What I learned about working from home

Working from home can be incredibly freeing if you otherwise work in an office year-round. But if you have a corporate job, how can you work from home without your boss or coworkers raising questions?

A few years ago, I was working long hours at a corporate job and I had a horribly long commute. At one point, I simply decided to take a day off in the middle of the week.

Instead of commuting twice and being in the office for ten hours, I simply grabbed a book and walked to a coffee shop.

It blew my mind how free I felt.

Here I was, when almost everyone I knew was at work, and I was enjoying a fantastic cup of coffee and a pastry while reading about the history of the Roman Empire. It helped that I was living in San Francisco, so that after reading for a while I could walk through a sunny city with beautiful parks.

Looking back now, this was a key moment. After I sampled this freedom, I knew I couldn’t stay in corporate for long.

I wanted to enjoy this freedom more often. But like most people, I didn’t have that many days off. So instead of taking days off, I started working from home or from a coffee shop now and then.

A day off brought the most freedom, but working from home I still felt so much more free than when I was at the office.

But you can’t just stop showing up at the office and expect everything to be okay. In fact, I quickly learned that there’s one thing you absolutely must do when you’re working from home:

Communicate, communicate, communicate.

When you work remotely, your coworkers and your boss don’t see you. Regardless of your productivity at home or in that coffee shop, some people might assume that when they don’t see you, you’re not working.

To avoid questions about your productivity, try emailing your team in the morning and tell them what you plan to work on. And at the end of the day, send an email with an update on the progress you made. (Or better yet, use a tool like Basecamp and post the updates there.)

Don’t expect people to assume that you’re working productively at home, or that you’re even working at all. Show them.

Even if your day was not very productive, just mention what you did do. It’s a lot better than staying quiet all day.

If you have a corporate job, I want you to be able to experience that same feeling of freedom that I did when I first started working from home. But if you work remotely, do it right by communicating more than you’re used to.


— Peter

How ambitious should your goals be?

For the past two days we’ve talked about goals. I suggested that while you can measure your productivity in many ways, the best way is to judge it by whether you’re achieving your goals.

Yesterday, someone asked: How do I know whether I’m setting goals that are “too easy”? What if I am capable of much more and I am holding myself back (by setting goals that are too easy)?

Good question.

Here’s the best way that I know of to determine whether your goals are too easy, too challenging, or just right:

First ask yourself how you want to feel after you reach your goal.

Let’s say you’re starting a side hustle and your goal is for it to generate $500 in passive income per month, six months from now. Ask yourself: why do you want your side hustle to generate $500 per month?

When you want something, you want it because it will make you feel a certain way. How do you think earning $500 per month in passive income will make you feel?

Do you expect it to make you feel proud? Accomplished? Do you have something to prove to someone, so are you expecting to feel vindicated if you reach your goal? Investigate your motivation.

Once you pinpoint how you want to feel, compare that with how you actually feel after achieving the goal. Do you feel the way you want to? If so, congratulations! You set a great goal and you met it.

But if you met your goal and you felt bored or disappointed, then set a more ambitious goal next time.

By contrast, if you met your goal but you felt incredibly stressed and were terribly cranky leading up the the goal’s deadline, then take your foot off the gas. Set an easier goal next time to avoid that stress, because excessive stress is super unhealthy.

(If you didn’t meet your goal at all—well, set an easier goal next time!)

There are other ways you could end up feeling too. When you figure out how achieving the goal made you feel, it will be obvious to you how to adjust your goal-setting for the future.


— Peter

P.S. Today I’m hosting my free webinar called Get Organized with OmniFocus. I hope to see you there!

A better way to measure your productivity

Yesterday we talked about a bunch of ways to measure how productive you are. What’s the best way?

My favorite measure of productivity is whether you achieve your goals.

In particular, it’s whether you achieve SMART goals.

SMART goals are partly objective and partly subjective. They’re objective because they’re measurable, but they’re subjective because you have to come up with goals that add something to your life.

If you achieve your goals, you’re productive, in the sense of putting in effort on the right things. If you don’t achieve your goals, you probably aren’t putting in effort on the right things.

This is not a perfect measure. You might hit a goal through sheer luck, or miss it as a result of something that’s outside of your control. But you can minimize that problem by setting goals that are related to your effort instead.

For example, one of my goals is to write to you every day for 365 days in a row. (So far, so good. 💪🏻) Each day that I write and publish, I am meeting my goal. I won’t “complete” or “achieve” the goal until some time in April 2019, but in the meantime I am productive every day that I write and publish.

Using the achievement of your goals to measure your productivity can also help you avoid feeling bad about taking breaks.

Let’s say you’ve worked lots of hours for two weeks. Now you’re really frazzled. What’s the most productive thing to do tomorrow: work lots more hours or have some downtime?

In this scenario you’re better off taking a break. But if you were measuring your productivity by “hours worked”, taking a break would count as not being productive.

(My favorite way to take a break is to spend a day at a wellness resort. It’s a great way to get away from your work and from your devices. Ever tried it?)

By contrast, if you measure your productivity by achieving your goals, taking a break is a productive thing to do, because it will refresh you and increase the odds that you’ll achieve your goal eventually.

How productive do you feel? Does that feeling change when you judge yourself by your achievement of your goals instead?


— Peter

What does productivity look like?

You want to be productive. I want to help you be productive. But what does “being productive” look like?

Here are some ways you could measure your productivity:

  • Hours worked
  • Revenue earned
  • Monthly salary
  • Promotions received
  • Number of proposals sent to clients
  • Number of meetings held
  • Lines of code written
  • Frequency of positive feedback from coworkers
  • Number of tasks checked off of your to-do lists
  • Number of projects completed
  • Number of words written
  • Lines of sheet music composed
  • Number of eggplants sold 🍆🍆🍆

Some of these might strike you as silly, but I can make a case for each of them.

If you’re a writer, the number of words you write matters. The quality of the words matters too, but many writers will tell you they’d prefer to write 1000 crappy words to writing zero good ones.

Number of meetings held? In some projects, a lack of regular meetings is a bottleneck. Yes, there are often alternatives to holding more meetings. But I can think of cases in which the number of meetings is a decent measure of productivity.

Still, some measures are better than others.

If you want to quantify your productivity, you have to pick a measurable quantity. What do you measure?


— Peter

A little less conversation, a little more action please?

Think about a project you aren’t making much progress on. Or a goal you’re not on your way to achieving. What’s stopping you?

To produce meaningful work, you usually need some combination of planning and doing. Planning helps you work efficiently on the right things and doing—well, that’s obvious.

So this project or goal. What’s preventing progress? Do you lack planning or do you lack doing?

(Or do you lack both? In this latter case, I encourage you to don your Sherlock Holmes hat and investigate your motivations. 🕵🏻‍♂️)

Someone who jumps right into things without a plan could invest lots of time and have little to show for it because she doesn’t have a solid strategy. She might haphazardly do tasks that don’t work together to complete the project or achieve the goal.

By contrast, someone who over-plans might spend dozens of hours consuming all the knowledge he can find on a specific topic. He might be keen to avoid beginners’ mistakes—a laudable tendency—but end up always wanting to learn just a little more before getting started.

When you think about your other projects and goals that have stalled, maybe you’ll identify a pattern. For example, I am a chronic over-planner. I have perfectionist tendencies and so I like to learn, learn, and learn some more to avoid making mistakes. Slowly, I am learning to do without excessive planning. I’ve discovered that it’s often more efficient for me to act without planning, make mistakes, and then to adjust.

Maybe you recognize yourself in this description. Maybe you are just the opposite. Or perhaps you can perfectly balance planning with doing, in which case: please share your secrets with the group!

So, are you biased towards action or towards planning?


— Peter

Taking pride in your work

Do you know that feeling when your boss tells you to do something quickly, at the expense of doing it well? Or not to do something that you think would be the right thing to do?

Put differently: when he and you have different standards.

I’m interested in finding out what makes people take pride in their work. Pride seems to be a sustainable emotion that consistently generates happiness.

And I think pride has a lot to do with your standards.

Maybe you can help me out by answering this: Do you take pride in your work, and why (not)?

If my hypothesis is correct, and pride is partly about meeting your standards—not someone else’s—then one obvious way to feel more pride in what you do is to be your own boss.

When you are your own boss and you want to offer “no questions asked” refunds, you can. As your own boss, if you don’t want to work with people with a certain personality type, then don’t.

But if you have that freedom, you still have to decide what standards to set. So, regardless of whether you have that freedom today, what standards would you set if you could?


— Peter