For Overwhelmed Founders, Less Is More

by Jason Shen, cofounder of Ridejoy and author of Winning Isn’t Normal

This is the second in a 6-part series on developing the habits that will make you a better startup founder. You may want to start with my first post: How to Use Structure to Become a More Effective Entrepreneur.

One of the reasons people cite for wanting to start their own company is control. No more stupid meetings. No more annoying coworkers. No more inane policies. Many first-time founders think that by starting their own company, they’ll be able to focus on what really matters.

Well, it turns out that’s not quite what happens.

Founder Overwhelm

Yes, as a founder, you have the power to hire, direct product, approve expenses, strike deals, and more. But you also now have tremendous responsibilities — especially once you have investors, customers or employees. In many ways, starting a company means giving up a fair bit of control over your day-to-day and week-to-week schedule. Things come up, and your priorities will adjust.

There will be days where you feel like you’ve been working hard and stayed busy all morning, noon and night, and yet when you look back on the day, you aren’t sure what you did exactly.

Even in the early days, though you might be spending a lot of time in the lab, the shop, or on your laptop, you still have a ton of decisions to make. Should you work on this cool new feature? Should you address the bugs that came up in the last round of testing? Should you scrap this whole thing and start on a new version?

So how do you deal?

Habit One of Effective Entrepreneurs

At the end of the day, grab a sticky, write down THREE (3) important (and finish-able) tasks for tomorrow, and post it on your keyboard. Read it again first thing in the morning, and commit to making significant progress on those tasks.

By committing to this habit, you ensure that you’re moving the ball forward on the most important parts of your business. Like finishing up that legal paperwork you’ve put off for weeks. Or tackling the backlog of customer support emails. Yes, crises will come up and you’ll have to deal with them.  But the true emergencies are rare. Most days you’ll get swamped by things that feel urgent but don’t matter. With Habit 1, you stay in control.

Now I know what you’re thinking: “Just three tasks? What kind of weak crap are we talking about?” Sure, three things might seem like not very much, but when you’ve got stuff coming at you from every direction, getting a specific, pre-determined set of three tasks completed will be a challenge. But it will be worth it.

The Most Effective “Productivity Porn”?

Marc Andreessen, cofounder of Netscape and cofounder of the widely respected VC firm Andreessen Horowitz, once documented several of his best productivity habits on his blog:

“I sit down at my desk before I go to sleep, pull up my To-do List (which I keep in Microsoft Word’s outline mode, due to long habit), and pick out the 3 to 5 things I am going to get done tomorrow. I write those things on a fresh 3×5 card, lay the card out with my car keys, and go to bed. Then, the next day, I try like hell to get just those things done. If I do, it was a successful day.

People who have tried lots of productivity porn techniques will tell you that this is one of the most successful techniques they have ever tried.”

Entrepreneurship is a contact sport. But that doesn’t mean you can brute force it. Every night, think hard about what matters for the business, and work like hell to accomplish it.

Jason Shen cofounded Ridejoy, a Y Combinator backed startup that helped tens of thousands of people share rides across the US and Canada. He is currently serving as a Presidential Innovation Fellow at the Smithsonian and writes on his blog, The Art of Ass-Kicking about startups and behavior change. He’s also the author of a new book, Winning Isn’t Normal.

One response to “For Overwhelmed Founders, Less Is More

  1. This is germane advice for all workers, not just founders. As cool and helpful as digital productivity apps are, a laundry list of tasks can lead to decision paralysis. When we have more things to do than time to do them, prioritization becomes the most important tactic.

    Fast Company published a great article called “The Amazing History of the To-Do List” yesterday. The article shares the story of how efficiency expert Ivy Lee transformed productivity at Bethlehem Steel.

    “Lee’s advice to each member of the company’s management team was to write a to-do list at the end of each day, which consisted of the six most important tasks to be done the following day. Then they were told to organize the list based on the highest priority tasks.”

    Good stuff Jason. Felt like I had to comment because I just wrote down my five things for the day.

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