind when he wrote this,” I mused. Laughs all around.1

Since then I’ve been increasingly using the monikers to refer to both decisions or actions that I made in the past (Past Dan) and things that I’ll have to deal with in the future (Future Dan).

Examples of usage include:

  • Hmm… we can leave that one for Future Dan to figure out.
  • Well, Past Dan clearly didn’t know what he was talking about.
  • Alright! Looks like Past Dan already covered that case in the documentation here.

Over time, I became aware of an additional psychological benefit that arose from referring to my past and present selves as separate individuals.

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A “Bill of Rights” for My New Reports

Starting a new job can be both exhilarating and nerve-racking. As a manager at Plastiq, I view it as one of my most important responsibilities to – with the help of our excellent talent team – onboard new reports in a manner that instills within them the context and confidence to do a good job, as well as set the tone and pace for our on-going working relationship.

To facilitate this onboarding, I thought it’d be valuable to compile a “Bill of Rights” that all my new reports can read, refer back to, and – most importantly – hold me accountable for during their tenure at Plastiq. It is my hope that these guidelines will provide a welcome centering influence as our work and roles continue to evolve over time.

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23 Rules for Living Without Regret

Easier said than done, but nothing worth doing is ever easy, right?

1) Don’t complain about anything you’re not willing to make an effort to change.  If you do choose to complain, then you have an obligation to do something about it.

2) Barring truly extenuating circumstances, do what you say you will, and do not do what you say you will not.  Let your word speak volumes because it is your bond.  If you are uncertain, remain explicitly uncertain to all relevant parties until such time as you can commit.  Be wary of others who may sully the reputation of your word – either intentionally so or not – by ascribing false or unqualified quotes to you.

3) Let every choice you make be an opportunity to discover and define yourself more deeply.  Make no unexamined turns, however unimportant they may seem.  Be deliberate.  Consider how your past and future selves will perceive your present words and actions.  Strive such that your choices transform into principles you want to have.  Actions form habits.

4) Endeavor to enter into all that you do without reservations nor expectations.  Don’t hold back, and don’t only do things because of what you hope to gain.  Respect the journey.  Live fully and expect nothing, and everything will feel like a blessing.

5) Accept the existence of your worst self.  Stare into a mirror until you cry.  I guarantee no matter how comfortable you are with yourself, this will happen if you stare long enough.  When you break, don’t look away.  Realize that you are exactly the way you are meant to be – perfectly imperfect.  It is alright to feel uncertain and to experience failure and to even hate yourself.

Recognize that you will not always be your worst self, nor can you always be your best self.

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Why You Shouldn’t Take that “Intro to CS” Course

Our scene opens on a charming coffee shop on the edge of the Boston commons.  It’s a crisp autumn day and I’m grabbing a midday pick-me-up with an aspiring entrepreneur friend, who has just informed me that she (or he) has enrolled in an intro to computer science course.

“Cool!” I’ll exclaim.  Then, with a raised brow, I’ll often inquire, “What are you hoping to get out of it?”

Invariably, my friend will patch together a response involving some combination of the following two reasons:

  1. I want to learn more about technology.
  2. I want to better manage or collaborate with engineers.

…I usually respond with a dejected sigh.  This is a scenario that I’ve experienced more times than I can count, and each time I’m two parts excited by my friend’s initiative and by the prospect of future CS-related banter, but one part concerned that my friend might not get what he (or she) wants out of the class.

The fact is, neither of the above responses are great reasons to enroll in an introductory computer science course (hereafter, “CS intro”), and here’s why…

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11 Tips for Productive Meetings

The following is a thought piece I wrote for the internal Plastiq wiki. I wanted to share it in case others may find it useful for their place of work. Please be in touch with any questions, comments, or suggestions! A document like this only gets better with iteration.

Meetings are useful for two reasons and two reasons only: information sharing and decision making.  A meeting should be called for one, the other, or both reasons.

Importantly, when I refer to “meetings”, I don’t mean ad hoc chats that may arise spontaneously around the office, although it’s important to be mindful of those too.  Rather, meetings in this context refer to a time and place reserved for a set list of attendees to gather together and accomplish a well-defined goal.  They can range from the informal (one-on-one catchups) to the formal (exec weeklys), and generally they would be well-served to follow some general guidelines.

So, without further ado, here are my 11 tips for productive meetings (in no particular order)…

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Creative Catch-22 (or) Why I’m Big in Japan

I always wondered about artists, and how their work must often be inspired by the people in their lives.  What joy and pride it must bring someone to know that a beautiful love poem was penned in their name!  And to an equal measure, what mixture of horror and sadness must accompany words about hate or betrayal.  I’ve written songs and poetry since I was in grade school, and my close friends often make fun of the fact that an overwhelming majority of my compositions are about happiness and love.  In truth, it’s because I’ve often struggled with allowing myself to publish negative emotions about people.

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