For the first time in a decade, I’ve procrastinated writing this annual reflection which feels like a treasured time capsule.

After last year’s 77 pager (with pictures), it felt like a daunting task.

So, I’m giving myself permission to share it in a more crude fashion, so as to complete it. Why? Because I believe that done is better than perfect.

So, although it’s already 3 months into my 35th year, I’m compiling a bulleted list with what I did, how I grew, and what I learned.


As I share every year, I do this for a few primary reasons: 1. To have for myself to reflect back on, 2. To commemorate the moments (big and small) that happened over the previous 365 days, and 3. Because each time I share it, others say it sparks in them some version of the same practice which often results in gratitude and more intentionality in how they spend their time in the upcoming year.

Sharing what I learn is important because if my experiences can offer any amount of truth, inspiration, or guidance to others, I’m all for it.

So, let’s dive into that which was 34…

-At the start of the previous year, I was still living part-time in NYC until Brendan officially moved to ATL in January.

-I was honored with Atlanta’s 40 Under 40 award days before my birthday. When asked what the best advice I had to offer was, I shared: ‘Don’t take yourself too seriously’.

-Brendan and I have birthdays one day apart (plus 6 years) so we hosted a joint celebration in ATL and then in Brooklyn.

-I got frustrated with people asking shitty questions when they meet new people so I published ‘The 55 best questions to ask to break the ice and really get to know someone’, which was read over 1.1M times so far. Apparently I’m not the only one who wants to have more meaningful conversations.

-Got to read a dedication I wrote during the ceremony for the wedding of a couple I set up— one of my greatest life accomplishments!

-Spent Thanksgiving in Vancouver with family.

-Post family time, Brendan and I got cozy on the Sunshine Coast (picture Xmas tree forests with waterfalls, fireplaces, and home cooked meals).

-Re-opened some old family wounds and experienced deep pain as a result. Learned that being right doesn’t always mean things go your way. I was also reminded that being an adult child is hard and that family relationships can the hardest.

-Spent months upon months diving into myself to uncover what was at the base of a nagging feeling I felt that there was a new incarnation of my career coming, but I had to do the work to figure out what it was. After a lot of soul searching, I realized it was the need to share what I’d learned about how to intentionally design my life so others could have the resources, tools, and inspiration I’d compiled and learned over the years.

-With that, I had to decide how. Recognizing that I always knew that after writing my kids book, I’d one day write at least one adult non-fiction work, I spoke it to life and said, ‘I’m going to write a New York Times best-seller’.

-I kid you not, within weeks, I went from having no idea what to do next, to have meetings with 5 literary agents, getting offers from 4 of them, and signing with one of them.

-Because of that, I learned a lot…fast…about what it takes to get a publishing deal these days and to write a great book. So, I set out to do many of those things: hired a writing partner and started to grow an audience via a personal brand (both to demonstrate to a publisher that I had people listening who would want a book from me, as well as to get to know who my audience really was and what they really needed).

-I was a podcast guest a in a nationally syndicated radio show’s studio.

-AJ, my older bro, finally got to cash in on my earlier birthday gift and have, as he said, one of the top experiences of his life: photographing a Miami Dolphins game, on the sidelines, with the official NFL photographer..best gift I’ve ever given.

-I started to have more challenges with one of my companies, Network Under 40, as I felt myself growing apart from the core audience and as my life changed, I felt tension with running it. This showed in our numbers.

-I got smatterings of pictures and stories all year from families who used my book to teach their kids about financial responsibility. They made me so happy to know that even though it’s not a primary focus for me right now, that my original mission is still in effect!

-Spent my first Xmas with Brendan’s family in Cape Cod (and even learned that they had the same random tradition of doing scratch-offs in their stockings).

-Made some new friends with whom we spent New Years Eve in a cozy North Georgia cabin… those friends are now some of my most dear (a reminder that depth of relationship doesn’t always take a long time).

-Celebrated so many beautiful milestones of my friends: promotions, new career endeavors, entrepreneurial successes, engagements, weddings, babies, and even ending the wrong relationships.

-Took an epic journey by Hiawatha train from Seattle, Washington to Whitefish, Montana, to celebrate a friend’s 50th.

-The fun didn’t stop there- we snowshoed in Glacier National Park and enjoyed the snowy festivities. This also marked my first National Park experience, resulting in my vow to go to more.

-As I got deeper in my knowledge of what it takes to grow a following with a personal brand (working towards the long-term goal of NYT best-seller), I decided I needed to hire a marketing virtual assistant. It was tumultuous, and I made several poor hiring decisions until I didn’t, and found a gem….and then she resigned around my birthday and thus, the challenge to find a new one began. A reminder that the people beside you in your company are so important, and often the biggest challenge to running a business.

-Surprised my mom in SF with my siblings for her 70th birthday.

-House hunted..a lot..and waited for the right fit—and was oh so glad we did because our house is exactly what we wanted! And honestly, I hadn’t realized after living my entire adult life in my first home, how much a change of environment and location can shift your energy!

-The designer in me loved decorating a new house—and as I do— finished it in a week’s time, thanks in huge part to my stylish mom who came and helped pull it all together.

-When I was younger, I was really into black and white film photography. In high school, my art teacher pulled me aside to try to convince me to go to art school instead of Emory. I didn’t, and as I got older, photography became something I did less and less. And then I realized that as I needed to create more photo content to pair with my audience-building goal, I got to re-imagine the way I love photography and art direct myself …even if just for Instagram!

-Got to stand back and watch Brendan’s career grow and see him shine when he launched Forbes Impact…which felt like the proudest stage mom moment!

-Celebrated the weddings of both of my female cousins and in turn, welcomed two incredible men to our family.

-Globe-trotted to many corners of the earth, 12 countries I think… and even literally ran into my older brother AJ on the street in Singapore!

-Walked down memory lane after my parents moved out of my childhood home, first to South Florida, and now to Panama…and as a result, gifted me all of my childhood memories

-Felt a lot of nerves saying yes to facilitating an allstar crew of leaders on a Reality Israel trip (and was so glad I did). Made some lifelong friends and grew a ton as a result. Lessons from it: stop playing small and borrow the confidence that others have in you until you can believe it for yourself.

-Pondered my relationship with time and discovered that I can be a time creator. This is a longer story…

-Accidentally landed my first-ever consulting project to help a private high school develop and execute their first alum engagement strategy.

-Had my first professional photo shoot and first professionally designed personal branded website.

-Dedicated time for the 11th year running as member Emory’s Board.

-Was a guest on dozens of podcasts.

-Interviewed celebrities for the first time. At first I was terrified, and then I got really comfortable and discovered how much I enjoy doing it.

-Dabbled in launching a side project with a new contact and learned that it wasn’t synergistic. Out of that I gained a lot of confidence and turned a pitch into a new best friend.

-Stayed open to the Universe delivering incredible, inspiring new friends—and received it immensely.

-Wrote 30+ articles which were read about 1.5m times in Forbes, Thrive Global, Bossbabes, and other outlets.

-Spoke at many events.

-Hosted 70+ Network Under 40 events in 4 cities.

-Tried acupuncture.

-Kept treating myself to eyelash extensions, hair treatments, massages, mani/pedis, etc…because it feels good to pamper yourself!

-Was hired as an ‘influencer’ as well as an on-site correspondent for Chase Bank…which I learned I loved—and got paid to learn a new skill.

-Supported local events on art, race, and hunger.

-Launched my first virtual course to much success (and executed it for 4 weeks while physically in a different city for each broadcast).

-Attended 7 weddings of beloved friends and family.

-Became a landlord when I rented out my first home.

-Hired a personal at-home trainer…for 2 sessions.

-Read 38 books.

-Got to introduce Brendan to my best childhood friend and his wife over a weekend in Denver…first boyfriend who got his seal of approval 😉.

-Dreamt up a virtual summit to connect with a new audience, launch my brand, do research for my book, deepen relationships with thought leaders in the space…and had never attended let alone thrown one. Was one of the most challenging processes I’ve taken on in business. It took 3x as long as I’d estimated and 5x as much money. But, we had 7,100 people attend from 16 countries, had 45 of the world’s top leaders (like Deepak Chopra, Adam Grant, and Jen Sincero) teaching, attendee feedback was so heartfelt and grateful, and on top of that, I doubled my investment!

-I learned how to interview for the first time through that process and realized that my curiosity and love of question-asking make me the perfect person to do it! That plus I can empathize with the audience to estimate what they’ll want to know and ask that. Oh, and Deepak Chopra was my first ever live interview.

-Went to a polo match for the first time. Made a Pretty Woman reference like a rookie.

-Went to the Masters and had dinner with golf legend Gary Player, then interviewed him.

-Sat courtside at a Hawks game and the mascot aggressively made out with me, much to my dismay.

-Hosted countless parties and dinners in our new home.

-Life changed into a walking-centric one when we moved. We even got rid of my car for over 2 months to experiment with life without one (after getting paid out by Audi to give my car back thanks to their billion dollar legal settlement). We ultimately got a car.

-Mentored at a Startup Weekend, as well as got a co-mentor for myself, and found ‘mentoring moments’ for both my gain and the gain of others.

-Joined another board and turned down a board seat.

-Was a guest on a show that filmed in a real life tv studio.

-As a result of one of my podcast appearances, a reputable publisher heard me and reached out to inquire about working together (and their past clients include 4 of my favorite authors)…it’s all coming together!

-Went to my first Atlanta United Game (now MLS champions).

-As usual, fitness was my weakest point. That said, I got in some yoga, stand up paddle boarding, 10k steps a day for a while, pole dancing, acro yoga, and park walks.

-Took the leap and hired someone to take over my in-person role for Network Under 40 in Atlanta. The hardest part was letting go of control.

-Finished edit 1 of my book proposal…only to get a swift kick in the rear by my agent who wanted hella edits.

-Got way more confident in my own skin.

-Walked up to a comedian (Nikki Glaser) after her set to invite her to do an interview. She said yes, which was a reminder that people are generally open and the worst they can say is no. Plus, when you’re offering something of value, your chances of getting a yes increase substantially.

-Learned that I actually am a really good manager (previously thought I wasn’t because I like to move so quickly and don’t like to worry about fluff over outcomes) when I believe in people and they believe in what I’m building. Was so fortunate to work with some allstars this year who helped me to be a better leader.

-Spoke to a group of inspiring high schoolers.

-Expanded my ideas of what is possible.

-Brought on bigger name and bigger dollar sponsors than ever before for my companies.

-Experienced more stress and anxiety than I recall since when I first started my businesses 10 years ago, all thanks to a shitty hire I made, which turned into 6 months of delays on my virtual summit, a lot of money tied up, and a lot of fear over the impact it could have on my reputation and relationships.

-Lawyers got involved and guess what— it all worked out!

-Lots of concerts and cultural moments (Music Midtown, Lauryn Hill, Christina Aguilera, Aladdin the musical…to name a few.)

-Learned so much about digital marketing, funnels, personal branding, and growing an audience.

-Got hired again by Chase to attend Inc 5000 as their influencer and on-site correspondent.

-Brendan’s sister came for a visit.

-Piloted a live virtual course, got feedback (and got paid to test it), and then built out an evergreen, fully digital and self-paced version to teach others everything I’ve learned about hosting networking events so they can host their own.

-Watched a ton of documentaries (and reality tv)… a girl’s gotta turn her brain off and decompress!

-Started recording episodes for a limited-series podcast with my friend Elizabeth who is the #1 podcaster for food and wine.

-Celebrated when best friends moved back to Atlanta.

-Welcomed my first nephew to the family!

-Became more of an introvert and had to erect new boundaries to protect my energy.

-Spent a beautiful Thanksgiving with family in Santa Fe.

-Went on a road trip to get more connected with America and visited The Grand Canyon, Painted Desert, Antelope Canyon, and Horseshoe Bend.

-Lost my Paris virginity… a place I’d held out on visiting for a ‘romantic adventure’. It was everything I hoped for–except for the violent protests…

-Spent a few nights in the only place on Earth where I care about food more than anything else (Rome).

-Flew straight to Miami for one night at Art Basel.

-Then, straight to Esalen (Big Sur) for a couples retreat.

-Celebrated our first Xmas in our home together with Brendan’s family who came for a visit.

-Departed for a magical new year in Guatemala.

-Followed my instinct to email the people with whom I’d collaborated this year and within minutes, Deepak wrote me back. Within 20 more minutes, we decided to launch a video series in January 2019 called ‘Diving Deep With Deepak & Darrah’ which is now live.

-Decided to channel my nerves into action.

-Began to trust myself more and doubt myself less.

-For the first time ever, instead of making a laundry list of goals, visions and mantras, I committed to one thing for this new year: to have fewer goals. Why? Because I want to allow life’s opportunities to guide me where I’m needed (and because drive is not something I lack). As someone who is dangerously focused on doing anything to which I commit (even to myself), it feels expansive to let go in this way.

-Because of that, I’m learning a lot about having an intention and releasing the expectation of how it will play out.

-I can say, without hesitation, that I’ve never felt more self-assured. While my self-doubts haven’t disappeared, I’m finally realizing that everything I need is already within me, and it’s my responsibility to unearth it and share it.

-You can only be what you’ll allow yourself to become. I was reminded time and again that my limitations are my own doing and that I need to dream bigger to achieve bigger, and more so, to keep growing and serving.

-Was reminded that any time I’m stuck in a rut or down, the best medicine is to do for others.

-Was unafraid to advocate for myself and speak up for my needs in ways big and small.

-The power of patience and persistence are key. Through exercises like this one, I can see how doing the work, day in and out, is what it really takes to create whatever you desire.

-There’s hella power in ambiguity and uncertainty…yet we’re so often programmed to run from it. Learning more and more to sit in that discomfort.

-People are complex and multi-faceted. There are moments when I need others to give me credit if they’re just seeing one dimension, and I’m continually learning to offer the same generosity to others.

-Satisfaction/fulfillment/happiness isn’t a destination. It’s in the present moment and you have to slow down to recognize it.

-I am just one tiny person amongst billions on this planet, co-existing while we each live our own meaningful versions of life, which is a blip on the spectrum of time. On the one hand, this realization can be incredibly liberating. On the other, it can be entirely diminishing. And that’s just it- that murky middle where things can be both at the same time. It frees me from taking myself too seriously, all the while, still empowering me to make an impact.

-It’s important to do a self-check with social media and determine if the time you’re spending on it elevating you. When it’s not, I turn it off.

-Not everyone will ‘get it’ or will be along for your whole journey. That’s ok. There are seasons to relationships.

What would a year be without travel? Here’s where I went…in order:

-NYC

-ATL

-Vancouver

-Sunshine Coast

-ATL

-Nyc

-Cape Cod

-ATL

-Blue Ridge, GA

-ATL

-NYC

-ATL

-Seattle

-Whitefish, Montana

-ATL

-Nashville

-ATL

-SF

-ATL

-Playa del Carmen

-Mexico City

-Oaxaca

-ATL

-Hilton Head

-ATL

-Denver

-Del Ray Beach, FL

-Miami

-West Palm Beach

-ATL

-NYC

-ATL

-Augusta

-ATL

-Thailand

-Cambodia

-Malaysia

-Bali

-Singapore

-ATL

-NYC

-ATL

-Iceland

-ATL

-Israel

-SF

-Mendocino/Elk, CA

-SF

-ATL

-Serenbe

-NYC

-Cape Cod

-ATL

-Miami

-ATL

-LA

-Portland/Hood River

-ATL

-Barbados

-ATL

-San Antonio

-ATL

-Tulsa

-ATL

-Santa Fe

-Grand Canyon, Horseshoe Bend, Antelope Canyon

-Vegas

-ATL

-Paris

-Rome

-Paris

-Miami

-Big Sur/Esalen

-ATL

-Guatemala

 

34 by the numbers:

100,000+ miles flown

12 countries visited

25 months celebrated with Brendan

11 years of home ownership

10 years running Equitable Payments

7.5 years running Network Under 40

38 states where Equitable Payments operates

4 markets for Network Under 40

192 Network Under 40 events

8 team members

38 books read

30+ articles published

 

Grateful for another rotation around the Sun. For the lessons, the growth, the experiences, and opportunities.

And, if you read all the way to the end, shoot me a note- I owe you a congrats and thank you!

Until next year…