Back when Jeremy and I first started dating, he took it upon himself to introduce me to what’s now one of my desert-island type shows, Mad Men. This was back in 2013, six seasons and therefore six DVD boxed sets in. I set a goal for myself: blaze through seasons one through six, so I could be properly caught up once season seven (parts one and two) dropped the following two years. (This isn’t an ode to Mad Men, although I should probably write that post too. Anyway.)
That first watch-through was a self-imposed race to the finish line. It’s since become a staple in my rewatch catalog, which is helpful, because it took a subsequent second, third, fourth, etc watch to really soak it all in. But there’s this scene in season four’s finale, “Tomorrowland” that’s stuck with me since that very first time through.
Our deeply flawed, tragic anti-hero Don Draper calls up his romantic interest Dr. Faye Miller, to break things off with her after proposing to another woman.
A short exchange ensues. The call ends quickly. But not before Faye delivers the final zinger:
I hope she knows you only like the beginnings of things.
I am no Don Draper.
Beginnings are my least favorite part of things.
I’ve always had a little twinge of melancholy vibrating underneath my consciousness. I’ve learned over time how to dial it up and down depending on how much it serves me, but it’s never not there.
I actually love this feeling most of the time — it’s part of what drives me, what keeps me connected to humanity, and what prevents me from missing the moment I’m in.
Sometimes, though, the melancholy goes into overdrive. Beginnings of things are both exciting and terrifying to me, meaning they’ve usually got a nice dose of that ever-present melancholy running through them. It’s not that I don’t like beginnings (I do), it’s just that when given the choice between ending-middles-beginnings, I’ll choose the former two almost every time.
I was often labeled a perfectionist when I was little, but really I was just a kid looking for love and acceptance like all of us are.
My issue was that I was dually invested: I was invested in the ideas I had, but I was also invested in people’s reactions to them.
And so often times, when I wanted something, I’d wait and wait and wait until the waiting reached an absolutely unbearable level, and THEN I’d finally go after what I wanted.
But at that point, I’d spend so long on the inner negotiation process of making sure my actions were palatable to both myself and others that by the time I finally did whatever it was that I was initially excited about, it had lost its luster.
Not only that, it had lost the fire I’ve now learned is essential to getting something off the ground and keeping it there.
It was — and still is — hard to let anyone see me stumble. But starting, of course, involves stumbling. They’re called baby steps for a reason: you wobble and you fall a lot, but eventually you take one step after the other and find your stride. The wobbles and falls are a necessary part of the process. What’s the quote? Every journey begins with a single step? Thankfully, I’m a journey-over-destination kinda gal — but unfortunately, I’m also a journey-over-starting-line one too.
As an extremely self-motivated person, you’d think I would’ve conquered this “beginnings-of-things” hurdle already. Nope. I still have a way harder time starting stuff than I wish I did.
The difference is that over the last decade or so, I’ve developed different tools and protocols to help keep my momentary fears from turning into melancholic overwhelm.
I have learned how to be brave enough to risk breaking my own heart.
If you too are the anti-Don Draper (hopefully in many ways…) and prefer middles over beginnings, I thought it might be helpful for me to share a few of what I do — and don’t do — to get myself over that starting line and deep in the process I love so much.
Here’s exactly what I don’t do, what I DO do, and the mindset tools I use to help me with both:

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