Life Design

How to fail at everything and still succeed

Life has been taken over by preparations for our move to Philly. This has taken the form of trying to get together (safely) with friends before we leave, preparation for school, and packing. Lots and lots of packing.

It also has been a time of introspection. There’s a lot I don’t know about how my life is going to change in the next month, but one of the things I am fairly confident of is that I am about to be inundated with tantalizing opportunities to invest my time and efforts. As such, I have been thinking about what I want to make sure I focus on and prioritize once school starts.

As sometimes happens to me, this short-term question exploded into a long-term one. Not just where do I want to prioritize my time over the next 2 years, but what do I want to prioritize over the rest of my life? (This thinking lines up well with some of the thoughts I have been having on the Power of Identity.)

As I pondered this, the question struck me “What are the handful of things I could succeed at that would allow me to fail at everything else and still win?”

Put another way, how could I fail at everything else and still succeed?

I have spent the last couple of days thinking about this question and here are the endeavors I came up with.

A quick note before digging in. At times, this may wander near dangerously “preachy” sounding territory. At others, this may sound like banal self-help platitudes. Trust that the below is an earnest attempt at outlining what I believe to be answers to important questions. They are likely not the only answers and yours may differ compared to mine. I do not have this stuff all figured out. I am 26. I am happy with where I am at on some of these pursuits (I think I knocked #2 below absolutely out of the park), but others are still very much a work in progress. Remember this exercise started with thinking about where I wanted to prioritize my time. Hopefully, these rules can be a guidepost for you and me both.

Without further ado, the 5 things you can do to succeed, even if you fail at everything else:

Live Within Your Means

This is perhaps the phrase that has been hammered into my skull more completely than any other. It was a frequent favorite of my parents growing up and they still refer to it regularly. The idea here is to give yourself breathing room. Life happens. It takes all sorts of twists and turns. Your resiliency to low points could very well have just as much to do with your ability to follow this rule as any sort of personal amount of grit or drive. Living within your means is both downside protection and upside optimization. On the downside, it gives your breathing room and the ability to handle nasty surprises. On the upside, it gives you the flexibility to be able to take advantage of serendipity when it knocks on your door. I am a big believer in the idea that everyone gets lucky breaks in their life, but very few take advantage of them. Living within your means allows you to do just that.

Now I am not advocating a lifestyle of a modern hermit. You can definitely take this one too far and budget yourself into a pulp. Instead, think about what you care about and allocate money there. I am not a big car guy and likely never will be. But I love to travel and that’s something I would definitely like to do more of in the future. I care more about location in an apartment/house than appliances or square feet. You gotta decide for yourself what is or is not important. There are a million best practices for living within your means. Caitlyn and I use a tool called YNAB that really helps us keep on track with our budget through monthly check-ins.

By far the biggest thing you can do to live within your means is to select a home or apartment that is within your budget. The general recommendation is to spend about 30% of your gross monthly income on rent. I’ve always tried to get that number closer to 20% (not always succeeding). For most people, their rent/mortgage will be their biggest single monthly outlay and as such the easiest one to suddenly become an undue burden.

The last really important thing that living within your means can do is to help you safeguard your ethical well-being. Sound a little melodramatic? I don’t think it is. Otherwise good people do bad things when they find themselves backed into a corner. Giving yourself extra financial flexibility helps to minimize the chances of you ever compromising yourself because you feel like you have to. You always want to have “screw you” money. Enough money that you can tell your boss to take a hike if they ever pressure you into doing something unethical. You can question whether stealing an apple to feed your family is moral, but by far the better solution is to make the choices that mean that question is never necessary in the first place.

Marry Your Best Friend

Ever heard the phrase “you are the sum of the 5 people you spend the most time with”? Well, whoever you chose to spend your life with will have more of an impact on who you are than the other 4 combined. The world is very skilled at making us believe every choice we make is the most important choice in the world. I’d argue that the only one that really rises to that incredibly high bar is who you choose to marry. This choice is the one with more leverage than any other. Choose correctly and you have a very high likelihood of life working out. Choose incorrectly and it will likely have unpleasant and longlasting ramifications. Now I can’t tell you what makes a healthy and happy couple. That is probably different for everyone.

But if I had to give one piece of advice it would be to marry your best friend. If you get this one thing right, everything else seems to kinda take care of itself. I’ve been married for 2 years, 9 months, and 5 days. I am not the world’s foremost expert on the subject of marriage. But I may be the world’s biggest advocate.

The past 2 years, 9 months, and 5 days have been the best of my life. There is nothing quite like having someone who you can trust so utterly and completely. Who has your back against the rest of the world. Who you don’t agree with on everything, but you agree with on the big things. Someone you can more easily picture growing old with than looking good on your honeymoon with. Someone who fills your life, not with happiness, but joy.

I got married young, but that doesn’t mean that it is for everyone. If it is for you, great! It definitely was for me and it has been awesome. If it isn’t, that is totally fine too. Just don’t fall into the trap of being afraid of commitment. I worry that my generation is more interested in freedom than it is in meaning. In my experience, meaning more often comes from responsibility than freedom. I worry that people chase freedom expecting that if they finally found it, their life’s meaning would somehow magically appear. You are much more likely to find that meaning once you commit yourself to something. Or someone.

Freedom < meaning. And meaning comes from responsibility. And boy is marriage one of the quickest ways to increase the amount of responsibility in your life. It isn’t always easy, but with the right partner on your team, it is worth it. It takes a lot of work, a lot of faith, and a lot of grace. But believe that a life shared is a life made whole.

Take Care Of Your Health

In every sense of the word. Physical, mental, spiritual, emotional. Your health is another great leverage function. If you are in bad health in any of the four aforementioned ways it will lead to negative impacts on your life. Maybe not today and maybe not tomorrow, but health is one of those things that has a nasty habit of eventually catching up to you (and often at the most inopportune times). This has been an increased area of focus for me recently. I’ve realized that my health is not just about me. It is about being at my best personally and professionally. It is about making sure that I will be there for my family. It is about having the energy to be present and engaged with my wife after work. And it is about reaching the potential I know that I have.

A few quick rules I have found effective.

Exercise regularly. Spend time outside. Eat everything in moderation except fruits and vegetables. Eat as much of that as you want. Avoid falling into the trap of thinking that every meal is a “special occasion” (I am a certified black belt in the mental karate necessary to talk myself into thinking that lunch on a random Tuesday is a culminating reward of my entire life’s work). When you are “on”, be “on” and when you are “off” be “off”. Spend >0 minutes every day investing in your spiritual wellbeing through prayer, reading your holy words, or meditation. Focus on the things you have control over and don’t stress out about the things you don’t. If you are unhappy about something, do something about it. Appreciate the good things you have in life and focus on acknowledging all that you are grateful for. Make sure you have one thing you are looking forward to every single day, no matter how big or how small.

Do Something Meaningful

It seems like you fall into one of two camps. Either the “Follow your passion” camp who believes that you are entitled to make a living doing whatever you enjoy most. Or the “work is work” camp that thinks if work was supposed to be rainbows and butterflies they would call it rainbows and butterflies. I’d like to offer an alternative narrative.

Do something meaningful.

This is different than following your passion. Doing something meaningful isn’t always fun. Often it isn’t. But I believe that is what makes it worthwhile. It is about doing something greater than yourself. Doing something that moves the world towards a higher state of being. Doing something that pushes back the darkness to expand the light. I believe that at our core, meaning is something that every single one of us yearns for. For an acknowledgment of how we fit into the world and that our existence matters. What you do can be an avenue to that, but only if it is something that is meaningful.

I believe the key to this is finding something where the process is its own reward. If you find something that you find meaningful, irrespective of any outcome like money or fame, you are probably on the right track.

In the words of the Knights Radiant, “Journey before destination.”

Avoid Blowing Up

Ok, so this one is a bit cheating. This isn’t something you actively do so much as it is an active practice of avoiding certain things. You avoid “blowing up” by avoiding doing things that could cause you financial, emotional, or physical ruin. Life is uncertain and disaster can strike at any time, but there are definitely activities that increase disaster’s chance of knocking on our doorstep.

An important aspect of this is maintaining proper perspective. A naturally long-lived life gives you plenty of opportunities to change and succeed. If you wanted to you could have multiple successful careers. Take the tract of optimizing for the long-term over the short. Avoid doing things that have a chance, even a tiny one, of absolute catastrophe. If 2020 has taught us anything it is that black swan events happen. Based on the regularity with which airlines get bailed out, it seems like they happen every decade or so in the financial markets.

To a certain degree, this advice is impossible to really follow since an aspect of almost every blow up is chance. But you can engage in activities that decrease those chances and avoid activities that increase them. Avoid metaphorical bungee jumps. Just doesn’t seem worth it for the risks. But then again I am not great with heights so maybe that is just my genetic makeup talking.

abergseyeview erik berg 5 rules for success

Alright. That’s what I got. These 5 rules are the strategies I believe will make me successful in life. I don’t think any of them are a secret, but as with most wisdom, the doing is harder than the hearing.

What have been the rules you’ve followed for success in life?

What are the things that you have done that allow you to fail at everything in life and still succeed?

Until next week.


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Pink Dragons, Serendipity Vehicles, and Mentos

Serendipity Startups Tech Venture Capital

When I was a kid one of my all time favorite things to do on friday nights was to have a movie night (who am I kidding, that is still one of my favorite things to do). My mom and I would go to Blockbuster to pick out a movie or two and then we would skip next store to Papa Murphy’s to pick up some pizza (I will contend till my dying breath Papa Murphy’s is by far the most underrated pizza on the planet. So good). One of the movies I distinctly remember watching during multiple movie nights was Serendipity The Pink Dragon. Serendipity was a pink sea dragon who lived on a magical island with all of her friends learning life lessons about friendship. I have no idea why we ever picked this particular movie out, but I do remember watching it more than once (to this day, my go to nickname for a Lapras in any Pokemon game is Serendipity).

I was reminded of Serendipity the pink dragon while listening to this interview from Sara Dietschy with Nik Sharma and David Perell. This episode is definitely worth listening to. They cover a lot of ground from influencer marketing to direct-to-consumer brands to their own stories and how they got where they are today. As part of this last part, they spoke about the role that serendipity had in each of their lives. They drew a line in the sand between serendipity and luck. Luck is something good that just happens to you. Serendipity is something good that happens to you because your hard work and patience put you in a position where it could happen to you. I love this distinction.

If you talk to anyone with a modicum of success in life, the vast majority can point to a handful of “lucky” events where they caught a break or were given a chance to take on a project they were woefully underqualified for. Rare, however, is the successful person who had this happen to them while watching Netflix and eating cheetos on a Thursday afternoon.

Luck is a factor in everyone’s story. What differs is how prepared people are to take advantage of the situation when the dice start rolling their way.

That is where Serendipity Vehicles come in.

Serendipity Vehicles are a concept coined by David Perell in this post. He talks about purposefully building structures that increase the likelihood of both serendipitous things happening to you as well as increasing the chances that you are able to take advantage of them when they occur. Serendipity vehicles can range from simple structures like attending a dinner party to more much more complex things like writing books.

This blog is one of my serendipity vehicles. Twitter is another. Both require relatively minimal, but consistent, effort to maintain. Both have lead to significant outsized opportunities far and above what I would’ve ever expected.

Now all of this talk of lifestyle design may sound complicated, but I think the most important thing is simply the way you approach it. I think the best way to think about designing your serendipity vehicles is to make yourself into a Mentos. Mentos are a type of spherical candy that are sold all across the world. To be perfectly honest, I think they are pretty average. What is not average are the explosive effects they have when combined with any sort of carbonated beverage (but especially Diet Coke). There is a whole lot of science behind why this happens, but the short of it is that even though Mentos looks like smooth spheres, on a microscopic level their surfaces are very rough. This increased surface area acts environments where bubbles can form, launching soda up into the air. The key is the surface area.

You can make your life resemble Mentos by increasing your surface area so you have a lot of different places where serendipity bubbles can form.

Say yes to thing even if they are outside your comfort zone.

Cultivate curiosity in a broad range of subjects and areas.

Go out of your way to go to new places and meet new people.

Jump at opportunities even if the timing is not always ideal.

Create excuses to talk with interesting people.

Provide value to people instead of just asks.

At the end of the day, your goal should be to have as many areas in your life where serendipity can form as possible The challenge is to recognize serendipity and then make sure you are able to take advantage of it.

This advice is equally true for both individuals and startups.

Well designed startups are a lot like giant serendipity vehicles. A lot of work goes into designing them so that they are in a position to shoot for the stars as soon as a serendipitous customer connection or technological development breaks their way. As a founder you need to balance the need to stay focused on what you are building with providing yourself as much surface area as possible in order to take advantage of connections with investors, talent, customers, etc.

I can’t tell you what the right balance for that is. You will need to figure that out for yourself. But I can tell you what the wrong balances are. There are two.

1) Ignoring any thought of the outside world to focus solely on your business.

2) Ignoring your business to focus solely on hoping something happens in the outside world.

Everything in between is fair game.

No matter where you land on the spectrum between focusing your time and energy on building your business and increasing your surface area to optimize for serendipity, there is one lever that you can pull to maximize your chances for success.

Burning responsibly.

Responsibly managing your burn rate as a startup is one of the most important things you do as a founder. Burn too fast and you won’t get enough at bats to have something serendipitous happen for your business, no matter how much you optimize for it.

As an individual and as a business, design your life so that you can take advantage of serendipity when it comes knocking at your door.

That is how you and your company achieve success.