I only have a few entrepreneurial regrets, and losing my ability to do deep work is one of them.
This was entirely avoidable, had I just been more aware that it was happening and taken action when I noticed it. But I didn’t, and so now I am working on rebuilding my deep work “muscle”.
When we first founded ion, and there were no employees yet, I did a lot of short duration, shallow work, like making cold calls, responding to emails, scheduling deliverables, writing estimates and light bookkeeping. I also did a whole lot of deep work like writing multi-million dollar proposals & contracts, creating presentations and coordinating massive multi-month project plans.
I was equally comfortable with either type of work—from jumping around a bunch of lightweight tasks and quick context switching, all the way to ‘going off the grid’ and putting my head down for a day or two to work on something substantial.
As our company started to grow, this continued. I was planning, I was writing, I was reading 60-page documents…but there was now a lot more shallow work, and a lot of jumping in and out of meetings too. I was context switching more than I ever had before.
Thinking back, I see my ability (or lack thereof) to do deep work in an arch that tracks to the growth of the company. As we grew, I wasn’t doing the deep work, I was supervising the people who did the deep work. I personally had fewer and fewer pressing reasons to do deep work, because I was so internally focused. My days were spent engaging with our teams, and reviewing the results of their deep work. I was no longer working on deliverables that were purely mine to execute or that required me to put my head down. In fact, quite the opposite, my head was always up, scanning the horizon of our employees, prospects and customers.
What I was doing was important, don’t get me wrong. It just didn’t require me to dig in and think through something tricky. It didn’t require to me get into a flow state.
It’s hard to admit that.
I don’t blame the company, or the growth. I blame myself and the choices I made that let me slip into this distraction-filled, adrenaline-fueled existence. A company needs its leaders to do deep work, so this was definitely a shortcoming of mine. I was allowing the shallow, urgent work take all of my attention, and lulling myself into thinking that was my job.
Shallow work is easier, isn’t it? I mean, our lizard brains are wired for the distracting stuff and our attention spans are quickly dwindling to be shorter than than a goldfish*. This happened to me, and I let it. I got sucked in meetings, and putting out fires. I was no longer creating anything. I was spending my days with my people, which is what I felt I needed to do. Unfortunately, I did at the sacrifice of my ability to engage in truly extended, grittier work.
What are the symptoms of losing your ability to do deep work? You already know, because so many of us are grappling with this. For me, it’s obvious. I work on something for 10 minutes and then jump to the next thing. Or I get distracted.
Checking email, popping in for a quick chat on Slack, looking at social media and skimming headlines are the candy of our digital generation.
When I need to sit and think about a new or tough issue, I noodle for 10 minutes and then check my phone. When I have inspiration for an article, I sit down and bang away at the keys for a few minutes while the ideas flow. As soon as I get to a tough spot in the article, I find myself unable to dig in and get through it, so I wander away and on to something else. I rarely, if ever, get into a flow state.
In the back of my mind I knew this was happening, and I didn’t love it, but I wasn’t too worried about it either. I didn’t really think it mattered.
Turns out it did matter. For two reasons. One, because I came to miss deep work and the outcomes that came along with it. But even more importantly, when I did need to do deep work, I got stuck in the mud.
The first time I realized that my deep work muscle had gone too dormant was when the due diligence process for our acquisition started.
There were hundreds of items to gather and prepare for diligence and I had a ton of them assigned to me. I jumped right in. On the easy stuff. On the stuff that only took 5 or 10 minutes. And I was excited to tackle the tricky stuff too. This wasn’t about procrastination. This was about hitting a wall every time I sat down to prepare one of the meatier diligence items. It wasn’t that I didn’t want to do it. It’s that my mind literally felt like cement. Like the ball was sitting at the top of the steep hill, but not matter how much I pushed it, it would not go over the precipice and start rolling down.
I knew I hadn’t been doing deep work over the past few years, but I didn’t realize that the effect was going to be losing the ability to do it.
I don’t want a life spent jumping from one distraction to the next, professionally or personally. I want my deep work muscle back, and I am resolved to do so.
I’ve been working on this in earnest for the past few months. There have been four key things that have helped me start to slowly regain my ability to do deep work:
- I treat some of my shallow work as deep work. Just for practice. For example, I could do some light social media triage and engagement sprinkled throughout the day. Instead, I schedule it for an hour once per day, and I force myself to stay engaged with it for the duration. Even though it’s not deep work and I don’t need to put my head down to do it, I’ve found two benefits to this. First, the time I am spending is more meaningful and the fruits more rewarding. I learn more, engage more, and come up with better ways to use social media for myself, my brand and my company. The natural outcome of giving shallow work more time is that it gets more real attention and that makes it more rewarding. The second is that it forces me to stay focused on a single initiative for more than a few moments at a time. I love doing this with social engagement, because it’s normally very shallow work for me. Changing how I do the work is helping me grow back into my ability to do actual deep work.
- I time box. A lot. Ironically, I love time boxing to make sure I don’t spend too much time on something. Like, when I need to organize my closet, something I love doing, I will time box myself to 20 minutes so that I don’t get sucked into a day-long extravaganza. Or at work when I have a big meeting with group discussion on many topics, I will time box so we stay on schedule without going down various rabbit holes. Time boxing can be fantastic at making sure time doesn’t get away from you. But now I know it can also be fantastic at making yourself stay focused for longer durations. If I need to work on a tough topic, I just set a timer for 15 minutes and dig in. No matter what happens I don’t check email, look at my phone or get into a side conversation. I just focus for 15 minutes. I do not let my attention waver to the obvious mindless distractions during the deep work time box. At some point, I start to thaw and a little bit of a flow state starts. So, I do my deep work for 15 minutes (and let’s face it, 15 minutes of anything isn’t deep work at all, but remember that I am broken and taking baby steps). Then a little bit later I will start again, setting the timer for 20 minutes. I just keep expanding the timer until I’ve worked my way up to 30, 45, 60 minutes and longer. It’s not easy and I am not perfect at this. Sometimes I can’t even do it. But this timer tactic has absolutely helped me stay focused for longer and longer durations and I am able to ease myself into a flow state and deep work without as much angst now. When I get to a tough cognitive spot I don’t crumble and jump over to headlines or instagram. I just dig in and keep on moving forward. The muscle is getting stronger.
- I leverage my calendar. A really simple idea, that lots of people use. I am scheduling my deep work time, to guilt myself into doing it. I never was one for scheduling my tasks, probably because running my company the calendar was jam-packed, with back-to-back meetings everyday (the meeting culture is a topic fo another article!). I just didn’t think it would help. But I have been trying it—scheduling planning time, writing time, client deliverable time, etc, and it’s helping me. When the calendar says “drop everything and work on X for the next 2 hours” I am finding myself complying more and more.
- I read physical books. This has been an unexpected help. I love reading. And I love books. Physical ones. But I quickly adapted to digital books and haven’t bought a physical book in many years. Because I am a voracious reader, I love the portability of iBooks and Kindle, and read whenever there is a moment of down time. But, I’ve come to realize I rarely sit down with a digital book and read for an hour, or two, or three straight. My mind wanders too much. My reading has become snacking, not a meal. Which isn’t like me. When I recently picked up a physical book, on a lark, I brought this same bad digital ‘snacking’ behavior with me. I would read a page or two and put the book down. I blamed the book. But the truth was, I liked the book and I was picking it up many times a day. Losing my ability to do deep work has transferred over to reading, something I really love doing and can get lost in. So, I just decided to force myself to read. And read, and read. And just not put the book down. It wasn’t easy as first. My head hurt. I was angsty and restless. I was hungry. I was thirsty. I was so damn crabby. And then, all the sudden I wasn’t. I started to enjoy it. I stopped thinking about how much time had passed. And the more I do this, the more it is helping my deep work. I believe changing my reading habits has improved my ability to concentrate in my writing, research, planning and problem solving.
I’m definitely making progress and I’ve made a personal vow to not lose this ability again. I think company leaders have to do the deep work—it’s how they set vision, roadmaps, long-term goals & plans. It’s how they think through tough issues facing the business. Deep work creates the gas for the engine of the company, and fuels the engagement of the staff, the press, the investment community, the customers and the prospects. It’s how the hard stuff gets solved, and the innovative ideas take root. Deep work weaves a rich fabric for the company to rely on in its day to day—it creates the very stuff that other stuff is made of. It’s important. So I am making a conscious choice to cultivate it.
*The whole “our attention spans are now shorter than a goldfish” thing has been debunked. Many times. But it sure feels like it’s true, doesn’t it?