2016 Kicked My Ass in Life and Business (+But At Least I Lived to Tell It)

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I'm trying to organize my thoughts into something meaningful and coherent, as this is really my very first deep, emotional blog post that I've written for Financial Best Life since we re-branded. Notice I said the word trying, because really all I can think about is how much 2016 totally kicked my ass.

At least I'm not alone. Even the New York Times considers 2016 to be one of the worst years ever. 

For me, personally, even amid an unnecessary amount of darkness, there were lessons about life, money, and business around every corner. In fact, in terms of personal growth, 2016 was one of my most successful yet.

But let's be clear about one thing – I'm not sad to see the b*tch out.

The 5 Ways 2016 Kicked Me (And My Business' Ass)

Highlights: Launched online store & created an entire set of digital products, switched my business model from freelance writing to blogging-as-a-business, started doing affiliate income like it was literally my job, self published my first book The Millennial Homeowner, then got a traditional publishing deal. (read about both of those developments here!)

I began 2015 in the highest of hopes. It was my first new year working for myself and I even sat down and wrote my very first strategic plan to try and guide what I wanted to do over the next 365 days. Sadly, despite the best of intentions, I fell short of a lot of the bigger business objectives. I didn't make six figures this year, over invested in my business (yes, there is such a thing) and shied away from speaking and media for the second year in a row. Entrepreneurship is easily the hardest thing I've ever done, but here's what I learned.

You're Probably Not as Good at Outsourcing as You Think

This is actually something I learned just last week as I was reviewing my Trello cards. Trello is a task management/collaboration tool I use to run my entire business, and the best part is that at the end of the year you can easily review every task completed. I went back and looked at what I'd accomplished in Trello. There had been some big wins (building out products and promoting affiliates mostly) but I was still deeply mired in the content creation and running of the site.

I finished the year feeling frustrated about not having enough time to accomplish what I'd really wanted. Even though I outsource, I wasn't doing it enough.

Now I realize I need to do this more, even if it goes outside of my comfort zone.

Ask F*cking Questions

Put me in a room and I'll ask all kinds of probing questions: the ones about your life, your interests, your problems. After all, questions and answers are how we learn about the world and what's around us.

So it's always surprising, especially to me, that when it comes to business arrangements, contracts, and working with others that I barely open my mouth. This is a huge mistake I made when I bought my first home (and I wrote about how to overcome this mental block in the book), but I found myself “quieting down” over and over again in my business dealings this year.

What the f*ck? This is no way to #GirlBoss.

Since I'm big into 30-day challenges, I decided to try something new. Now, with any type of transactional interaction, I push myself to ask a question. Even if it delays my response time, I ask a question. I'm no longer accepting things (or people) at face value.

This is what challenging myself to ask a question does – it makes me sit up, lean in, and pay attention.

The Need to Be Gentle

By this point I've written  ~700 words about the mistakes I've made in my business this year. But the words in this blog post are scant compared to the thesis paper of self-doubt I've written in my head over the last year, with the critique hitting an all-time high this winter.

A few months ago, I was in the shower and running over a list of all the things I'd done wrong in my entire life. That time I accidentally stepped on a baby bird when I was a kid? Forgot to send a holiday thank you note? That joke I made at a networking event last week that didn't land? There I was giving myself the what for when I was simply trying to grab a quick shower.

“You have to stop doing this. It's so unproductive.” I said to myself. “Quit that!

That was a big realization moment for me.

How many of us go about our daily lives, functioning at a high level, with a constant hum of anxiety and self-criticism on low in the background of our thoughts? For me sometimes, it feels like a TV I can never turn off and it's been on the same channel for almost 30 years now.

And quite frankly, I'm sick of it.

These thoughts serve no purpose, and while it's important to be kind and gentle to others, we first and foremost need to be kind to ourselves. (This mentality of gentleness is also one of my core money beliefs!) I can only imagine how much this has impact my mental and emotional bandwidth that could've been used for other projects this past year.

In my attempts to be more strategic, productive, and profitable in 2017, this critique is the first to go.

Don't be Afraid to “Let Go”

“Letting Go” applies to everything: your job, your relationships, your money baggage.

In my own business, I was terrified of rebranding to something other than “L Bee and the Money Tree” and I let a lot of other people's opinions on this sway my decision. To be honest, I'd been thinking of rebranding off and on for over two years. I finally pulled the trigger because I'd settled on something else I could live with (I was very adamant about not rebranding to my name, although I know this is the accepted best practice.)

Letting go of that identity (both online and off) coupled with fear over whether or not the re-brand would fly kept me in a locked-up holding pattern for the second half of the year. Finally, I got so fed up with the lack of progress in my business that I decided to re-brand, seemingly overnight.

Now, after eight weeks of hard work with developers and my team, I have this shiny new website that I love and a well-curated library of (what I consider to be my best articles) from the last five years.

Even though it's too soon to tell if the rebrand has been a smash in terms of commercial success and traffic, I already feel better having a brand that I feel is truly reflective of my beliefs about money and my personality. I always felt so hamstrung in trying to make LBMT sound credible despite the slightly immature name. Now, with the sleek branding, I feel like I can (once again) let my personality return to the writing, which is really what I love most anyway.

(5 swear words and counting in this post alone.)

So, even though it was scary and hard to change everything from “L Bee and the Money Tree” to “This Woman Trying to Live Her Financial Best Life”, I learned that in letting go you always make room for more good. There's so much beautiful, empty, blank space to fill now and I love that!

So, whether it's letting go of negative feelings about yourself or another person, letting go of conceptions about what you think your life is supposed to look like or simply letting go of items around the house, I encourage you to do more of it in 2017. Push yourself. You already know what needs to go, but dig deeper. Half the sh*t in our lives we really don't need.

(Six swear words and counting…)


I had a lot of fun in 2016.  (See my insta for proof!)

Highlights: TOOK A DREAM TRIP TO ITALY in November, performed in two shows, went to NYC (again) for a week, Moved from my house into a beautiful new apartment (Read about that here), Went blonde (they really do have more fun), Named to Atlanta's 30 Under 30, and dressed up Roo for Halloween.

Share: What's the biggest lesson you learned this year?

  1. Reply

    “I’m not sad to see the b*tch out” hahaha. I love how you keep it real. You seem to have such tenacity for pulling through situations, you’re kinda a rockstar.

    Congratulations on the Atlanta 30 under 30!

    1. Reply

      Thank you Colin! I’m glad it seems that way. Sometimes I feel like I’m always saying what bad happened and how to overcome. I’d like one year at least full of happiness and that’s what I’m striving for in 2017!

  2. Reply

    I feel so much of this! Excited to see what’s next in 2017, yay!

    1. Reply

      I thought of you when I talked about outsourcing and the asking questions part – you’re so good at both!

    • Dia
    • December 29, 2016


    1. Reply

      Thank you!

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