How to build a useful five-year plan

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Go out and dent the universe. Erin's parents didn't put pressure on her to get perfect grades or go to Harvard; they wanted her to use her privilege and beautiful upbringing to make the world a better place.

Youngest child syndrome makes you quick. Being the youngest of six, Erin learned to speak very quickly to get her thoughts in at the dinner table, and she was given unsolicited advice her whole childhood (which is why she loves giving advice now).

Your siblings' sole job is to keep you grounded. Erin's parents are proud and supportive, but her siblings roast her and beat her down (all in good fun) to keep her as humble as possible.

Success is attributed to a sense of humor. Erin gave career advice that was funny, and nobody had ever really seen that before. You don't get that unless you're the slightly bullied youngest of six kids your entire life.

Rejection rage is a choice. At a Women in Film networking event, the head of the organization paused Erin's documentary trailer 30 seconds in and said, "You need to be more realistic." Erin went on to get a Pulitzer fellowship and premiered a feature documentary at 23 with international distribution. When you get a rejection, you can either let it beat you down or say, "I'm going to show them."

"Tell me about yourself" is the world's worst interview question. It's lazy, not specific, and hard for the interviewee to truncate their entire life into 90 seconds. Use the past-present-future template: 1-2 sentences about your past, 1-2 about your present role, then future (where the interviewer's ears perk up), connecting to why you're applying for this specific role.

Specificity is the magic word. When sending cold emails, the chances of getting a good response dramatically increase if you're specific: specific praise, specific question. Instead of "Can I pick your brain over coffee?" say, "I watched your video about X, and when you said Y, it piqued my curiosity." Higher quality questions get higher quality answers. This isn't just for podcasts or job interviews; it's a life skill.

Good professional communication is like chess, not checkers. Most people just play checkers (you said this to me, I'm going to say this to you), but chess is thinking 10 steps ahead about what your end goal is and how this person falls along the path to that goal.

Don't ask for a raise; ask for an adjustment to your compensation. Your job is transactional (you do work, they pay you). When you accepted your salary, you were doing X, Y, Z. Now you're doing X, Y, Z plus A, B, C. It's no longer an equal partnership, so you need an adjustment. It's not personal, it's just professional. Know your audience and your leverage.

Emotional regulation is powerful communication. If we just act impulsively and say what's on our mind all the time, it doesn't actually get you where you want to go.

Always keep your desired outcome in mind. It's about checkmate. Don't just react, think about what the end goal is and how this conversation gets you there.

Humanize people, don't make them wrong. That egotistical senior VP is probably actually really insecure about where they are in their career and wakes up every morning not knowing what they're doing.

Put your ego to the side. Being a great communicator requires taking a break from thinking about yourself and thinking about what the other person's life is like and what their goals are.

Align your goals with their goals. Think about how you can create that authentic relationship by figuring out how your goals align with what they're trying to accomplish.

Shut up and listen. We do a little bit too much talking when we're trying to negotiate or strategize. It can be very beneficial to embrace the silence and practice active listening.

Curiosity is an amazing way to show love. Being genuinely curious about a person makes them like you, and it becomes more natural the more you do it.

Compliments have to be genuine and specific. People are way better at sniffing out fake compliments than you realize. If you can't find one thing you truly admire about someone, don't say anything.

Don't make it transactional. When people ask, "How do I not make it feel like I'm using them?" Erin says, "Well, don't use them. Just be genuine."

The most loving thing you can do is respect people's time. Meeting bloat has gotten really bad since the pandemic, and a lot of time is disrespected in meetings across the world.

Maybe don't have the meeting. A lot of meetings are completely unnecessary, or at least the way they're set up, the people invited, or the way they're run are really inefficient.

Only invite crucial people. Make sure that only the people who absolutely need to be there are invited to the meeting.

Always have an agenda. At the beginning of every meeting, say "Here are the three things we're going to cover today, and here's the goal of this meeting." Put it in the calendar link with bullet points.

Don't have brainstorming meetings. Have meetings with very tangible goals at the end, state them up front, and make sure that goal has been achieved by the end.

Email subject lines are underutilized. Erin's dad's company would put tags like "request," "informational," or "command" on subject lines so you knew exactly what type of email it was and what was expected.

The exercise of making a five-year plan changes your brain. Erin doesn't believe in sticking to a five-year plan, but the exercise of thinking about the future creates new neural pathways that change the way you think about yourself and your life.

A happy life is an intentional life. The vast majority of people float through life and act very reactionary. Sitting down and thinking about what you actually want in five years is powerful self-care.

Sit down with your partner and do this together. Before you get married, make five-year plans together. They might look really different (which is revealing) or really similar which doubles down on alignment.

Create multiple five-year plans if you're young. If you don't know which path you're going to take, create five different scenarios for yourself and see which one energizes you most.

Financial freedom is a goal worth stating. Erin wants to be financially free in the next five years, which allows her to pursue mission-driven work on her own terms.

You're just another human trying to figure it out. Even though Erin wrote the book on workplace communication, she's still winging it every day just like everybody else.

Combat the knowledge curse by staying connected to real people. When you're an expert in something, it's hard to imagine not being an expert. Erin moved back to Maryland suburbs to experience people working normal corporate jobs, DMs with people daily about their experiences, and gets on free calls just to listen. The data in newsletters tells a different story than people's actual experiences, so she stays grounded by hearing real anecdotes from IT workers in North Carolina or nurses in Kentucky.

Set goals really high. Erin wants her startup to help 500,000 job seekers in a year, which is ambitious, but she doesn't care if she fails as long as she tries to reach it.

More Learning

#507 - Jesse Cole: How to Build Your Idea Muscle

#344 - Jesse Cole: How to Create "You Wouldn't Believe" Moments

#365 - James Altucher: How to Become An Idea Machine

Reflection Questions

1. Good communication is chess, not checkers. Think about a difficult conversation you need to have this week. Instead of just reacting to what they say, what's your desired outcome? What would "checkmate" look like, and how can you think 10 steps ahead to get there?
2. Who in your life keeps you humble If no one does, how might you be losing perspective on yourself? What would it look like to invite that kind of honest feedback into your life?
3. Erin recommends making a five-year plan, not to stick to it, but because the exercise creates new neural pathways. When's the last time you sat down and intentionally thought about what you want your life to look like in five years? What's stopping you from doing that this week?