My 3 best investments of 2016

Damn, this year was a big one. It was my first full year of marriage, the first year that I had a six figure income, and the first year that we bought real estate in a different state.

Early last year, I wrote a particularly vulnerable post, in which I said: I’ve spent my life so far valuing financial security over connection and community, and it’s not making me happy. It’s time to change my life. 

This year has been all about that change. And man, it’s been tough.

One of the toughest parts has been getting up the courage to spend money on myself. Bold, uncomfortable purchases. Big purchases. Every one of the purchases below came with nights lying awake – am I worth it? Will people laugh? Am I going to regret this?  

Related reading: 3 best investments of 2015

My 3 best investments of 2016:

Winnie | $250 

I’m not even going to bother explaining myself, I’m just going to overwhelm you with cuteness:


For the same price as a pair of nice leather boots, I got a running buddy, co-worker, foot warmer, defender-against-squirrels, and occasional bed-wetter.

On a more serious note – I have wanted a dog my entire life. But as I got more and more into financial independence and remote working, I put that dream on the backburner. Medical bills, training, pet-sitting…dogs are freakin’ expensive. It didn’t make sense – logistically and financially.

As I get older, I find more and more the need for balance. Balancing my social life with my budget. Fun with frugality. My future with my present. Family expectations with personal values. Experiences with expenditures.

In this case, I re-balanced my life to include a little more fun and a little less frugality.

A coaching call with Penelope Trunk | $350 

Penelope Trunk is my hero. She’s honest, feminist and always pushing the envelope on tough topics like career, education, parenting, and marriage. And she’s a coach! Who charges $350 an hour…goes without saying, that’s a little out of my coaching budget (which before now, was $0).

So what changed? I was faced with a big career decision. I couldn’t make up my mind. I went back and forth for weeks. I drove Andrew crazy. I drove my friends crazy. I lost sleep night after night, lying awake, staring at the ceiling.  And then one day, bleary-eyed and jittery from too much caffeine and too little sleep, I went to Penelope Trunk’s website and clicked Buy.

A MacBook| $1199 

Remember that Penelope Trunk call?  It was fucking amazing. The day after we spoke, I quit my job to work for myself.

Which meant I needed a computer. The last time I owned a computer was in college, since I’ve always had jobs that provided a laptop. So I went and bought myself a macbook. It was the first time I’ve bought myself something that cost four digits, and my first big “I work for myself” purchase (can you say write off?!).

Here’s a picture of me eating lunch at my desk with my new computer and my only work friend:



Here’s to a calmer and clearer 2017. This year, I’m doing things a little differently. I’ve listened to my wonderful friend Stefanie about the power of investing back into your business. And I’ve taken inspiration from Carrie at Careful Cents, and given myself a “development” budget. If any money is leftover by 2018, it’ll get donated to charity. What’s on the list? FinCon, coaching, outsourcing, travel, and some advanced dog training. Because my little co-worker is driving me nuts!

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