In short
How to stop doubt from stealing your dreams by combining “cringe-tolerance” with a practical planning/action system (“swimming with sharks”): schedule a recurring “breaststroke meeting” to plan and research, then act (“crawl”) immediately after.
Guest background
Hampus Jakobsson, an investor for ~20 years focused on people building the future; previously scaled his first two companies globally for ~10 years. He interviews star chefs, celebrities, athletes, performers, and CEOs to study what they were like before fame.
Key claims
Extraordinary people handle cringe; doubt “gets an appointment” but shouldn’t control you; success requires both direction (breaststroke) and momentum (crawl).
Notable examples
Ann Daniels, a single mother of triplets with panic attacks who joined an all-women North Pole expedition after seeing an ad, survived early selection challenges in fog/bog/cold, later explored the Arctic for a decade.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOOvercoming Doubt and Embracing Cringe
0:45 to 3:56
Discover the importance of handling embarrassment to pursue dreams.
“Anne was gripping the sink in her bathroom, staring into her mirror.”
The Story of Anne Daniels
3:56 to 4:49
Listen to the inspiring story of Anne Daniels' transformation into an Arctic explorer.
“I've spent the last 30 years meeting amazing people, extraordinary people.”
Swimming with Sharks: A Method for Success
4:49 to 8:52
Learn a two-part method for balancing planning and action to achieve goals.
“they became the famous person they are today.”
Doubt's Role in Our Dreams
8:52 to 9:36
Understand how to confront doubt without letting it hinder your dreams.
“Because when the meeting is over, you get your head down and you crawl.”
Transcript
Automatic transcript. May contain errors.0:00Hampus Jakobsson:I've spent the last 30 years meeting amazing people, extraordinary people. The first 10 years, I was building my two first companies, scaling them globally and finding great talent. The last 20 years, I've spent as an investor trying to find the people who build the tomorrow we want to live in. And those people, of course, they need to be extraordinary. To get anywhere interesting, you have to be able to handle cringe. Nobody likes being embarrassed. Embarrassing is the hell we're all trying to avoid, right? But if you get past that, because this is what I found, that these amazing people, is they don't spend their times ruminating and thinking.
0:42Hampus Jakobsson:They actually do. Because here's the thing. Doubt doesn't get to steal your dreams. Doubt gets an appointment with you. We are live. We are live. We are live. We are live. We are live. We are live.
1:12Hampus Jakobsson:Anne was gripping the sink in her bathroom, staring into her mirror. She was a single mother of triplets, which was the reason her husband had left her. It was also the reason that it was really hard for her to hold the job. And that was the reason why her bank account was dwindling. There was only one thing she was amassing now, and that was panic. Because the panic attacks were coming more and more often. And this morning, one of her young kids looked at her and said, Mom, you don't smile. And then it sunk in. she stared at the mirror, gripped the sink, and said to nobody, to the world, to herself, she said, you cannot go on like this, living just to keep them alive.
2:11Hampus Jakobsson:A couple of days later, she was out walking with the kids, and she passed an ad. and she looked at it and the ad said looking for women for an all-women north pole expedition she laughed out loud it was so ridiculous she'd never been on a pair of skis she didn't have a backpack she'd never spent a night in a tent so she signed up and the first test was on dartmoor in the fog, in the bog, in the cold. The first hours were gruesome. She was lost. She couldn't read a map. And that insidious mist of a fog took away the trail points right away. The other 249 women on that moor were climbers, gym instructors, athletes, professionals.
3:06Hampus Jakobsson:Some were in the back of her mind. Anne was thinking, this process is set up to weed out people like me. She was in borrowed Green Army surplus. She made that first day and the next, and she got selected to the second selection process where they were in Scotland and passed that, and then she went to the North Pole. And after that, she went on another expedition to the South Pole, And then she spent a decade as an Arctic explorer. When I interviewed Ann Daniels, I could not believe that this woman ever had been lost. She had so much power. I've spent the last 30 years meeting amazing people, extraordinary people.
4:02Hampus Jakobsson:The first 10 years, I was building my two first companies, scaling them globally and finding great talent. The last 20 years I've spent as an investor trying to find the people who build the tomorrow we want to live in. And those people, of course, they need to be extraordinary. And then what is an extraordinary person? I think we can all realize that they, of course, have amazing talent. And I think it's all proven that they have extraordinary grit. But what else do they have? And that is the thing that I've spent the last two years interviewing star chefs, celebrities, athletes, performers, CEOs, to find out who were they before they became the famous person they are today.
4:52Hampus Jakobsson:And there's one thing I found and a method. And I'm going to teach you that method today. The first thing which I'm gonna say, but it's very hard to do, but you can at least you can have heard it, is that to get anywhere interesting you have to be able to handle cringe. Nobody likes being embarrassed. Embarrassing is the hell we're all trying to avoid, right? But if you get past that, and I hope that you're brave or next week at least a little braver, then you are gonna use this method to get an interesting place. This method I call swimming with sharks. And you're going to do it with me now, at least somewhat.
5:36Hampus Jakobsson:So imagine this now. You're on a boat in a paradise place, no cyanobacteria is in the water, and you fall in. And you squint, and you see an island, and you think you probably can swim to that island because you're a great swimmer. The problem is that there are sharks in the water. And you have two ways of swimming. You can breaststroke, beautiful breaststrokes, with your head above the water, where you can think, course correct, know where you're going, plan a bit even maybe. And then you can crawl. You can crawl with so much power, but with very little direction. Okay, now comes the interactive part.
6:20Hampus Jakobsson:When you have to move your body for a second, can I get one breaststroke? It's good for your shoulders too. And then one crawl. Thank you very much. The thing is, the headache with some of you is that most of us are one of these two people. You might be an amazing planner. You love researching, thinking about what tools to use, sitting there, writing documents, pondering, maybe even worrying a bit. Recognize yourself. And some of you are action heroes. Maybe you are a person who if you could find that note with your motto, it says, ready, fire, aim. That's you. The problem is to get to that island, you have to combine them.
7:13Hampus Jakobsson:Because if you just crawl, you're gonna run out of energy and you probably will miss that island. A lot of people do. They just crawl somewhere random. And if you just breaststroke and plan and ruminate and think, as many of us do, the sharks will get us. So I'll tell you the method. And because I'm a nerd, you're going to recognize it. What you do is you use the least used app of your phone for some people and the most for others. It's the most used app for me. You're going to use your calendar. you're going to next week book a meeting with yourself and that meeting is called your breast stroke meeting you come to that meeting make it an hour at first be kind to yourself you're going to come to that meeting and during this meeting you're going to breaststroke you're going to find the island you're going to find your plan you can research tools you can read articles listen to podcasts you can do anything you want worry and ruminate but when the meeting is over you get your head down and crawl you do you do you do you go cringe you go out there on stage you publish your book you click play and when you were hit by that thought when you feel lost in the fog and you can't find the trail marks and you kind of want to ruminate a bit you just open up the next meeting with yourself that you have in two weeks which is your breaststroke meeting you open that, you just write everything in your mind to get it out of you and then you click save and close that calendar meeting and then you get your head down and you crawl and two weeks when that meeting comes up and you do the breaststrokes you open the calendar invite for yourself you come to that meeting, notifications off and you're fully focused and you read what yester you thought and you read those notes because you now have time, a whole hour, maybe two, to course correct and think.
9:14Hampus Jakobsson:Because when the meeting is over, you get your head down and you crawl. Because this is what I found, that these amazing people, is they don't spend their times ruminating and thinking, they actually do. Because here's the thing, doubt doesn't get to steal your dreams. Doubt gets an appointment with you. My book is coming out this fall. I've interviewed wonderful, amazing people, and it's going to be a great thing to have finished it, I can tell you. But I hope I gave you something of value already today. Thank you very much.
From the publisher
Hampus Jakobsson, General Partner at Pale blue dot, explains how Founders and investors can balance careful planning with decisive action when doubt takes over.
Through the true story of polar explorer Ann Daniels and his “swimming with sharks” framework, he explores:
- Why planning without action keeps you stuck
- Why speed without direction wastes energy
- How extraordinary people act before certainty arrives
Recorded at Love Tomorrow Summit, where EUVC curated the investor-focused programme.
Subscribe to EUVC for more insights.
Timestamps
- (01:00) Ann Daniels reaches a breaking point
- (02:00) An unexpected opportunity at the North Pole
- (03:00) Surviving the expedition selection process
- (04:00) What makes extraordinary people different?
- (05:00) Why you have to handle cringe
- (06:00) Breaststroke versus crawl
- (07:00) Planners, action heroes and why you need both
- (08:00) Scheduling your breaststroke meeting
- (09:00) Give doubt an appointment




