What Would Tim Ferriss Do?

September 23, 2016, 12:00 PM UTC
Courtesy of Tim Ferriss

A lot of people listen to Tim Ferriss. The best-selling author’s popular podcast has been downloaded more than 80 million times, earning him the nickname “the Oprah of audio.” Luckily, the self-help guru—and No. 28 on Fortune‘s 40 Under 40 list—has a lot to say. Ferriss, 38, has helped drive sales of books and toothpaste and other goods just by mentioning them on his podcast. But he is also looked to for guidance on time management and health and just about everything else in life.

We caught up with the author (and angel investor and Chinese kickboxing champion) to find out what he would do in a variety of less-than-ideal scenarios. Here’s what he said.

Problem: It’s that time of year again—performance reviews. You hate giving them (and getting them). What is a viable alternative?

I think that peer reviews are generally more valuable than top-down manager reviews. So I think you can offload a lot by having peers contribute. And the process shouldn’t be onerous if you do what I do with my employees: set very clear objectives up until that timeline. That way you have a very clear report card related to those key objectives that your direct reports agreed to take on and you shouldn’t have to do a huge mess of retrospective review. That should be something you track on a very consistent basis with clear milestones and timelines. The same way I would use a glucose monitor, I would try to assess employees consistently. Also, your memory is faulty, so you don’t want to rely on memory to assess performance.

Related: Check out Fortune’s full 40 Under 40 list

Problem: Let’s say you have a newborn baby. Both you and your partner are back at work and the baby is keeping you up at night. Do you take turns? Deal with it? Or is this the kind of thing you should outsource?

I don’t have a kid so this is a bit outside of my domain, but based on watching several of my high- achieving friends do this [have a kid] I would say a night nurse is by far and way the consensus winner, including among parents who were very averse to this. They just decided that getting sleep allowed them to be more present parents for the rest of the time they were with their child.

Problem: You are a startup entrepreneur who is also writing a book and also taking culinary classes and also training for the dressage competition in the 2020 Tokyo Olympics. You love all of these things. How do you go about deciding what to let go of?

The first thing, which I heard from Maria Popova [a writer Ferriss recently interviewed on his show], is that guilt and prestige are both bad reasons to do things. Am I a startup entrepreneur because I think that’s what I should like doing? What am I doing out of guilt or prestige?

The second—or maybe this should be first—I want to eliminate as many options as possible before trying to rank-order them. I think a common mistake is people try to put these things in a ranked order before disqualifying some of them. If it’s not a “hell f***ing yes” it’s a “no.” Don’t do something because it’s kind of cool. It’s very binary. This is how you can eliminate the middle. The middle is where I get lost.

For example, everyone wants to negotiate. You end up with long, protracted conversations. One of my friends recommended to me that I just do free or full retail [for speaking engagements]. Free speaking is for groups you really deeply care about or just get really excited about. Or, you just do full retail: ‘This is my price, if you can’t do it, no problem, I can suggest some other people.’ No negotiations. What happens with that? You lose a lot of deals, and that’s ideal. You end up only interacting with people who very specifically want to work with you. And, you end up getting paid infinitely more per hour.

Also, this is super important: The perception of me is different than the reality. Because different projects and activities sometimes get announced at times that they’re not actually happening it creates the illusion that I’m doing a thousand things at once. But I focus on single-tasking.

People always ask me what they can do to write a best-seller. Before we get to the best-seller part, the question I always ask is: Can this be your No. 1 priority for the next year, minimum? If the answer is no, I say don’t do it. It’s going to be a mediocre book, which is more of a liability. Same goes for startups. My point is that if you’re choosing to play in the winner-takes-all, venture-backed startup business and you have seven different side gigs, you are going to get your f***ing face ripped off. You are stepping into a zero-sum game against the most ruthless, high-energy 20-somethings. It’s a professional sport. You don’t see a lot of startup founders living off of ramen and Red Bull at age 40. If I can’t be number one in some category, I generally don’t play.

Problem: You have learned to say no to everyone but your mother. Seriously, you just can’t say no to your mother without feeling guilty. Any tips?

I have a personal experience with this—not with my mom but with very close friends and family. I recommend a book to a lot of people: The Drama of the Gifted Child. It talks about a lot of related topics. The second thing I say is that your success can be measured by the number of uncomfortable conversations you’re willing to have. This is a very big problem for a lot of people. They can’t have the most important conversations with the most important people in their life. What I would do is some version of calling your mom or meeting her in person and talking about whatever. Be super positive. Then bring up the serious stuff:

“Mom, I love you so much, I really value our relationship. I’m actually going to be putting time in the calendar so that I call you at least once a week. And I’d like to ask you to make a very proactive effort to become more aware of not using guilt as a weapon with me. It makes me feel terrible and makes me not want to spend time with you.”

You put it on the calendar. Then you take the reactivity out of it. I hate to be hardass about it. But if you can’t have a hard conversation with your mom, you’re f***ed. Unfortunately there’s no app for this, something where you just push a button and it takes the guilt away.