The hard thing about realizing it’s a hard thing

If you haven’t already picked up Ben Horowitz’s book The Hard Thing About Hard Things, you should. When I started to read Ben’s book, I thought that I already knew many of the things he would share, and that the payoff of reading the book would be learning about his particular struggle and viewpoint on startups. I was wrong. Full stop. Reading this book made me realize that when you’re working on a hard thing there are no easy answers and that you have to do everything you can to solve them. I knew these problems are hard – I’ve worked in startups before – but this realization was different.

Doing everything to solve a problem also means you don’t have the ability to solve every problem all of the time. You don’t have the ability to spend all of your time at work. And you don’t have all of your time available to be with your family. And you certainly don’t have time to be alone in your head not thinking about the problem. What you do have is the ability to work on the most important thing possible and to keep asking yourself at different points in the day, “Am I working on what’s most important?” Ben’s point is that you have to be brutally honest with yourself to know what’s important.

The meaning of important will change throughout the hour, day, week, and month. And the insight I gained from Ben’s book is that the most important thing isn’t always evident – it’s a combination of what you feel in your gut and the data that you gather – and you need to try very hard to stay true to that instinct. You won’t always be right, and it’s in fact guaranteed that you will make some mistakes. So what should you do when you realize you’re working on something hard?

You need to keep your body and brain going. That means that you need to eat right, get at least some exercise, and figure out when you can get sleep. When you’re working on a hard problem you often need to put in extra hours. If you put in extra hours every night you’ll run out of gas before you solve the problem. I’m not sure what works for you, but it helps me if those aren’t consecutive late nights. And family time? Yes, that’s important too. Turn off your phone. Turn off your laptop. Try your darndest to make some of your time real family time (no, not multitasking time, but actual family time.)

There are only so many hours in a day. If you want to spend your time solving hard problems, you will have to give up some of those hours to solve the problems. Make the hours you spend count. You’ll only know how hard the the problem was when you look back and see how high you climbed.

There is always more work to do.

photo by

This post is part of the Startup Edition series on Enterpreneurship

What’s on your To-Do List?

Right now you have something else to do. Later today you will also have something else to do. And tomorrow you will have the opportunity to pick new things to do and catch up on the things you did not get done from today. There are also the other things in your life that need attention – they might be family time, your spouse or significant other, that run you are putting off, or any number of side projects and obligations – so how do you manage stress and life balance as an entrepreneur?

I start from routine. Knowing what I’m going to do in a day helps me to prepare for the uncertainty that will also happen. I make sure that I cover my bases – eating well, making sure that I sleep enough, and going home at the end of the day. Eating well often means explaining to people that I avoid gluten, dairy, and egg, and it also makes it hard to eat while I’m on the road or away from my house. Sleeping enough is challenging. You can always get more done late at night, and I’ve learned through experience that late night learning  is just not as effective as the benefit you get from sleep. And I go home. There’s a lot of pressure in any office to be the first one at work and the last one leaving. Even better is the feeling that you can go home and still know what you need to get done.

What can you get done today?

You also need to know (and be able to identify) Your Most Important items to be able to leave the office and still be productive. I do spend the time at home to get done whatever needs to get done, and I usually do that after my kids are in bed. Protecting family time is one of the best ways I know to reduce stress and feel like I have a more balanced life.

Except when your life isn’t so balanced. Because as an entrepreneur, there are often times when the business/problem/idea is all-consuming. If you have built up goodwill with your family and/or significant other to be able to ask for the time you need, you’ll feel better about being fully present in your startup – and being able to put your phone/computer/work brain in the other room during family time.

Balancing Stress is an Ongoing Challenge.

Is this a perfect system? Heck no. It’s a strategy to balance the stress of being in a startup and to maintain the smallest version of a big goal that I have: to be present for the people who matter to me, in the moment when we are present together. I’ve made the mistake in the past of trying to double, triple, and multi-task. It feels successful while you’re doing it, and results in action, but doesn’t identify, move forward, and solve the most important things you need to get done. So spend your time focusing on the biggest small thing you can get done. Eat well. Get enough sleep. Move around. And hang out with the people you love.

Managing stress and life balance as an entrepreneur means getting very comfortable with ambiguity. The sooner you internalize that and learn what you need to do to cope with that uncertainty, the better. The bad news is that there is always more work to do. The good news is that there is always more work to do. Get that work done on your terms and be able to tell a great story about it, and you’ll feel like you are managing your startup on your terms. Finally, Perfect is the Enemy of Done.

This post is part of the Startup Edition series on Enterpreneurship

Vacation is for catching soap bubbles

Soap bubbles are great
Catching a bubble

Time to Unplug

The best thing to do on vacation is – well, anything that you can’t do online – and you should take the time to unplug and recharge. Getting off of your normal routine can help you recognize the parts of that routine that you should keep (and perhaps the parts that you should think about leaving behind.)

A great place to explore

Whether your pastime is beach walking, finding a new restaurant to visit, or just reading a book, vacation is a great place to explore your ideas. Try some new things; try some old things; and just try something that you want to do (just for yourself.) You might find that some of these ideas are great. And you might find (like I did) that sometimes when you go to a new restaurant there is a boy at the next table who can’t hold his dinner and barfs all over the place. The point is that you never know what you’re gonna get. Sometimes it’s disgusting, and sometimes it’s beautiful.

Don’t Forget What You Have

Vacation is also a good time to take stock of the things you have, not just the things you want to try. It’s a lot easier to appreciate friends, family, your job, and other things when you’re out of your environment and in someone else’s space. And yes, I feel very fortunate. And I’m also going to continue working very hard when I get back (but not right now.)

Gone in an instant

The best parts of a vacation are like a soap bubble: beautiful, fragile, and gone in an instant. If you are paying attention, you’ll savor them while they’re there and maybe even catch a few photos to remember them by later. But the ideas don’t have to be gone in an instant – you can take them back with you to your work and to your regular life, so that part of your vacation and stick around – until the next one.

Starting a new job is never easy, so just jump in!

Diving Into And Out Of The Sky - Photo by

Tomorrow’s the beginning of a new chapter for me – I’m leaving Gist and joining Assistly. It’s been a great run and I am looking forward to staying in touch with my good friends and Gist and to gaining new friendships at Assistly (Seattle peeps – I’m not moving, and San Francisco peeps – I’m going to see you a lot more often ;).

There are a few key things I’ve noticed in this transition about starting a new job which could also apply nicely to most new things that you want to try, so here they are:

Act Like You’re Already Doing It.

Some might call this “fake it until you make it,” but I think the single most important thing you can do when you are starting a new opportunity is to act like you’re already doing it. For some jobs (like astronaut) this might be slightly impractical but for most folks there is ample opportunity to demonstrate both to yourself and to your new employer and co-workers that you are capable, willing, and eager to do the new job. (Who knows, you might learn some valuable skills as you’re doing it.)

Be Willing to Make Different Mistakes at Your New Job

If you’ve been in your current role for more than a year or two, you’ve probably made your fair share of mistakes (good! Hopefully you learned from them and they were the kind of mistakes that weren’t un-fixable.) So, when you move to your new role, if you’re willing to open yourself to the possibility that you will make new and different mistakes (probably also hoping to make fixable ones ;), you’ll probably learn more about your abilities and the new job while you’re at it.

Just Do It.

There’s no substitute for jumping in and doing the work. You can think about it all you want, but like the classic The Mythical Man-Month, throwing more preparation at your new job doesn’t guarantee success (if you’re an astronaut or if you work in an ISO9000 industry, it probably helps, but that’s a relatively small percentage of the working population.) Even if you have specialized skills that took you years to learn and perfect, using those skills in a new environment, with new co-workers and new customers is going to teach you some new things.

Keep Your Eyes Open

Pretty soon this will seem like “your job” again, so acknowledge that you are going through a special time where you have the opportunity to learn a lot and expand your brain (and don’t forget to have fun, too.) Victor Turner writes about the quality of being “liminal” and being not in one place or the other – this is the essence of the beginning of a new experience. So embrace it. I’m trying to do so this week, and in the coming months ahead.

Blog at

Up ↑

%d bloggers like this: