My Attempts at Deep Work – A Journal

deep work
How You Can Cultivate a Deep Work Culture: Part 1
May 11, 2018
career mapping
Episode 048: Starting With Yourself to Map Your Future
May 22, 2018

My Attempts at Deep Work – A Journal

deep work

Have you ever been wondering why you’re working so hard, but seemingly nothing gets done? Or you’ve made some forward motion, but can’t seem to break through to that next level? It feels like you’re always jussssst shy of the revenue number, the media placement target, the quantity of speaking engagements. It feels like you’ll never make it there.


Now of course, I fully understand that it can take 10 years to be an overnight success, so I’m not saying we all don’t need to learn, fail, learn again, rinse and repeat.  But a couple of years ago, I started to question this. Was this the only contributing factor? I mean, after all, I do all the right ‘business building’ activities, so what gives?


I slowly started to put together a hypothesis. What if I was incapable of doing the really mind-bendy work that makes a business really grow? Things like developing my unique voice on topics that matter to me (and thus my business) or continuing to delve deeper into more and more complex issues that face the people and companies I serve. What if I’ve totally fallen back on shallow work? Checking things off my list made me feel productive, so I hit the pillow at night feeling like I had ‘done something’. But as I realized slowly, those tasks were so….’tasky’, that they didn’t move the needle.


Looking back now, it totally makes sense why I was so hesitant to hire freelancers, especially a virtual assistant, to help me with my biz- I was so enmeshed in administrative and operational tasks that I figured I could just handle it. Well, certainly I could but that didn’t mean I had to. I just didn’t fully grasp that yet.


What follows is a loose diary both of recollections of days and me writing in the moment about my attempts for deep work.


May 30, 2016

I signed on at a co-working space today! Now work can really start to happen.


June 2016

I want to build a business where I’m able to reach more people and not have a 1 to 1 business, where I need to be personally present for every interaction.  I know, I’ll build an online course! Everyone’s doing it; why not me? I purchase a $1300 course on… how to build a course (Meta? Ponzi?) and I start methodically doing the steps. Step 1 is understandably about your course idea, and there’s good advice about how to validate your idea. I follow everything to a T.  I’m checking things off on the checklist they gave us- I’m feeling RAD!


August 2016

My business coach has been begging me to hire help for like, a year now, and I can feel her advice go in one ear and out the other every time it comes up. But as I sit here at WeWork doing all the tech and videos for my online course, I almost throw my laptop off the patio into the beer garden below when I lost about 2 hours of video work. But, it’s within my skillset to just do it again, so I stay a couple hours late to re-do the work.


October 3, 2016

I’m getting married in a month, and realize there is far too much to do with the course (along with other parts of the business!) to do alone, so I hire an assistant. Let me say that in another way: the only reason I finally listened to my business coach was because I was planning a wedding and didn’t have time. If I were still single, I don’t think we’d be having this conversation right now.


November 27, 2016

I’m back from my honeymoon and it’s kind of crazy how quickly I fall back into old patterns. I have to grudgingly find things to give Leigha, my assistant, to do, because ‘I can just do them for free.” Oh boy, we’ve got a stubborn one, ladies and gentleman!


December 15, 2016

Luckily, Leigha is a magical unicorn and as I start to review her time logs, I realize she can do things I absolutely loathe doing in 1/7th of the time. I’m not exaggerating. This helps me give her admin and ops tasks to do and clears my plate, but instead of using that extra time to do the deep work, I pile more and more on my plate.  I think, if she’s doing all that, I can speak at more events, write more posts, go to more networking meetings, schedule more phone calls, actually attempt social media, start a Pinterest page (WHY?) , etc.


January 15, 2017

The course is not the panacea I thought it’d be for many reasons. What I didn’t realize back in the summer was that there is no blueprint for original thought. What I mean by that is, that while it’s all well and good to test and validate your concept and follow some steps in a course about making courses, if the original concept doesn’t come from deep, hard, aha-moment thinking, you don’t have a leg to stand on. Getting people’s takes is part of it, but rely too heavily on that shallow work and you’ll be a fish out of water. I feel like I just wasted 6 months, and crippling self-doubt of ‘can I hack it?” comes back to stay for awhile.


March 8, 2017

To add to this, everything comes to a screeching halt when, after a couple of weeks of dull pain in my right temple, the pain explodes into the most intense pain I’ve ever felt in my entire life. It turns out all my hustling and grinding was literally translating to grinding my teeth so much that I have an acute TMJ episode for a month or so. I am unable to work for most of this time.


March 30, 2017

I am venturing out into the world again, and decide to spend the afternoon at the Museum of the City of New York. As I’m walking through the exhibits, I realize I’m making really deep connections between the exhibit and the work I do. It was startling at first. I realize I’ve created the space to allow such connections to be made, something that was brand spankin’ new in this brain (I was once called the Most Efficient Person of All Time, which is not the compliment I once thought it was). Intrigued, I take a break from the exhibits to grab a tea and I start to jot down some quick flashes of ideas. Bottom line: It becomes really clear to me that the hustle hard approach isn’t working for me.


April 16, 2017

I am at restorative yoga, something that was recommended for the healing, and someone walks in with a tshirt that says “Namaste & Hustle” or some such garbage. Since my newfound realization at the museum, I visibly bristle at the term ‘hustle’.

I’m changing slowly, but I don’t quite realize it.


Fall 2017

It’s been a few months since that goldmine of a realization hit me, but not much has changed, besides my frustration levels. WHY haven’t I moved ahead ‘enough’? Yes, one could argue that high achieving people need to give themselves a break (I am absolutely guilty of this), but there’s more to it than that but I can’t pinpoint what it is. One day it hits me – part of the reason so many of my individual days go nowhere is because my morning routine – or lack thereof – is effed. I have been doing some good stuff for my body in the morning – stretching and myofascial release- but besides that, it’s a barren wasteland. I check my phone – email, text, social upon waking up and I get sucked into what’s in there. I used to think that was productive. After all, I am checking things off lists! Efficiency! I’d then eat a bowl of cereal and start work between 7:15 and 7:30am. I have my email open all day, so I respond to things as they come in, Corporate America Style. And I’m hungry by 9am again…and again at 11am…and on and on.


I begin radically questioning my morning routine. Every single second of it. I experiment with breakfasts, meditation, when I start work, phone checking, reading, journaling- you freaking name it, I experiment with it.


December 2017

I settle into a routine that works for me, plus gives me some morning quality time wit my husband over breakfast. In case you love hearing about other people’s routines to see what might work for you, here’s a brief run down:


6:30 am: Wake up naturally around this time, drink a full glass of water with my vitamins and probiotics, brush teeth, wash face.

6:40 am: Stretching and myofascial release

6:55 am: Cook breakfast for husband and me. 2 Sunny Side Up Pasture Raised Farm Eggs over a bed of organic arugula with roasted garlic sauerkraut (more probiotics), half an avocado, 2-3 shakes of Bragg’s nutritional yeast and about a tablespoon of olive oil drizzled on top. (Note: I’ve cut back significantly on gluten overall. I still have it, but it’s not a regular part of my week, and I suspect that’s helped matters.)

7:10 am: Eat breakfast and talk with husband; read a passage from an inspirational book (I love Tim Ferris’s Tribe of Mentors! I’ll read one person’s entry a morning and learn what other successful people do and how they approach life)

7:30 am: Husband’s gone; time to meditate. Some people advocate for doing it as soon as you get up, but it’s too distracting with him getting ready for work. I set the timer for 10 minutes.

7:40 am: Do my morning pages; Brain dump all the crazy distractions I had in those 10 minutes. It’s so interesting to do this after you meditate. I’ve realized some really damaging thought patterns I’ve had on loop that were definitely holding me back. Without capturing the thoughts right after, I would not have realized them as quickly.

7:50 am: Sit on my meditation cushion doing a seated stretch my yoga teacher recommends for my tight hips, and I read and take notes from whatever continuing education book I’m reading. Just getting a chapter in in the morning set me up to be humming with ideas all day.



March 2017:

I have been feeling good for months! The morning routine isn’t perfect and doesn’t happen the same way every day. But something is still missing. I’ve got the routine, I no longer am hungry an hour after I eat, I’ve got a team doing literally ALL the work I don’t want to do, so what gives?


On a whim and a hunch, I decide it’s time to get out of dodge and ponder these questions. I book a 5-day trip alone to Copenhagen, Denmark. I’m gonna bike around and think.


April 17-22

In Copenhagen, on a sunny side street at an outdoor café, I write an entire Ted Talk that I was STRUGGLING to write in my apartment in NYC in about 3.5 hours. And it’s pretty damn good. I read on park benches and bring my journal with me to capture my thoughts. I have rose in the middle of the day after biking around. And I start to have my own insights, an experience I haven’t had a lot in my working life. Not to say it hasn’t happened, but I’ve always taken other people’s work and internalized it or learned it. Blame it on the “memorize photosynthesis” types of instructions doled out in high school in the 90s, I guess. (Some teachers taught you how to think, but most didn’t, I’ve found. And I guess I didn’t take responsibility upon myself to learn that.)  Copenhagen was a good use of time and resources. Mission accomplished.


April 26, 2018

After CPH, I realize the next piece of the puzzle that’s missing from my incomplete setup. It’s that there’s only a very loosely defined plan each day, if at all, and I get sucked into checking email and Shiny Object Syndrome (ie, my phone right next to me)

So I start to segment my workday into 30 minute time blocks, something I learned from Cal Newport in his book Deep Work (which obviously spoke to me given my own realizations and hypothesis!) I incorporate breaks, walks and exercise and actually eating lunch while reading my book. So, I start following that, but keep a good degree of flexibility. Things come up and change, so I can rejig a current plan easily, but when there is no current plan, I can easily get caught up in how I was taught/programmed- checking email is productive, responding right away is helpful and is a badge of honor and being constantly available makes people like you. Woof, it’s easy to get pulled back into that life. It’s constant boundaries that keep me out of it….for the most part….


May 9, 2018

But not every day is awesome. I wake up and do my morning routine that’s been serving me so well. 6:45am But like with anything, a check of the phone can throw it all off-kilter.

7:30 am: Check texts, sit down to meditate

8:00 am: I am working on my Ted Talk this morning before yoga, and that’s definitely an activity where the phone should be kept far, far away.  But the phone is next to my computer and even on silent, it’s like I can sense when a text from the same conversation comes in. I’m distracted, and the time blocks I have set up for the day are already shot.

9:40 am: I was able to recover a little and am only 15 minutes behind my goals for the day. It’s time to leave the phone at home and go work at a coffee shop down the street.

10:45 am: That was an incredibly productive hour- I got some ideas written down, along with some potential blog posts and I continued to think of ideas for my big meetings tomorrow.  Yoga time!

12:55 pm: It’s after lunch and I’m feeling energized. It’s time to sit down and WRITE, YO.

12:57 pm: I’m uncomfortable in these clothes; I need to change.

12:59 pm: Oops, now I need water.

1:05 pm: Did Hollie text me back about doing something outside this afternoon? Fight the urge to go to the other side of the house where I left my phone and check.

1:07 pm: It’s stupid to spend time writing about my thoughts on the issues important to my people. I should be out there MEETING PEOPLE and HUSTLING.

1:08 pm: Crippling self-doubt about my choices sets in.

1:11 pm: Remind myself of my in-depth research that shows that our vicious shallow work cycles and Shiny Object Syndrome and “Hustling Hard” without much to show for it are MAJOR problems in our culture. And that I’ve witnessed it firsthand with the TMJ!

1:12 pm: Deep breaths, after I remind myself of all of that.

1:13 pm: Continue writing.

1:14 pm: Ugh the remnants from my lunch are starting to cake onto this plate. I NEED to wash it.

1:15 pm: Wash plate.

1:16 pm: Return to desk and without allowing myself to think a second thought, I write.

1:48 pm: I look up and it’s 1:48pm! 32 uninterrupted minutes of writing! It’s not perfect but I’m digging it. I keep going.

2:27 pm: I look up and 40 minutes have passed this time! I could get used to this! But I really wonder If Hollie and I are getting some wine today…..


So what’s next for me? I don’t quite know, but I know I’m onto something. To go back to the beginning of this post, what’s interesting, when you think about it, is that the elusive revenue target or # of media placements really isn’t what it’s all about. When you’re able to develop a deep-work-mindset and truly, truly start to do groundbreaking work, there’s way less, if any, hustling involved to get on reporters’ radars or meet with prospective clients. The work draws the clients in. The work brings the accolades from the press. So that means the work should be the goal.


That’s where I’m at right now. I haven’t ‘hit it big’ yet, nor am I making the money I made when I had my corporate role in finance, but I can feel it coming for the first time since I started my business, and that’s saying something (cue: days and weeks of crippling self doubt, culminating in crying hysterically in “Magic Mike 2” where there was one other dude in the theatre and he sat 2 seats from me, which made my hysterical crying pretty awkward).


I’m doing good work, I love my clients and I love seeing them succeed. And THAT, my friends, is the major shift that had to happen for me to truly be excited to see what’s next.