How to become more offensive

Two weekends ago I listened to the Tim Ferriss interview of Chris Sacca. Sacca is an early-stage investor in companies like Twitter, Uber, Instagram, Kickstarter, and many more. He's a fairly well known dude. The best audio I've ever heard from him was of him crushing Alex in the Startup Podcast, where he perfected Alex's own pitch for him because Alex was too nervous, and then told him it was a horrible idea. 

In the Tim Ferriss interview, Sacca explained why he moved away from Silicon Valley. Sacca moved to Lake Tahoe at what many would have considered the absolute worst time for him to leave the Valley. He had just lost a ton of money, he was still relatively young and unknown, and he was leaving the most connected area in the world for software startups and investors (aka his job). 

While Sacca was living in Silicon Valley, he had to be defensive with his time. He constantly had people asking him to grab a cup of coffee, to hear their pitch, to give them feedback, or to attend an event. All of his time got sucked up by other people. Even if he said no to the obvious events and people that were a waste of time, his time still got consumed by "legitimate" events and meetings with people he knew and trusted. He was just too connected. While he was being defensive, he found that he wasn't actually getting anything done. 

Part of the reason Sacca moved away was to get the time back, so he could be more purposeful with what he did. He called it, "playing offensive." Instead of constantly defending your time, how can you make space in your life to move to a purposeful offense. If you had more time, what would you do with it? What's your highest and best use? 

Lake Tahoe is around three hours from the Valley. That turns out to be the perfect response to people asking for coffee, drinks, or time. Sacca still said yes, he just told them they needed to travel to him. It was the perfect filter. Most people won't be willing to make that type of commitment. So only the most serious people followed through on the trip out there. 

With his new found time, Sacca pulled himself out of dept. Doubled down on startup investing and advising, and is now running what might be the most successful investment portfolio in history. He's crushing it. And he points to figuring out how to "play offensively" as one of the most important factors. 

Since hearing this podcast, I've been thinking about this a lot. I'm very defensive with my time. I have a never ending stream of meetings, requests for time from clients, requests to pitch from prospects, meetings to explore partnerships, networking events to attend, etc. Never-mind the emails that go with all of that, the commute, and trying to find time to workout. 

I'm guessing I'm not alone. I can imagine you have tasks and activities that make you defensive with your time. I know you have emails, meetings, and I know each role has it's own set of tasks that take up time, but aren't the "core" way that you think you add value. It could be as trivial as time entry, or it could be a regular report you need to put together (ems), a pull request (devs), a regularly scheduled Twitter post (marketing), or something else.  (I just assume that the designers love everything they get to do.) 

We all play defense. It sucks. But it's certainly part of the job when we work as a team. As we continue to grow, the more defense we will all have to play. So how do we handle that? 

At the last Monday morning meeting at DeveloperTown, Aaron Lerch shared some of his strategies for how he manages some of his time and attention. It included tips for email, Slack, meetings, and the dangers of multiproject multitasking. (Side note, I just changed my preferences to disabled emails from Slack. Thanks Aaron!) 

As for me, I'm not sure yet. I've been thinking about it for two weeks now. I don't have the answer yet, but I have some ideas. Here's what I'm doing to try to become a bit more purposefully offensive with my time: 

  • I'm going to reread The Effective Executive by Peter Drucker. I first read this book over ten years ago. I remember the themes, but not the specific details. I think it's time for a refresher. The basic premiss of the book is that all knowledge workers are executives. And executives need to prioritize effectiveness over efficiency if they want to be successful. 
  • I'm going to only check email a couple times a day. While that turns out to be very difficult to do in practice, I'm trying out a new tool called Handle that I think will help me do it. It integrates with Gmail, and has a view that completely hides your inbox while still allowing you to work on tasks and priorities. I've been using the free version for a couple of days, and so far I really like it. I hit inbox zero for the first time in over two years, and I have a clear list of to-dos that have been prioritized and assigned due dates. 
  • I'm going to try to be more purposeful with my days. I'm planning to start each day by listing the top three to five things I want to accomplish that day. And then my plan is to not leave until those tasks are done. If I can't manage to that effectively, I'll shorten the list to the top one or two things. My goal isn't to end up staying at the office later, but instead to train myself to remain focused on those goals throughout the day so I become more protective of my time to actually get them done.
  • I'm going to experiment with sending my peers a short email status each week. No one has asked me to do it. But I think if I can come up with weekly goals, it will help me figure out what my daily goals should be. I'm thinking a short list of bullets - nothing fancy. If I have to take the time to report progress to my peers, then I think it will help me remain focused on those top priorities. Ideally, most of what I'm reporting on each week should roll up into the larger plans we set as a management team. 
  • I'm going to start to ask for help more frequently. I don't need to do everything myself, and in many cases I'm not the best person to do certain tasks. I'm going to try to be more purposeful in handing off tasks and responsibilities to the people who are best equipped to handle those tasks. This is very difficult for me. I suspect it's difficult for all of us to ask for help, and that none of us is doing it enough.  

So that's my starting plan for my new offense. I doubt I'll stick with all of those, but hopefully I'll make some progress in figuring out what works for me. 

If you have some techniques you use to better manage your time/attention/focus, you're welcome to share it below.