1. Autonomy

Pro: you’re the boss and decide what to do.

Con: you HAVE to always decide what to do. There will be a huge array of options at any given moment, and you’ll never know for sure which to work on. You can seek advice, but ultimately YOU are the one who must decide.

2. Lifestyle

Pro: since you’re the boss, you’ll have flexibility in your hours.

Cons: you’ll inevitably be working a lot of hours. It takes a lot of work to succeed as an entrepreneur. Since there is never an end to how much work can be done, you may have trouble “turning off” at the end of the day or on the weekend.

3. Resilience

Pro: it’s an incredible way to train resilience, persistence, and problem-solving skills.

Con: the world will punch you in the face between 5 and 100 times, and if you ever give up, you lose. This is stressful, and most humans would give up after 5 or 10 face punches.

4. Expected Value

Pro: if you’re well suited to it and work on a good idea, the expected (mean) value in terms of potential impact and monetary reward can be REALLY high. Some companies have truly altered the course of history. And obviously, many of the wealthiest people are entrepreneurs.

Con: the probability of failure is high, and luck is a significant factor. And unless you have substantial savings, you’ll likely be living frugally at first.

5. Learning

Pro: you will learn a tremendous amount. Even if the startup doesn’t work out, this valuable experience will apply to MANY other things. I don’t know of another way to learn so many things so quickly. One of the most important categories of things you’ll learn is “how to get difficult shit done in the real world while charting a path yourself for how to make it happen.”

Con: you will inevitably make many mistakes (ouch), and you have to face up to them (double ouch) in order to learn fast enough. It forces you to acknowledge and improve (or develop workarounds for) your weaknesses. It’s also important to note that if you are really not suited for entrepreneurship, or you just get unlucky right away, you might not learn that much. The great learning from entrepreneurship certainly doesn’t require success, but if you fail too immediately or don’t get anywhere close to success, it will be much less of a learning experience.

6. Meaning

Pro: you can choose to work on an idea that is DEEPLY meaningful to you. Most jobs don’t provide this level of meaning.

Con: if you fail, you will have invested a lot of time in (and then failed at) something deeply meaningful to you.

7. Respect

Pro: many people have a lot of respect for entrepreneurs, and it’s considered cool in plenty of circles.

Con: this respect increasingly kicks in as success increases, and before that, some people won’t even respect it as a career choice. If you fail, that will still garner respect from some people, but most people probably won’t give you much respect for having tried and failed.

8. Relationships

Pro: you will likely meet lots of interesting people and build meaningful relationships with your team members.

Cons: you may have to deal with difficult personalities or navigate complex human dynamics when it comes to employees, investors, customers, and/or co-founders.

9. Responsibility

Pro: it teaches you a deep form of responsibility, which strengthens your character.

Con: you are ultimately, at the end of the day, responsible for everything. You’re the captain, the last line of defense, and the goalie. When someone else at your company screws up, and it ends up having a bad effect on the business, as unfair as it may seem, it’s actually your fault. You hired them, or didn’t put safety measures in place, or didn’t spot the problem early enough, or didn’t give them the training they needed, etc. The captain is responsible for the fate of the ship and every crew member on it.

10. Adaptability

Pro: it hones your creativity and adaptability, can really build self-confidence, and can help you develop a sense of how much you’re capable of (probably more than you think!) as you figure out solutions for complex challenges, develop new ideas, and map out how to make them a reality. It pushes your boundaries in new ways and makes you grow.

Con: it can stretch your creativity and adaptability to the limit. Plans, essential as they are to make, rarely survive their collision with reality. It sometimes pushes your boundaries more than you would like and can place you into situations that you find terrifying (e.g., a high-stakes negotiation to save your company when it is on the brink of failure, or a major technical failure that leaves hundreds of customers furious at you, etc.).

So, why NOT be an entrepreneur? Because it’s a high-risk, chaotic, stressful, responsibility-filled, boundary-pushing, challenging life. And it’s hard work. Not everyone is suited to this path, and it’s irresponsible to pretend that everyone is.

BUT, if you’re well suited for it, it can be one of the most deeply meaningful, high-value, high-impact lives to lead. You’ll meet lots of people, build resilience and adaptability, push your skills to new heights, and learn a STAGGERING amount. For some people, it is absolutely their best life path.

If you think that entrepreneurship may be the right path for you, and you haven’t yet picked what idea to work on, you may be interested in learning more about our work at Spark Wave. We’re a startup studio (venture builder), and we recruit people who are interested in becoming CEOs for our mission-driven software products (no technical background or prior startup experience is required). We aim to reduce some of the worst negatives of entrepreneurship while building products that we believe could add a lot of value to the world. Our goal is to help make a better world through software and entrepreneurship. You can learn more and get in touch with us at: https://www.sparkwave.tech

This piece was first written on September 3, 2020, and first appeared on this site on July 29, 2022.

I think one of the big choices to be made in life (once basic needs are well met) is whether to try to optimize more for a life of stability or for a life of acceleration. There is a tension between these two types of lives because they imply making different decisions in many realms.

From what I can tell, the significant majority of people on this planet (even among those who have their basic needs already well met) seek a life that is more one of stability than one of acceleration. And I think that, to many, stability epitomizes most elements of what it means to live “the good life”: forge friendships you can keep for decades, find work you can be a master of, meet a life partner with compatible goals and values, buy a house you will live in indefinitely, spend your free time doing the hobbies you love most, etc.

Yet, in some social circles I encounter in New York and San Francisco, the presumption seems to be that acceleration is the obviously superior goal.

So which do you seek more: stability or acceleration?

Optimizing for stability may involve things like…

(1) hobbies: figuring out what you enjoy doing most and doing those things whenever you have time,

(2) friendship: figuring out who you like being around and turning that group into your permanent circle that you spend almost all your social time with,

(3) work: getting skilled at some type of work that provides the lifestyle you want and doing that thing you’ve mastered day after day,

(4) risk: avoiding substantial risks, even if they have high expected value, or avoiding situations that seem very difficult or that provoke anxiety,

(5) romance: finding a reliable partner who shares most of your values and long term goals,

(6) beliefs: being skeptical of bizarre or wacky ideas, especially if they contradict your deeply held beliefs or challenge what has worked well for you,

(7) location: finding the place you want to be and putting down permanent roots,

(8) behavior: developing habits that work well for you and making them permanent,

(9) self-improvement: working on the behaviors or traits you have that increase instability in your life, for instance, those that cause conflict with people you care about or that make you unhappy in your current situation,

(10) mindset: treating your values as relatively static (i.e., you value what you value), your talent level as relatively fixed (i.e., fixed rather than growth mindset), mistakes as something you should seek to minimize, your optimization procedure as seeking something “good” rather than spending more time attempting to find “the best” (i.e., “satisficing” instead of maximizing), “exploitation” (as opposed to exploration – “exploitation” in this context doesn’t refer to exploiting people but refers to going with the best things you’ve found so far), and

A focus on stability may also be associated with: conservativeness (“if we’ve always done it this way and it’s worked for us, why change things?”), older age (“I’ve already explored enough”), and coming from a region/upbringing with economic or structural instability (e.g., “I want the stability I never had”).

On the other hand, optimizing for acceleration may involve things like…

(1) hobbies: regularly trying new activities, including ones that you don’t predict you’ll enjoy much, or doing hobbies that cause perpetual learning,

(2) friendship: regularly making new friends and interacting with people that are different from the ones you already know,

(3) work: switching jobs or pushing to get promoted whenever your work feels too routine or easy, or when it feels like you’re not pushed right to the edge of your ability,

(4) risk: periodically taking significant risks when you think the expected value is high, or throwing yourself into situations that are very difficult or anxiety-provoking when you believe they will make you better in the long-run,

(5) romance: finding a partner that challenges you to become a better version of yourself, or to do things outside of your comfort zone, or that you can learn a lot from,

(6) beliefs: taking bizarre or wacky-seeming ideas seriously before deciding whether to reject them (at least, when they come from sources you have respect for), even when they challenge your basic premises or lifestyle,

(7) location: exploring many different places to live (e.g., countries or regions) and environments to live in (e.g., alone/with groups, around different subcultures),

(8) behavior: regularly discarding old routines and trying on new ones to see if they have benefits, or resisting making routines at all,

(9) self-improvement: pushing yourself to always learn new things and to work on the behaviors or mental habits you have that may be limiting your potential, and

(10) mindset: thinking of your values as continually evolving, believing you can improve yourself in nearly any capacity if you work hard enough (i.e., growth mindset), treating mistakes are an opportunity to learn and as a positive sign that you are trying things that are sufficiently hard, and believing you should strive to do the very best you can and to be the very best you can be.

A focus on acceleration may also be associated with: liberalness (“we should be open to and learn from the ideas and practices of those who are very different from us”), younger age (“I want to explore all that’s out there”), and coming from a region/upbringing of abundance (e.g., “I want something even better than what I had”).

Note that acceleration is not necessarily exponential. In many cases, especially when trying to accelerate an area that you’ve already spent a lot of time working on, improvements will be slow and linear (whereas acceleration may be rapid in areas where you’ve done relatively little optimization before).

Some life choices cause an interesting mix of focus on stability and acceleration. For instance, having children is, I think, very much an action that drives acceleration: it annihilates routines, carries significant risk, speeds up maturity, and challenges you to be a better, more selfless person. On the other hand, once you have a child, there is pressure to seek stability for the sake of that child. So perhaps it is a choice that produces a focus on acceleration in the short term but on stability in the long term.

Of course, you can seek stability in some areas (e.g., romance) while seeking acceleration in others (e.g., work), but I think as a simple, compressed model, it can be useful at times to view stability and acceleration as existing along a continuum.

Some people seek neither stability nor acceleration, but I don’t think it is terribly common to seek neither of these for a large proportion of life. Counterexamples, though, would include hedonists focussed on maximizing their pleasure and a subset of people with long-term severe depression who have stopped actively seeking any improvements to their life (perhaps due to “learned helplessness”).

The idea of stability vs. acceleration is related to (and includes in it) the idea of an “exploration vs. exploitation” tradeoff (discussed in the machine learning literature, and more recently, in a self-improvement context). However, I intend this concept to be much more general, as it also encompasses ideas like risk aversion, openness to ideas that challenge your lifestyle, and how you choose to direct your self-improvement efforts.

I don’t think that either stability or acceleration is “better” than the other. Where you should ideally fall on the spectrum right now depends heavily on what you value, as well as your life circumstances and opportunities. You may choose to emphasize stability at one point in your life and acceleration during another, or you may be caught right in the middle, trying to strike a balance between the two (even as they tend to be in tension against each other).

• The new thing seems likely to be beneficial or enjoyable OR is different enough from things you’ve done in the past that you don’t think you can accurately predict how you’ll react to it

• Trying the new thing doesn’t require a substantial investment of time or resources AND is extremely unlikely to cause you long term or significant amounts of harm (or cause other people harm at all)

Personally, I almost always accept the chance to try new things when they meet these criteria. There obviously isn’t much point in pushing yourself to do new things that you don’t consider valuable (e.g., punching yourself in the head), unless of course, your model for what is valuable for you is not very accurate (e.g., maybe you think there would be no value in doing an improv class, but actually it would teach you useful skills and help you overcome fears).

The benefits of trying new things:

• Sometimes you’ll discover new things you really like, which you can then choose to do many times in your life (e.g., by trying mixed martial arts I learned that I really like it, and it became a hobby as well as a method of staying fit)
• Building a more accurate model of yourself, which you can use to predict your responses to other things in the future (e.g., by going to a tea tasting, I discovered a lot about my tea preferences, including the fact that I typically prefer mid-priced teas over both expensive and cheap teas)
• Gaining a better understanding of what the thing is and why others might enjoy it (even if you don’t end up liking it yourself), hence deepening your ability to relate to others (e.g., spending a day going bird watching, which is definitely never going to turn into a hobby, but which gave me a greater understanding of people who take joy in cataloging activities and of the richness in those sorts of activities)
• Deepening your knowledge of how things work or of the variety that exists in the world (e.g., taking a tour of a traditional home in Bali taught me about some interesting differences in living arrangements and burial practices across cultures that I hadn’t previously known about)
• If the thing makes you irrationally afraid, challenging that fear and teaching yourself to push through (unfounded) fear more generally. There often is value in challenging yourself to do things you are afraid of that you know are not actually dangerous because, in addition to the benefits of the new thing itself, it helps ensure that you don’t let fear prevent you from getting the most out of life (e.g., taking opportunities to speak in front of a group when I had very little time for preparation and knew I would have to do substantial portions off the cuff)
• Causing a positive change in yourself (e.g., trying meditation made me more aware of the way in which my mind is not usually fully focused on just one thing and what an alternative might look like)
• Potentially deepening relationships with others, either by doing the new thing with people you already know (creating a memorable shared experience) or meeting people during the new activity

Possible drawbacks of trying new things are:

• They take time, and sometimes other resources like money as well.
• They are sometimes unpleasant while you are doing them (though this is mitigated when they are the sort of thing you can stop in the middle if you want)
• They can (in rare cases) be traumatic or cause long term harm.

Overall, I suggest using the rule of thumb: “if it is new to me, relatively easy to try, and not likely to be harmful but may yield benefits, I should try it.” I think that following that heuristic will usually leave your life richer, more enjoyable, and more full of growth than the alternative.

You can, of course, proactively seek out new experiences, rather than waiting around for opportunities to arise (e.g., committing 2% of your free time to new things).

Here are some activities you could consider trying, if new to you:

Experiential

• spending a day listening to many different types of music that you wouldn’t normally listen to
• asking your friends for their favorite movies and then watching the ones that you wouldn’t normally choose to watch
• beginning a daily practice of writing in a journal
• miracle berries
• eye gazing
• going to Burning Man
• traveling alone in a foreign city
• going a week or longer without electronic devices
• going blindfolded for a day while still trying to do your daily activities at home
• wearing earplugs for a day while still trying to do your daily activities at home
• fostering a pet
• trying a totally new diet (e.g., going vegan for a week)
• jotting down your dreams each day when you wake
• making a list of 3 things you’re grateful for every night before bed
• making a list of 3 things that went well today and what caused each to go well each night before bed
• thinking of one thing you’re excited about each morning as soon as you wake up
• going to a therapist
• fantasizing about something you’d never normally fantasize about or trying to come up with a new fantasy that you find highly appealing
• volunteering for a day to work with people in need
• having a week where you spend at most only a tiny (fixed in advance) amount of money each day
• trying a new cuisine
• cutting out caffeine for two weeks
• cutting out all unhealthy foods for two weeks (by whatever your metric for “unhealthy” is)
• not watching any TV for two weeks
• exercising every day for two weeks
• spending a whole day trying to be as aware as you can of each of the thoughts you have
• spending a whole day trying to be fully optimistic about everything that happens
• spending a day where you only allow yourself to do fun things
• cuddling non-sexually with a consenting close friend
• buying a few healthy snacks that you’d not normally try and see if you like any of them
• observe carefully in a mirror how exactly your face changes when you make expressions of fear, anger, surprise, happiness, sadness, and contempt
• walking a route home that you have never taken
• consciously designing an adventure for yourself and some friends and then going on it together
• imagine a future life for yourself that you’ve never seriously considered
• house sitting for a month in a place you’d never considered living permanently
• running or sprinting a few times per week
• going to a convention or conference about something you really like
• spending two full days without communicating with another human being

Skills

• toastmasters (for public speaking practice)
• tying martial arts
• meditating daily for a month
• massage lessons or practice
• cooking class
• improvisation class or acting
• creating art of a form you wouldn’t normally attempt
• giving a lecture on a topic that interests you
• trying a team sport you’ve never played
• try high-intensity interval training daily for a week
• trying a form of exercise you’d never done before
• language classes (e.g., sign language)
• circus arts
• explore a nearby neighborhood that you’ve never explored
• go to a familiar neighborhood and try to notice ten things you’ve never noticed before

Social

• organizing a retreat for your close friends
• throwing a themed party or social experiment of your own invention
• trying speed dating
• doing activities you used to love as a kid but haven’t done in many ears
• chatting with total strangers in an online chat room
• going to a nude beach
• trying new sexual activities you’ve never tried before
• going to a Meetup
• starting a new Meetup
• going to a few events where you know you won’t know anyone and challenging yourself to have a certain number of conversations
• doing the “20 questions to fall in love” with your romantic partner or with someone you don’t know well
• imagining what sort of person you’d most like to be and then act as though you have that personality for a day
• purposely doing five kind things for five different people in one day
• going to a store and trying on clothes that you wouldn’t normally try on
• calling someone who you haven’t talked to in many years
• becoming a “big brother” or “big sister” or mentor for a young adult or child
• starting ten conversations with strangers in one day (who seem open to conversation, without forcing them to talk to you)

Health

1. If you don’t like exercise, instead of forcing or avoiding it, find ways to make it fun so that you actually want to do it (e.g., find a different type , such as a sport that engages you, or allow yourself to watch your favorite TV show or listen to your favorite podcast only while you’re exercising, etc.).
2. Sleep is invaluable to our health and worth improving! Through experimentation, find the best combination of conditions ( e.g. eye mask/no eye mask, earplugs/no earplugs, blackout curtains/no blackout curtains, pillow thickness, room temperature, pre-sleep routine, and mattress type) that are best for you.
3. When you’re considering taking medicine or undergoing an important treatment, combine your own research with that of a doctor (in other words, don’t assume that you can figure out more than your doctor knows, you probably can’t, but also don’t assume your doctor will tell you everything you would want to know, or that your doctor has read all the latest randomized controlled trials). Read scientific papers on your own, but be sure to discuss the information with your doctor to gain a full understanding.
4. It’s a lot easier to eat healthy if you incorporate it into your routine (e.g., every day for lunch, eat a salad and only stock healthy snacks at home) than if you have to make a decision each day between the healthy option and unhealthy option

Socializing

1. Avoid spending time with bad people (whether bad influences, immoral people, or destructive people).
2. Organize group activities (at least occasionally) so that you can still see friends when life gets busy, and so that your friends get to know each other.
3. Channel your warm feelings for those you care about when you greet them so that they can viscerally tell you value them.
4. Be warm and friendly at the start of emails (even really short emails), because otherwise, some people will think you’re curt or demanding.
5. If you meet someone at an event who you’d like to see again, show initiative in following up with them, rather than waiting for them to follow up with you. Relatedly, it’s better to ask for business cards for valuable contacts so you can initiate follow up communication, rather than to just to give your card and hope they get in touch.
6. Be conscious about how you allocate time between social events with strangers and quality time with current friends or acquaintances. Try to figure out what your own ideal balance is, between the two.
7. It’s possible to find something of mutual interest in almost any interaction. The key skill is to ask questions to discover which of the things you’d enjoy talking about or hearing about that would be interesting or exciting to the other person as well.
8. When someone makes a great point or says something really interesting or funny, tell them that you enjoyed what they said!

Fun

1. Adventure is more often intentional than accidental. They typically involve adopting a mindset of openness and being on the lookout for novel opportunities that present a challenge.
2. Try new things regularly and shake up your routine, even if you’re not sure what to expect. It could lead to amazing experiences or a new life long hobby. Either way, you learn more about yourself, make your life richer, and avoid ruts.
3. It’s easy as an adult to stop having “play” where you do something creative or wacky or funny just for the joy of it, but forgetting how to play is actually a huge loss.

Work (much of this list applies mainly for work done at a computer since that’s the sort of work I do)

1. If you are serious about making a long term project succeed, get another person involved in some capacity (this could be a cofounder, but not necessarily). You should involve someone else even if the other person has a more limited role than you.
2. Figure out how to make your work environment as comfortable and non-distracting as you can; it is well worth the investment (e.g., get the right headphones, office chair or standing desk, computer, beverage access, room temperature, and internet setup, set expectations with colleagues for how often you’ll be available, turn off the distracting computer and phone notifications, etc.).
3. Each week, schedule at least a few uninterrupted blocks of free work time (>2 hours per block ideally) to use to work on those “high context” projects that can’t be effectively worked on in 30-minute increments.
4. Ask the people you work with what you can do to improve (and emphasize your determination to improve and need for honest feedback) even if there is no formal review process at your job.
5. Always invest time in learning new skills or knowledge related to your work (and beware when you’ve been at a job for a year and feel like you’ve scarcely learned a new thing).
6. If you manage people, ask them periodically how you could help them more or support them more in their work, and what is most frustrating to them or blocking them.
7. When networking (e.g., at an event), there are lots of people to meet, so if you’re not naturally connecting with someone, just move on to someone else that you connect with more naturally, don’t force connection.
8. The way to really make a positive impression when networking is to add genuine value to the people you meet, so be on the lookout for how to you can create value (sometimes a low effort action on your part can really help another person).
9. Be wary of introducing people to each other just because they work in the same industry (or have some other surface-level commonality); usually, people in an industry know a lot of others in that industry already, so that kind of introduction is not usually valuable and in fact can waste everyone’s time.