Take Control of Your Career And Create Your Own Learning Curriculum

Learning online is overwhelming. How many times have you started a class and flailed about, looking for the right next steps?

In today’s rapidly accelerating world, we’re all trying to learn as much as we can as quickly as possible. If you’re anything like me, however, this means you can quickly get overwhelmed by all the choices.

Today we get to learn from Mathias Jakobsen, Internet entrepreneur, creator of Think Clearly, and Learning Designer at Hyper Island. Mathias has also curated workshops and learning sessions for the entire team at One Month, and helped our team find our own way as we grow. He took time to share with us his thoughts on learning, online education, making your own career path, and what to do when the transition feels clunky and uncomfortable.

How to chart your own learning path — An interview with Mathias Jakobsen

Sarah: We have a lot of students who are in the middle of career transitions — they’re learning new skills so that they can either get a new job or start an entrepreneurial project on the side. What is some advice you have for students who want to learn new skills but aren’t sure how to begin, or where to start?

Mathias: Make sure to check in with your motivation.

Why do you want to learn this skill? Is it because it might make you money which might give you better life conditions? Or is it because you are truly fascinated and want to learn because you are curious? Or something else? Of course, they are not mutually exclusive, and just because you are motivated by curiosity doesn’t mean that you can’t use the skill to make more money. But I think you will always be better off if you can dare to be honest with your motivation.

I think you will always be better off if you can dare to be honest with your motivation.

If you know that your main motivation is to make more money, then you need to keep that in mind when it gets challenging. How will you deal with getting stuck when it feels like you are not making progress for hours or even days? That’s when you are most likely to give up.

Perhaps you can give yourself a set number of hours and trust that if you truly spend 100 hours trying to learn this, it doesn’t matter so much if you feel stuck for parts of it. It’s a mindset shift from certainty to probability: you will never know in advance if you will be able to learn a new skill and make money from it, but you can define clear steps and conditions that will certainly increase your probability of succeeding.

If you are truly motivated primarily by curiosity, then it will be less challenging.

But if you are not honest with yourself and tell yourself it will be easy because you are curious but actually you are motivated by something else, then when it gets difficult, you will get discouraged and give up.

It’s important to dare to dream precisely about the future you truly desire.

In my coaching work with entrepreneurs I have often helped people dream about what could be possible instead of being stuck on all the things that are currently not possible. The trick here is to be very specific and precise. For example, someone might say that they dream about more money. They also have lots of other ideas and visions, but most people I meet seem to also have this idea of “more money.”

But they have never radically considered exactly how much more money they really want, what exactly they would do with it and what that might concretely look like. Do you want $200K annual salary? Do you want a million? Why not ten million?

So I ask people to tell me how they would spend their money if they had unlimited funds. What exactly would they buy? Most people start off making variations of the same list of all the things that society teaches us that we should desire: one or more luxury homes in a various metropolises, a boat, a plane, a fancy watch or two, some cars, some people are into helicopters, all organic food from Whole Foods, a private chef and so on.

Then I ask people to be more precise and to look up the price tags on all these items so that we can figure out how much money they would actually need to get everything they can dream of. But you can’t look up the price tag of “a fancy car” so you need to decide: is it going to be an old Ferrari F40, a Mercedes AMG SLS or a Bugatti Veyron? All three?

Do the research. And where will you park them? Who will clean that beach house when you are not there? It takes time, but what happens when you keep pushing yourself to see the specific details and make all those little choices, is that suddenly the dreams begin to feel more real, and when that happens, you can begin to realize that most of these are actually not your dreams.

Imagine that life with the specific things in it that you want. Draw it. It can be very motivating.

And then you can begin peeling off the layers and uncover the things you actually want in your life. Again, with the same precision. And don’t be ashamed if you (like me) dream about a vintage Rolex GMT-master. It’s a beautiful watch. Imagine that life with the specific things in it that you want. Draw it. It can be very motivating. But you need to dare to shamelessly let your desires run wild first and go as far as you can into the wanting. See what happens.

You need to dare to shamelessly let your desires run wild first and go as far as you can into the wanting.

Why is it important to continue to re-invest in higher education as you grow older? What are the smartest leaders doing that other people aren’t doing?

Change is happening very fast today.

And the only thing that we know is that it will never again be this slow. It will only get faster. Companies have shorter life cycles. Technologies are being adopted faster. Information travels further and faster. Our skills are getting outdated all the time and need constant updating.

As I see it, learning is the only solution.

And not just this course or that course. But learning as a fundamental attitude is the only sane way to approach the future. Investing in education is just a piece of the puzzle.

What are some of the key tools and aspects of ongoing growth that you see people engaging in?

There is no tool for this. The tool of today may be outdated before I’m done with this sentence. It’s the attitude that matters.

An attitude of curiosity and openness to what’s new. You don’t need to like it or love it. But try it once or twice before making up your mind. I recently tried the new Periscope app. I thought it was stupid. But I pushed myself to try. I had so much fun. I was so surprised by how truly engaging and interesting it was. I was just walking down the street, filming, live-streaming my life and telling the camera that I was on a mission to buy ice cream for my wife. Suddenly there were people from all over the world watching, commenting, interacting and I felt like a human. I felt they cared. I truly felt that. It was incredible.

Three days later I deleted the app and I haven’t used it since. Was it a failure? Does it matter? I spent a total of about 30 minutes playing with it and now I at least have some sense of what it can do and particularly I can understand why others might love it. I explored. Get curious.

Do you see common mistakes people make when digging into self-learning and/or career transition?

People get stuck in all kinds of places. Most often people get stuck in one of these four places:

• Trying to do it alone, and thinking that they need to (and are supposed to) know in advance, rather than going into it with an explorer’s attitude and taking notes along the way as they uncover, discover and figure it out.
• Second, not taking the time to properly understand their true motivation. They set out to do something — a bit like a New Years resolution. They want to “lose weight” or “implement a new strategy” but they don’t put in the time and effort to understand why it truly personally motivates them to do this. You need to keep asking yourself “why is this important to me?” And for each answer you ask again “and why is that so important to me?” It typically takes at least seven steps, and often more. And often there are forks because there are multiple answers and each must be explored.
• Third, people fail to clearly and precisely specify the goal: how much weight to lose. What exactly they want to see as a result of the new strategy. A good guide is to ask yourself: “is the goal so clear that I could give the instructions to someone else and hire them to unambiguously judge if the goal is achieved or not?” It must be something they can actually see with their own eyes. You must be able to track your progress, even if you don’t know exactly the results you will have in advance.
• Finally, people don’t break their goals into small enough steps. They overestimate their own ability to change and they underestimate how powerful it can be to make tiny changes. If the steps are not clear enough it’s super difficult to act on it.

“Being more organized” is a great ambition to have, but what’s the step to take? Perhaps the first tiny step is to schedule just 10 minutes every week to make a list of what has been most disorganized that week. If you do that for five weeks you may not instantly become more organized but you will have better insight into what specifically is disorganized in your life.

Then the next step may be to pick one of the smallest things that kept showing up. Then, treat yourself. You are on the way to becoming a lot more organized by taking this first small and incredibly crucial step. You are shifting your perception of yourself from being disorganized to being someone who slowly but surely will become organized. And yes, this will not immediately solve your inbox and the clutter on your desk, but remember you’ve lived with the mess for years now anyway, so it can probably wait another few months.

If you could teach people three things, what would it be?

To seriously explore their own wants and desires in a precise, honest, ongoing and systematic way. Not to act on every desire, but to know what they are. And to get rid of all those that have simply been pushed onto you, as I wrote above.

I also strongly believe in taking notes and using tools that help you slow down at least temporarily. This shift in mind tempo seems to be very beneficial for seeing the longer threads that get lost in the haze of rapid (but small) changes that we see day to day.

To reflect regularly in order to integrate thinking and feeling and to discover and learn about yourself in whatever situations and experiences you go through.

To be kind to others. Both for the benefit of the other, but mainly for the benefit of oneself. Part of this is learning about yourself and what situations where you find it more difficult to be kind. Being late for a meeting and waiting on a busy subway is not a situation where I personally find it easy to be kind and let others on the train first. So I try to always be very early for things. If I haven’t eaten properly I also find it hard to be kind and sharing with others, so I try to ensure that I get proper meals. This sounds stupid when I write it, but it’s really important.

You are a learning designer with Hyper Island, a company that focuses on the development of individual and company leadership growth. Can you tell us a bit more about your work at Hyper Island and the process? What do you do, and how does it work?

Hyper Island is a creative business school, and we consult with extraordinary individuals around the world. We enable organizations and individuals to see the bigger picture, engage, and act on opportunities that arise in our digital and technological age.

My primary job is to create a learning journey for the participants, which takes them from where they are and to where they can be, using whatever resources I have available in the form of speakers, sessions, workshops and our methodology.

The first step is to know where the participants are in their lives, companies, and experiences. I often do interviews with them or others do the interviews and I read the results. For some of our open classes, there is also bit of a filter for who signs up in the first place, so it’s not completely random. However, for some of our tailored programs for companies, the interviews are absolutely crucial to understanding where they really are and what they need.

The journey has several stages and we design different experiences and elements to best suit each team. There can be a lot of variation from one workshop to another, but some of the recurring elements are:

• Build trust amongst the group. This is important for everything that comes after.
• Set a clear precedent or example of the type of participation that is expected (this is not a class where you get to lean back and just listen, you will be asked without warning to discuss a question that seemingly has no definite answer, and still come up with one clear answer in a small group, in just 120 seconds, so get used to it) This might make people uncomfortable at first. That’s part of it.
• Encourage space for self-assessment. Where am I in relation to X? Where are the others in the group?
• Gather input. This can be powerful stories, ideas, concepts.
• Lead exercises and workshops. Building on the input, pushing participants to do something with the material. Putting material into context and applying the skills they are learning enables them to take it home with them more permanently.
• Self-reflection. Participants learn “what does this mean for me?”
• Group sharing of reflections.

These are the elements of a learning journey, and within this journey, we can go through stages like “opening up and seeing the big picture” into “experimentation with a new attitude” and finally “planning, execution and implementation.”

Take us into the transformation of a participant. What are they like when they arrive, and what has changed when they leave?

People arrive with expectations.

Maybe they expect a traditional class with lectures. Others come on the recommendation of a friend, and while they have no clear understanding of what will happen, they have very high expectations because their friend told them it would be incredible.

One of the first things we ask people to do is to share something that they normally would never share with others. It catches people off guard, and with little time to prepare, most people simply go for it. They are pushed to be vulnerable in front of a whole group. I think it’s pretty intense for the participant. But it also opens up the space so much after.

Some of our speakers are really good at pushing your thinking. To let go of some of your ideas and beliefs and judgements. Or at least consider how the world would look if you saw beyond your own judgement. That others might see it differently.

By the end of the first day most people express that they feel that their head is spinning. People report not being able to fall asleep.

The morning of the second day it’s time for quiet reflection and introspection. I love this part of the journey. We ask people to write down their answers to a set of questions that gently guide people into their memory, then into their emotions, then into critical thinking and eventually to consider larger implications of their new insights. It all happens individually, in silence at first.

Because most people don’t take the time (or have the time) to sit quietly and reflect, it can be super powerful.

It’s legitimate because the facilitator asked you to do it, and everyone else is doing it. I personally hate when some senior executive feels that he is so important that he must check his e-mail during those minutes. It’s like pissing on everyone else.

The second day of the journey is very creative and the experience for most people is that they suddenly tap into creative resources they never knew they had. It’s hugely empowering. The climax is typically at the end of day two.

On the last day it’s time to gather the new learnings and come back down to earth. To devise concrete action plans for putting the new stuff into practice. To solidify the learnings into an understanding or a framework that they can take with them.

When they leave they are less afraid.

They often say this out loud, but even if they don’t I can feel it. That’s probably one of the main reasons why I work here. It’s so hard to think clearly when there is fear. We help people leave lighter, less afraid.

As a school, you do this predominantly through face-to-face interactions. Tell us more about why in-person interaction is such an important tool.

Most people have really bad habits when they are in front of a laptop. The rapid Cmd-tab multi tasking shortcut is so hardwired into my brain that if an app or site is remotely unresponsive I will instinctively jump to another app or site while I wait.

Even if I have nothing to do there I just do it because it feels like I’m wasting time waiting for something else. This might be rational from a certain efficiency perspective. Back in the day when downloading a large PDF might have taken 50 minutes, I’m probably better off writing a few e-mails rather than waiting for the file to download while staring at the progress indicator.

But today the lag might be half a second before I switch. All it does is make me feel scattered and it’s simply a bad habit that I haven’t managed to change. I think we all have such habits, which most of the time are not that big a deal, especially if we are doing lots of little admin-style tasks, responding to tweets and other things that require no more than 3 second bursts of concentration. But for learning we often need more focus. Especially if we are trying to learn something that is not easy.

Face-to-face is by no means a silver bullet for this. Many learnings environments are so dull and boring and disengaging that you are probably better off just randomly surfing interesting Wikipedia articles on your phone than paying attention to the lecture or training that is being presented. We have all been there. It sucks.

You can make both online and offline teaching boring as hell.

However, let’s consider a session that is highly engaging but with content that is also difficult, challenging and hard to comprehend. For this I think that face-to-face sessions with a group, the way we do it at Hyper Island and many other places, can significantly help people stay focused and engaged because there is interaction and because it’s very easy to see that nobody else is “checking out” with their phones so it creates a social pressure to not do so.

The room creates a certain force of attention which both fuels the presenter with energy but also makes it less demanding for the participants to hold the attention because it’s already flowing in the room.

The other thing that can be much more effective in person-to-person, is building trust, which can be crucial if you want to have an engaged and engaging conversation or discussion in a learning environment. Trust can of course also be created online, but in my opinion it just takes a lot more time and effort. Probably because we have less non-verbal communication (body language, scents, touch etc.).

One of our challenges at One Month is in building this type of community online: in your perspective, what are the pros and cons of online education? When does each thrive?

I obviously love doing live, in-person learning experiences, but I am also realizing that it has so many limitations. It really doesn’t scale well: if you add more than 30 people in the same room you begin to lose the interactive experience, and it becomes like a conference instead.

It’s also geographically limited to people who are in close proximity to each other, or who are willing to travel. For brief learning sprints of 2–3 days this is not an issue, but if you want to really go deep in something it’s usually better to come together as a group on a weekly basis and then do individual exploration in between.

At Hyper Island we don’t believe that online education can replace some of the personal and organizational transformation work we do through our courses, but we do believe that integrating the online and offline can be tremendous. By using both, you can create a blended experience where some of the early trust building work happens in person and most of the deep dive and implementation happens virtually.

This allows us create much more valuable learning experiences. We are curiously exploring and experimenting in this space. We definitely haven’t solved it yet, but the opportunities are so massive and the fact that it has transformative potential on a truly global scale makes me really excited.

When does online learning excel? What is special about being online and connected in a way that we can’t do in person?

What online can do much better is to make the learning path individual. Each person can move in their own tempo and it can even be non-linear. One might choose a different order of learning.

What online can do much better is to make the learning path individual.

You can also do a lot of things that are not synchronised. This allows people to learn together from completely different locations and time zones.

I think online learning can excel when:

• It’s social — an actual group of people who are learning together and who are committed to getting to know each other just like you would naturally do offline. This means taking the extra time to build trust. To small talk. To talk about the stuff we care about personally outside of the stuff we are learning. Who we are as people. What we dream about. I think it’s best when it’s a pretty small group. Even if the small group is also part of a huge group, I think a sub group of 5–10 people is ideal online. Everyone takes the time to have 1:1 conversations. Using something like the NYTimes 36 questions to fall in love, could be a simple 30 minutes activity that everyone does with each other (that’s two full hours for each person in a group of five)
• What is to be learned is already well documented on the Internet at large (most stuff is today)
• The teacher’s main job is to give the group the questions and directions for exploration.
• Assignments that the group must solve together or maybe in pairs and which has some form of creative output. The teacher knows that it can be solved. The teacher has defined a reasonable format and time frame for the task. And the teacher is available for support if anyone gets really stuck.
• The groups present their findings to each other.
• The teacher also designs the experience so that there is a reasonable progression and adjusts based on the feedback of how well the groups solve the challenges. So the initial exercises are simpler and require few steps but they build up resources, knowledge and confidence which can be incorporated in later and more complex challenges.

You also write a newsletter, Think Clearly, based on your years of work with entrepreneurs and business leaders. What is the process you use when working with entrepreneurs? How do you help them clarify the noise and focus on what’s important?

I listen and ask questions.

More concretely, I have also used certain spaces and places that are not so ordinary, in order to help people get out of their normal habits.

A busy coffee shop can be fine for some meetings and for long time clients where we have built our habits and ways for working, we can do the conversation in the most distracting place and still be 100% focused.

But when you are first starting out, a quiet and slightly strange place can simply be more effective. I have used the lobby in the TriBeCa Grand Hotel for years. They serve great coffee, the staff is super friendly, and it’s quiet with high ceilings and skylights, yet, dark and intimate. It’s perfect.

You recently had a brand-new baby. How has she helped you reconsider the world? What do you see about the world through your children’s eyes?

The three things I want to teach everyone (above) are probably what I will teach my kids.

I think being a father is amazing for me. I feel so grounded in that experience and in having a family where there is so much love flowing around. My wife is incredible.

No matter how many miles I fly away to the other side of the planet to run some workshop, I feel grounded in them and I am happy that I both get to go away and then to come back home.

I learned that it’s very important for me to be doing work that I truly care about. Because then I take the energy I get from home and invest in my work, and I get a different kind of energy from doing the work which I can then bring home.

I also realize that while I have very reasonable hours at Hyper Island (I work pretty much exactly 40 hours per week), I still don’t see my kids that much. I see Noah for an hour in the morning and an hour in the evening and then on the weekend. But I know that when we are together, I’m a dad that brings home energy from doing something that matters to me. I work because it matters. It also pays for our rent, but I honestly feel that’s an added bonus. If I were independently wealthy I would still go out and do work that I care about because I want my kids to see that.

We’ve talked before about the magic in the mundane — how the smallest of things can make the biggest difference in life changes. What mundane things are magical in your own life? Can you give a few examples?

Magic: baking bread. Mixing flour and water and salt and making delicious food. Baked loaf 326 yesterday.

Changing a diaper can be such a rewarding experience. When I pay attention it has a lovely mix of intimacy but also efficient choreography of moves and swipes which can truly be mastered as an art form.

Sometimes just seeing the lit up NYC skyline from the packed subway car passing over the Williamsburg bridge after a long day.

What’s the biggest lesson you’ve learned this year, personally?

That my kryptonite is that I want to be liked by others.

I realized this a few weeks ago and it is so hugely liberating to know that this is the case. I think it is quite common actually, but I never knew for myself, and it limited my scope of action. From now on I may still limit my scope of action, because I still want to be liked.

But now I know it and it is my choice, and I know I can also choose a different action outside of that scope if I am just willing to risk not being liked. I tried it recently and it was hugely empowering even though it was such a tiny thing.