CHAPTER FORTY-FOUR

STAYING FRESH

Staying fresh has always been about three related things: staying mentally fresh for work; staying healthy; and making sure I have enough time for myself that's not about work. All of this plays into what Stephen Covey calls “Sharpening the Saw,” in his books The 7 Habits of Highly Effective People and The 8th Habit—both worth reading.

MANAGING THE HIGHS AND LOWS

I was reminded recently of one of my favorite entrepreneur sayings: What drives me nuts isn't the inevitable presence of highs and lows of running a new company; it's when they happen at the same time.

It's one thing to get used to the roller coaster ride of running a startup. That's part of the fun and the challenge of it all. There are great moments when everything's working beautifully. Your strategy is proving to be spot-on. Your team is executing brilliantly. Your biggest client renews and gives you a testimonial. Then there are the dark moments of despair. You're running out of cash. The new product release is behind schedule. A competitor steals a top client. No one lives for the lows but you at least grow to anticipate them and realize that “this, too, shall pass.”

The thing I can never get used to is when those highs and lows occur simultaneously. It just seems unfair. Let me enjoy the good news—whatever it is—for at least a day or two before clocking me with something terrible! But perhaps that's just another, even more poignant part of the humbling process that comes with running a startup.

The best way to handle the stresses of the highs and lows is to keep yourself fresh! One analogy I tend to use around the topic of keeping myself fresh is about running shoes. I usually get new running shoes every three to six months, depending on how much mileage I'm logging. I find the same thing every time: I may not realize I'm uncomfortable running in the old shoes but the minute I put the new ones on, I realize just how far the old ones had deteriorated and just how much better life is in the new ones. Same model shoe—just a fresh pair. I run faster, stronger and happier.

I often find that small tweaks to renew and refresh existing processes, relationships, thought patterns and work product make an enormous difference in the energy I bring to work and in the quality of the work I do. Recently, for example, I had two such events.

First, I did my periodic overhaul of my Operating System. I changed some categories and formatting, rethought some items, cleaned out dead ones, added some new ones. Voila! I went from semi-ignoring the system to running my priorities by it once again. I've had my most productive week in a long time.

Second, I completely rethought the dynamics of my relationship with someone on the team. It had grown stale. Check-in meetings weren't interesting or productive any more, just perfunctory. We sat down and crafted a new way of working together, a new list of topics we were going to tackle together that added more value to the organization. It was like a breath of fresh air.

These were minor tweaks, not major overhauls. And yet, they were as valuable—and refreshing—as a new pair of running shoes.

STAYING MENTALLY FRESH

I keep myself mentally fresh for work by maintaining a basic level of self-discipline. Having my act together in small ways makes me feel like I have my act together in all ways. It's a little like the “Broken Windows” theory of policing formulated by George L. Kelling and James Q. Wilson in the early 1980s: if you crack down on graffiti and broken windows, you stop more violent crime, in part because the same people commit small and large crimes and in part because you create a more orderly society in visible, if sometimes a bit small and symbolic, ways.

At Your Company

These are some of the ways I apply the “Broken Windows” theory to my own life and work as a CEO:

• Have a clean inbox at the end of the day. This also comes from David Allen's theory of workplace productivity and it works. A clean mind is free to think, dream and solve problems. The quickest path to keeping it clean is not having a pile of little things to deal with in front of it, taking up space.
• Show up on time. It may sound dumb but people who are chronically late to meetings are chronically behind. The day is spent rushing around, cutting conversations short—in other words, unhappy and unproductive. The discipline of ending meetings on time with enough buffer to travel so you can start it on time—and not waste the time of the other people in the meeting—is important.
• Dress for success. We live in a casual world, especially in our industry. Sure, I sometimes wear jeans or a Hawaiian shirt to work—even shorts if it's a particularly hot day. No matter what I wear, I make sure to look neat and professional, not sloppy. The discipline of “dressing up” carries productivity a long way. Want to really test this out at the edges? Try wearing a suit or tie or dress shoes that click when you walk one day to work. You feel different and you sound different.
• Follow rules of spelling, grammar, and punctuation. Writing, whether for external or internal consumption, is still writing. I'm not sure when everyone became e. e. cummings and decided that it's okay to forget the basic rules of spelling, grammar, and punctuation. Make sure your emails and even your instant messages follow the rules. You look smarter when you do. Maybe—maybe—go with abbreviations on Twitter or SMS. I wouldn't normally consider a lot of those formal business communications.

I could go on and on but I think you get the idea. A little self-discipline goes a long way at work—and in life!

Out and About

Besides working on self-discipline, I also try to keep mentally fresh by exercising my work brain in nonwork ways. Let me give you a couple of examples of that.

First, I like to spend time mentoring other entrepreneurs. I do this occasionally in formal ways via programs like TechStars or SeedCamp but I've done this informally for probably a dozen different entrepreneurs over the years. Even the occasional networking breakfast with a new CEO who knows people in common with me counts. While I hope my time spent with other entrepreneurs is useful for them, they're also useful for me. They help me generate good, specific ideas for my own business. I think I come away from every single meeting I have with any entrepreneur with at least one new to do for myself and my team at Return Path. There's nothing quite like seeing how another company or entrepreneur operates to spur on good thinking. Second, these meetings help me to crystallize my own thoughts and ideas. Much like writing my blog and this book, problem/solution sessions with other entrepreneurs force me to condense a cloud of ideas down to a simple sentence or paragraph.

Second, I try to focus my extracurricular time on helping organizations with the challenges that I'm most used to working in and around professionally. Earlier in my career, that meant I was helping organizations understand and use technology or online marketing and communication more effectively. One of these organizations was the golf course where I play and the other was my cousins' new wine store. Through both experiences, I had to define business requirements, work with vendors from selection through contract and then work with the vendor and the organization on deployment and process change. Both bits of work were directly useful for me to take lessons back and apply them to our processes and work with clients at Return Path, because I was suddenly The Client as opposed to my usual role as The Vendor. The learnings from the other side of the table are incredibly valuable and kept me mentally fresh.

STAYING HEALTHY

I had breakfast with a relatively new CEO the other day who said one of the things he was struggling with was being tired and feeling overworked. I told him that one of the things I make sure I do, come hell or high water, is to exercise at least three times per week and usually four or five times. He said he used to be a serious athlete but that he had stopped exercising when he started the business and asked me how I could afford those three hours per week to exercise. I asked him how he could afford not to spend that time!

There's a virtual cycle that comes from being in shape. You have more energy. You think more clearly. You eat more healthfully and drink less. You sleep much better at night. Of course, the opposite is also true: there's a vicious circle of being out of shape. You don't sleep as well, so you are more dependent on caffeine. You're not as focused during the workday. You probably eat and drink more, later at night. All of which leads to not sleeping well another night—and then the cycle repeats.

I try to think of the three hours of exercise every week as an investment in my own productivity. Here's my quick and dirty math on my “investment” of three hours per week of working out:

• Minutes spent exercising: 180.
• Work minutes during the week, assuming a 60-hour week: 3,600.
• Loss factor: 15 percent for travel time and other structurally nonproductive time.
• Net number of work minutes during the week: 3,060.
• Required productivity improvement to “balance” the 180 minutes of exercise: 6 percent.

Is there anyone out there that doesn't think you're 6 percent more productive when you're in shape? I'm not even factoring in the side benefit of (most likely) waking up earlier in the morning and getting a jump on your day as part of regular exercise. Or the fact that people who exercise need less sleep.

All that said, regular exercise doesn't just impact your productivity and give you more energy; it helps keep you healthy. Obviously, there is more to staying healthy than just exercise but it's a good start!

ME TIME

Exercise is a perfect segue to “me time”: time that you're not spending working or actively thinking about work. It's impossible to not have work running in the background at some level. My concept of “me time” has been pretty straightforward over the years, though it has gotten more difficult, along with the rest of my time management, as my company and my family have gotten larger. These things aren't necessarily right for everyone but I do my best to:

• Keep weekends to myself and my family (with at least a few minutes exclusively for myself). That doesn't mean I never, ever do any work on weekends. Most weekends, most of the time, I either don't do any work or I don't do more than an hour or two, from home, usually just sneaking in an occasional look at email. This does mean that I probably work more hours during the week than most people but I'd rather do that and maintain a little bit of down time on the weekend.
• Take at least one and preferably two, one- to two-week vacations per year where I completely unplug. I was much better about this before we had kids (vacations aren't necessarily the most restful times anymore), though I am seeing promising signs that we will reverse course on this front as the kids get older. Even in the early years of the business—those years where I felt like I could and should work every spare moment—Mariquita and I did one major, international, two-week, fully unplugged vacation each year. No email. No calls. Sometimes not even a cell phone. I gave my team my itinerary and told them how to find me in case the building burned down.
• Take a weekend or two each year to hang out with friends. Mariquita and I have a standing deal: each of us is entitled to a couple of weekends away with friends each year where the other one covers the home front. Although this has gotten harder to schedule over the years (and not everyone has a deal like this with his or her spouse!), the occasional golf or ski boys' weekend has been incredibly fun and refreshing.
• Use most of my train commute time and some of my airplane time, for personal reading. I can never quite manage to use all of it for myself but I use at least half—that's enough to keep me reading a couple dozen nonbusiness books per year and The Economist every week.
• Foster an outside interest or two. Kevin Ryan, a multiple time CEO in the New York tech industry, has a great saying: “You can do anything you want but you can't do everything you want.” It's so true. You can and should make time to do a couple of things outside of work that are most important to you, from spending time with your kids coaching a team or leading a scout troop to playing an instrument or taking cooking lessons. I also think that, for most CEOs, there is an element of goal-setting that can come along with this—usually, strong leaders drive themselves by setting large goals in their personal as well as their professional lives. Many (myself included) have set goals to complete marathons or triathlons or even (myself definitely not included) Ironman races. The goal doesn't have to be a physical one, either.
• Learn to say no once in a while. Any time I think about the topic of staying fresh and my ability to stop working once in a while, I come back to the my friend Seth's French Fry Theory of being a CEO. The theory is simple: “You always have room for one more fry.” It's pretty spot-on, if you think about it. Fries are so tasty and so relatively small (most of the time), that it's easy to just keep eating—and eating and eating—them, one at a time. You're never too full for one more fry. You might not order another plate of them but one more? No problem. Ever. I've always thought that the French Fry Theory can be applied to many things, including other food items. It definitely applies to being a CEO.

As a CEO, you can always do one more thing. Send one more email. Read one more document. Sometimes you just need to draw the line, go home and stop working! The world we operate in is so dynamic that it's nearly impossible to ever feel like you're completely on top of your job. There's always more to be done and the trick to doing it well is knowing when to say “no” and take time for yourself.