Think long-term: The Hello Monday Master Class brings you

💡 Take our listener survey & help us make a better show!

🎓 The Hello Monday Master Class!

We've distilled the essence of hundreds of conversations into five essential rules that will empower you to thrive in an ever-changing professional landscape. From knowing when to quit to navigating uncertainty to asking for more, this series is your guide to excellence. Tune in each Thursday through the end of June for actionable insights and collaborative exercises to elevate your career! Then, join us in the Hello Monday Group to complete an exercise together and connect.

5️⃣ Lesson Five: THINK LONG-TERM

Dorie Clark: A lot of the busy-ness we all face is self-imposed, it's chosen in some ways, because. For many of us, there are things we don't really want to face uncomfortable questions about whether we are doing the right thing or just not knowing what the right thing is to do. And it's a lot easier to just keep doing what you're already doing rather than take the time to dig into that and interrogate it.

That’s my friend Dorie Clark. She’s describing a sort of fundamental state of our always-on hyper-connected existence. We can always be doing something, we can always make ourselves so busy that we don’t have time to even consider, let alone plan for, really big goals. 

But when that’s the case, what do we really accomplish?

Our busyness becomes a sort of defense. It keeps us from realizing what is truly possible for any of us. 

Most of the things that are gonna matter to us in life will not come as a result of being busy, of filling our days with tasks. Our most significant accomplishments well, they’ll take thought and planning. Patience. Foresight. 

So today let’s consider what it means to THINK LONG TERM.

From LinkedIn News, this is Jessi Hempel, stick around for the Hello Monday Master Class.

Hello Monday is our show about the changing nature of work, yes, but even more than that, we focus on how we must CHANGE to be prepared for this future.

There’s a particular story I want to share with you today. It comes from Dorie’s own experience. She’s an author and a professor. And she’s building a new career for herself as well and that’s what we’re gonna into, actually.

A few years ago, Dorie wrote this book called The Long Game: How to be a long-term thinker in a short-term world. 

Most everything around us pushes us toward short-term thinking, small goals. Get to Inbox Zero. Land that promotion within two years. Finish the project. Answer your Slack. 

When we approach things this way, we only ever tackle things we KNOW we can do. Bill Gates often gets credit for saying that “most people overestimate what they can do in one year and they underestimate what they can do in ten years.”  

So how might you spend your time if you were focused on what you’ll accomplish in the next decade rather than next week?

Now, I fully acknowledge this can be a scary question in itself, because maybe you don’t have an automatic burning passion big goal. Maybe you don’t know what you want to do in the next 10 years. Dorie has something to say about that. Here she is.

DORIE: So one of the concepts that I talk about in the long game is really sort of pushing at one of the things we often hear that people sort of throw off as a bromide sometimes about “follow your passion.” And I get so troubled by this, not because following your passion is bad. I don't think it is if you're passionate about something, mazal but the problem that I see with so many friends that I know in so many, so many people who are very successful, is that oftentimes they have thrown themselves so much into their careers, that they might hit a point where they say, okay, the thing I'm doing right now, it's not, I know it's not quite right. I'm not quite happy. I feel stuck. I feel stagnant and they don't know what the other thing is. And you say, well, what are you passionate about?

They're like, I don't freaking know I've been working 70 hours a week and then they feel terrible. They feel ashamed. They feel like this monochromatic, boring person. And I just want to say it's okay. We don't have to bang our head against a wall and not do anything until we find our passion. What I suggest instead is a  framework is what I call optimize for interesting, because the truth is we might not know what passionate about. Like what is your soulmate career? But everybody knows at a really basic level, if something's interesting to them, like is math interesting? Is wine interesting? Do you like travel? Do you like music? What is interesting to you? And just do a little bit more toward that. Move in that direction, have conversations, learn something, read a book, talk to a friend who's in that industry, whatever it is.

I’ve learned a lot from watching Dorie set audacious goals for herself. 

And there’s this one goal she has that we’ve actually talked about a good deal. Back in 2016, which kind of feels like a long time ago now, a friend took Dorie to see the musical Fun Home on Broadway. Do you know that show? It was so fun. And everybody thought it was great, not just me, I mean it won five Tonys. It was an adaptation of Alison Bechdel’s graphic novel about coming out. The music was incredible. 

Dorie had never been to a Broadway musical before, it was her first, and she woke up the next morning after seeing it, and she was completely inspired.

DORIE: I was just possessed with this feeling, this certainty like, I need to write a musical. I need to learn how to do this. And so I just began going with it. I feel like whenever you get a very strong sense of something, especially something that doesn't make sense, frankly. That is a sign you should follow it. Because otherwise, like where would that be coming you know, to me, it was just like, oh, this is a direction that apparently I should follow and something that I am a strong believer in. And this is, really where, to me, long-term thinking and playing the long game differs from, let's make a Pinterest board and read the secret. Right? I am, I am not a fan of, wishful thinking and like, oh, manifest it. I am a fan of coming up with big ambitious goals, but planning for it.

So I actually went and had coffee with a woman once. And she was this sort of big, like magical thinker. And she’s like I have a vision. I have a plan. I am going to have a show on Broadway this fall. I was like, uh, have you been off-Broadway? Tell me what is the rationale for this goal? Like, I don't want to crush anyone’s dreams. But you know, pre COVID, this was not in the least rational. If you know anything about how Broadway works, there are 41 theaters period that make up Broadway at any given time. 20 of them plus are occupied by long term, shows like The Lion King. They're not opening up.

It is such a narrow band that you need to either have a major producer behind you or millions of dollars in backing. Otherwise, literally no way. So she just sounded like she was on crack, you know, but instead, what I realized is for me having a 10 year vision of getting Broadway, I didn't necessarily know how to do it. I didn't know what precise steps were, but I knew that it was rational that if I were to work assiduously on a 10 year timeline, it actually could be practical. 

By the time Dorie came into the studio, she’d already been working toward this goal for five years.

And I have now, learned how to write musicals. I've been accepted to and completed one of the country's most prestigious training programs in musical theater, you know, finished this show that I'm now shopping around and trying to market to people and have built relationships over the past five years with several dozen producers. So I don't know if I'm going to get to Broadway by 2026, but it is not impossible.

And part of the reason is that think we really need to do a better job of scoping out our ambitions to begin with. There's a story that I tell in The Long Game about Jeff Bezos and a 2018 letter to shareholders that he wrote, where he talks about a friend of his, that hired a handstand coach to get better at handstands in yoga.

And the handstand coach says the average person thinks it takes about two weeks to be able to master a handstand. It actually takes six months. Of daily practice. I mean, it's a 12x differential. And so ultimately, you know, no wonder people give up after two or three months, they say, oh, well, I couldn't possibly do it. It's me. It didn't work. It's not you. It’s that literally people can't do it that fast. And so understanding the scope of what something takes upfront is so essential because it enables you to make rational plans so that you actually can accomplish the right things.

One of the biggest reasons that I have sometimes failed to name these big swings for myself is because I don’t know HOW to accomplish them and so I don’t trust that I will. I’m afraid that I’ll fail. And I’d rather not try, than to try and to fail.

I asked Dorie about this. I mean there she was telling me about some goal that seemed pretty ludicrous on its face, and she was still working out the specifics of how she’d do it. What if, after writing about it in her book, after telling me about it in the studio, what if it didn’t work? What if she didn't actually get a show on Broadway? 

DORIE: I'm actually not too troubled about that possibility. I mean, you're exactly right. I put it out there in midstream. This is not a fait accompli people can watch along and see, oh, was she able to pull it off? But I have a genuine faith in my abilities to pull something off. And here's why: number one, I think a lot of people get hung up on things like imposter syndrome, you know?

There shows that I have seen on Broadway that I am like, whoa, I could for sure write something better than that. I know I'm good enough to be on Broadway because a hundred percent, it is better than that. And so I feel totally confident in that way. It's really just a question of networking and working my angles until I get it on Broadway. Now, another point that I make in the long game is talking about multiple paths to your destination. And so this is the key, right? If Netflix comes in and Netflix is like Dory, forget Broadway. WE want your sexy lesbian spy, thriller musical. I'm not going to say no! 

JESSI: I'll produce that.

DORIE: Incredible.

Well, you know, we'll talk, we'll talk afterwards, but you know, it doesn't necessarily have to be Broadway. I'm open to a better offer if one emerges. And I think that sometimes we get so hung up. Oh, I have to get the job at Google. Oh, I have to get into grad school at Penn or whatever. There's a lot of routes that you can take to get to the same place that you want. That's directionally correct. And that's what I'm aiming for.

That is a pragmatic kind of confidence, one we’d all do well to embrace.

So here it is now, 2024. We’re 8 years into Dorie’s ten-year challenge. Dorie and I got together recently with some friends for dinner, and I asked her how it was going.  Well, I'm here to tell you it's going great.

She has three projects in development right now—including that lesbian spy thriller. She's pretty sure she'll be able to pull it off, to have something on Broadway in two years, and believe you me when I say, we will definitely check in with her.

➡️ Our final challenge: A Big Goal

So now this question is for you: what’s your equivalent to the theater-writing goal? What is something that feels so significant that it would be worthy of a decade of your attention? I mean, if when you're thinking about it, you don't feel a little quiver in your heart, a little fear, you're probably not thinking big enough.

For this week’s challenge, you may want to go back and relisten to the Dream Job episode from the start of the year. I'll drop it in the show notes. Your goal is truly to think of something so significant you don’t feel at all sure that it can happen.

And then when you have it, I’ll start a post as I’ve been doing for the last month in the Hello Monday Group on LinkedIn. Our fifth and final master class challenge. Please jump in and add your goal to the comments. And while you’re there, check out the goals around you and let’s cheer for the people who are choosing to drop them. That’s it for this week’s master class and for the series as a whole. I’ll put links to the full episodes in our show notes.

Hello Monday is LinkedIn News’ weekly podcast about the changing nature of work—and how we must change to keep up. It's hosted by me, Jessi Hempel. Subscribe to the show's newsletter.

Follow us: Apple Podcasts | Spotify