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🎥 Goals Are Guesses with Carl Richards → [WATCH LINK]
Prefer to read? The edited transcript appears below.
What we cover in Episode 4 (Goals Are Guesses)
In this episode, I sit down with Carl Richards—a certified financial planner, author, and creator of The Sketch Guy column in The New York Times. Carl is known for his simple yet powerful sketches that make financial concepts easy to understand, as well as his best-selling book The Behavior Gap.
Pressure around goal setting keeps many people stuck. In this discussion, we reframe goals as guesses—temporary best ideas based on who you are today. Pick a direction aligned with your values, reduce the step size, and measure progress by learning and alignment, rather than perfection.
Key ideas
- Permission to evolve: Today’s “goal” is a hypothesis, not a verdict.
- Smaller steps, faster learning: Reduce scope to reduce pressure.
- Alignment over achievement: Track whether choices fit your values.
| One Small Step (this week)
Run a 7-day “guess → test → learn” loop 1. Write one guess (e.g., “A weekly money check-in will lower stress”). 2. Pick a tiny step (15 minutes, once). 3. After 7 days, record what you learned and your next tweak (keep, adjust, or drop it). |
Phil Weiss
I’d like to revisit the word goals because you have a sketch called ‘Goals or Guesses.’ And I know I agree with the concept. I’ve also written a blog on that topic. I’d love to hear you discuss the idea of reframing goals as evolving possibilities.
Carl Richards
Yeah, I love that. Possibilities are really nice. What I’m trying to point out is that the word goal has become so loaded. There’s that Harvard study. I know I should have goals. It turns out the Harvard study didn’t even exist, which is really funny. But I know I should have goals. All smart people, all successful people have goals. But I’ve noticed over the last 25 years of asking clients that, literally, maybe the first question back in the old days could have been, ‘What are your goals?’ Anytime you ask, I mean, I’d ask your listeners to just think about how it feels when they’re asked, ‘What are your goals?’ And I feel it. The base of my, like between my shoulder blades at the base of my neck and a little bit of my chest; sort of like pressure and tension. And there’s also this sense of I have to get it right. And the goals or guesses is just an effort to make it more playful. We don’t really know anyway. All goals are just guesses. Like some of them, sometimes we have to convince ourselves that they’re really, really important. And sometimes we call them strong opinions loosely held. But one-half of our brain can’t know about the loosely held part. Because we have to be so focused on meeting the goals. But in the back of our mind, we’re like, hey, by the way, you’re allowed to change them. And so that’s all I’m saying. Let’s make it a little more playful, shall we? Goals are just, they’re just a guess. Relax. Guess for me. Like, what do you think you’d like to be doing in 10 years? Okay, cool. And then that acts as a sort of stake in the ground. We can kind of head that direction. Because I promise you, we’ll get new information tomorrow, next week, or next year, and you’ll be like, ‘ You know what? ‘ I thought I’d really like sailing. I went sailing. I don’t like it. Right? Like that’s just meant to be a suggestion to the mind to relax a bit.
Phil Weiss
When you say that, it reminds me of when you had Gretchen Rubin on your 50 Fires Podcast, and she told a story about skiing.
Carl Richards
It’s so good. Yes, let me just recap it quickly for your listeners. [You can listen to the podcast episode here.] She [Gretchen] was at a cocktail party, a dinner party, something, and they had either just come or they were just headed to, I can’t remember. Can you remember?
Phil Weiss
They were heading.
Carl Richards
Yeah, I think they were just headed out to Colorado, or yeah, probably Colorado, not Utah, because the skiing is terrible in Utah. Don’t come to Utah. It’s just sort of a joke. [Carl lives in Utah and skis there frequently.] But they were headed to Colorado, and somebody else, she mentioned that to somebody at the party, and the other person was like, ‘Oh, do you ski?’ And Gretch was like, ‘No.’ And she’s pretty sure of it, right? Like, no, we don’t ski. My husband and I have decided that we don’t enjoy skiing. We just like going to the mountains in the winter. And the other person was like, ‘You’ve got to ski. You’ve got to. It is so fun, and she took like a few minutes to try and convince her about skiing. Gretchen was like, ‘No, we don’t ski.’ And the lady left. She came back 15, 20 minutes later or something and said, ‘You know what? I don’t like skiing either. You know, I have just been doing it because that’s what you do. And I think it’s so, that was such a great story. I mean, kudos to both of them, right? Especially the lady who came back. I mean, I love that Gretchen was so sure of just, no, we don’t like it. Thank you for the suggestion. But I love that the lady came back and was like. Wait. And I think what we’re saying by ‘goals equals guesses’ is that we’re giving you permission to be okay with realizing, ‘Wait, that’s just something my dad told me to do.’ Or this is my sister-in-law’s goal. Or I read about it on Instagram. I don’t even like it. I don’t even like it. We had recently realized that this also applies to friendships. It’s okay for you to wake up one day and realize that you don’t really enjoy spending time with that person. Right? And it turns out they probably might not even enjoy spending time with you either. It’s okay to make changes and evolve and change. So goals equal guesses. Goals equal guesses.
Phil Weiss
I love that. I love that. And as you’re saying it, I’m thinking about one of the things I’ve told my kids: If I look at my career and this really applies, is the idea that you don’t want to go through life with these blinders on. You don’t want to just look down this narrow path because there may be something way out to the side that you’re only going to see because you didn’t have those blinders blocking your vision. When I look back at my career, I see that it has undergone numerous changes, and I’m finally doing the thing that I genuinely enjoy. However, it never would have happened if I had always followed a narrow pathway and believed there was only one way to go.
Carl Richards
Everything you’re saying, Phil, is really interesting. This whole conversation just reminds me of all the tension. And there’s an essay in the book called When Values Collide that I’m sort of really proud of just because it’s pointing to this idea, that there is a time to just lock the blinders on, right? Burn the ships, they say, like burn the boats. Get rid of all the options. And boy, stick your head up every once in a while and look around. And maybe there are whole chunks of your life. I would suggest that college is one of those chunks. Early dating is one of those areas where you should get as many variable reps as you can. Maybe the sport you want to participate in when you’re 10, 11, 12. I think some of the best parenting advice I ever got was, sign them up for lots of different things. Right? There are times when I think we’re intentionally exposed to a lot of things. Then there are other times when we want to lock down. You know, I love this. I’m going to lock down. Awesome. Then remember, it’s going to probably come up again. So, I love this tension between competing variables, competing values, you know, because the truth is, we’re not trying to resolve that tension. A rich life is made because of that tension with plenty of periods of rest, right? Yeah.
FAQ—Goals Are Guesses
1. If goals are guesses, how do I choose them?
Treat them as hypotheses or possibilities. Choose a direction that aligns with your values today, take a small step, and refine it based on feedback.
2. What if I pick the “wrong” goal?
No problem. Replace “right/wrong” with “learning/next step.” Adjust the guess; don’t abandon the process.
3. How do I reduce the pressure around goal setting?
Shorten the time horizon, shrink the step size, and measure progress by learning and alignment—not by perfection.
All Episodes
- Real Financial Planning (Ep1) → [EP1]
- Four Sources of Capital — TEAM (Ep2) → [EP2]
- A One-Page Plan (Ep3) → [EP3]
- Goals Are Guesses (You are here)
Next up: Tax Planning, Not Reporting (Ep 5)
Practical, forward-looking moves (within your broader plan) to avoid avoidable taxes.
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