1.
26 pieces of unsolicited and
totally obvious career advice to
make you more successful and
happier at work and in life.

2.
1) Figure out what you want.
And what you don’t. When you’re starting out, it’s beneficial to be get exposure to a bunch of different things. Startups
are a great place to be a generalist and wear a lot of sombreros. You get to pick and mix noncommittally. Staying in a
generalist role for too long will slow your growth and blur the line of sight to where and how you add value. Lack of clarity
can lead to bad decisions made by you or your boss and square peg round hole scenarios. No one will tell you what
you want, they’ll tell you what they want and/or what they think about you from limited interactions with you. Remember
that you’re in the driver seat - you solely determine your route, pace, company and music selection.

3.
2) Do stuff.
I go through cycles of knowing exactly what I need to do next and running after it and figuring out what I need to do next.
That figuring out phase is heavy on doing and light on sitting around waiting to be told what to do next or watching paint
dry. You can look for ideas externally, but most come up on the job while doing stuff. The more and harder reps you
get in, the more you see patterns emerge that indicate problems you need to solve and opportunities you
should take. When you spend too much time thinking about what to focus on next without just giving your all to doing
the work, you’ll miss the obvious and focus on the extraneous.

4.
3) Know what to focus on.
This applies to your core role and side projects. If you don’t know what the priorities are, ask for clarity. “I have a
lot of work to do, and want to make sure I’m focusing on things that will make the biggest possible positive impact on
the organization. What are our top priorities/goals? Can I run my priorities past you for feedback?” Passion projects at
work die if you create them to fulfill a perceived extrinsic need without vetting that need to make sure it’s a thing. Either
do it because you’re pumped about it and you see how it adds value regardless of applause, or because it is directly
aligned with a top priority.

5.
4) Assume positive intent.
Things that you care about will fall between the cracks. People will do things that piss you off or appear to intentionally
discount your feelings. Lines of communication will cross and you’ll feel like you’re getting blamed for something totally
outside of your control. When this happens, give it 5 minutes before reacting. Assume benevolence unless you
have good reason not to. And when you do respond, start with the end goal of the conversation in mind,
not your feelings. If you don’t, your feelings will sh*t on your desired outcome.

6.
5) Demonstrate mastery.
Your job is probably 100 moving parts. Are all parts essential parts of the machine, or are some more important and/or
higher leverage than others? Very few people are amazing at 100% of their job. I’m not. Demonstrate
mastery in the most important areas. If you’re good enough, other areas can be improved upon gradually,
outsourced or automated. You demonstrate mastery through consistency, process, being able to teach someone else
how to do what you do, and understanding what you don’t know to ask questions to continuously improve.

7.
6) Run towards problems.
Do you need to give feedback to another team member? Is a customer unhappy because of something we/you did?
No one wants to be on cleanup duty after the sh*t hits the fan. It’s the best learning opportunity though,
and watching/learning isn’t as valuable as doing. When you get sh*t on your hands, your more likely to care
about not getting sh*t on your hands again. Who sh*ts around fans, anyways?

8.
7) Fail, learn, do better.
Related: stuff isn’t going to go well. You’re going to have weeks that feel like playing Minesweeper blindfolded. Does
anyone even know what that is anymore? Failure is painful, but it isn’t bad. If you try to avoid it, your growth
will inch forward or stall out entirely. And isn’t that why you’re reading this article? All failure is good for growth - if
you seize the opportunity. Reflect on every failure out loud to distill what you’ve learned for yourself and potentially, your
team. Failing keeps you humble and, if handles well, creates the psychological safety to encourage other people to be
brave and try hard stuff.

9.
8) Help your boss let go.
Are you making your boss’s job easier or harder? Mark Cuban has said that the trait he values above all is an employee’s
ability to reduce her stress. Your job is to help your boss let go of the stuff that you’re doing, so they can go
to sleep at night knowing that you’ve got it. You’re focused on the right problems and can execute as well as if not
better than they could. Demonstrate ownership by acting consistently. Anything short of that and your boss will not let
go. Spending a ton of time talking about the routine stuff you’re doing in 1:1s signals a lack of confidence in your ability
to do the stuff you have to do. They don’t want more oversight, they want less.

10.
9) Learn everyday.
Improve continuously. Remembering how little you know keeps you open and aware. As you learn more, reevaluate your
tastes, preferences and world view. Learn, unlearn, relearn. One of the best ways to do this is to actively seek out new
learning opportunities by asking a ton of questions. Not asking questions or asking surface level questions
demonstrates a lack of preparedness and lack of awareness of how little you know. Ask better questions,
actively seek out specific information, learn intentionally.

11.
10) Don’t ask for permission.
Every company I’ve worked at, there’s frustration when someone gets chosen for a project or initiative. People that work
on fun/interesting special projects have usually previously demonstrated competence and confidence by taking the
initiative to identify a need and solve a problem. Once you’ve demonstrated mastery, experiment. Do new stuff.
Do harder stuff well. Leadership puts the majority of the straight edged puzzle pieces together but needs other
people to participate. Go puzzle.

12.
11) Develop your self awareness.
When you watch a talk show and someone tells their 1m story of woe, it’s clear what bad decisions and personality traits
led them to a life that consists of taking daily baths in creamed corn. When you’re in the creamed corn though,
everything seems kind of ok. Without self awareness, you’ll never get out of the tub (and you need to get out of the tub).
Self reviews are a great opportunity to develop this, but happen infrequently. Incorporate reflection into your work
day/week by reflecting on key activities to highlight what went well and why, and what you’d like to do
better next time. Positive framing makes building self awareness less scary.

13.
12) Ask for painfully direct feedback.
You will need help developing your self awareness. It’s weird to think that someone who you meet with for 30m a week
or month might know your areas of opportunity better than you do. They do. We all have blind spots. Ask for feedback
to find them. Most people won’t do this because it takes a lot of courage, and they carry their egos around
in shatterproof glass cases. The great thing about having someone tell you that something sucks and needs to
improve immediately prompts a faster response than saying that something could probably use some work.
Sugarcoating feedback makes it easily misinterpreted and creates little urgency to resolve.

14.
13) Seek out smarter people.
As humans, our inclination in social settings is to surround ourselves with sameness. Your peers, people who have had
similar experiences. Sameness gives you the foundation to build confidence and connection, but will not
help you improve. Look for an advocate who has been at the company for longer than you, is smarter than you
objectively/subjectively, and that you look up to and would want to trade places with. Listen, ask questions, and
collaborate with them when possible. Most tenured people want the opportunity to mentor. Teaching allows them to
deepen their expertise and confidence while getting the satisfaction of helping.

15.
14) Help other people.
The same, but mostly the opposite. You don’t have to go out and buy a mentor name tag. All you have to do
is pay attention. If you notice someone repeatedly asking questions within your area of expertise, offer to answer their
questions in real time. If you notice a bunch of someones repeatedly asking questions within your area of expertise, do a
training session, make a video or write something.

16.
15) Know when you’re out of your weight class.
I try to talk to someone outside of my network once a week to share ideas, to learn, to help. Last week, I spoke with
someone who has done a job similar to mine for much longer, and much better. So I STFU and asked questions. A
good way to piss off someone with more experience than you is to offer unsolicited solutions without
fully understanding the problem or what solutions have already been discussed behind the scenes. That
doesn’t mean you don’t have value to offer, simply that there is work required to have an opinion. Listen, learn, thank
them, stay connected to them.

17.
16) Don’t be a pain in the ass.
This sounds easier than it is. Your attitude impacts your brand, your relationships and the opportunities you’re given at
work. Being a pain in the *ss is different than being an *sshole, but can cause a similar fallout. Sort it out.

18.
17) Ask better questions.
Improve continuously. Remembering how little you know keeps you open and aware. As you learn more, reevaluate your
tastes, preferences and world view. Learn, unlearn, relearn. One of the best ways to do this is to actively seek out new
learning opportunities by asking a ton of questions. Not asking questions or asking surface level questions
demonstrates a lack of preparedness and awareness of how little you know. Ask better questions.

19.
18) Figure out what kind of job you want.
All work requires time and energy. How challenging the work is determines how much growth you get out of
your time and energy to continue to improve your career opportunities. Do you want a hard job or an easy job.
Easy jobs are at a minimum, stasis, and sometimes a step back. Hard jobs can feel the same because fear tells you that
you aren’t good now and, by some seriously flawed logic, that you never will be good. So you sit still and complain about
how hard it is, flailing wildly without making progress in any direction. If your job is hard, ask yourself if you’re willing to do
the hard work required to make it less hard and more fun. If not, why not?

20.
19) Do hard stuff well.
Related. This expands on doing stuff and running towards problems. You show irreplaceable value by doing things other
people couldn’t. Doing hard stuff will help you learn, and if you aren’t learning, what’s the point? Most of the
stuff that seems hard today will be easy with time and practice. Don’t expect anything to be easy without concerted
effort.

21.
20) Go where no one else has.
Just because everyone does something a certain way now doesn’t mean that it’s the best way. You have to learn the
rules first, but be skeptical. Constructively challenge the status quo to find new solutions for old problems, or find new
problems to solve. It’s easier to stand out through differentiation than through A+ sameness. Going where no one else
has demonstrates your fluid intelligence, your understanding of company values and priorities, and your ability to own
and innovate. Figure out how to paint by numbers, then Pollock everyone away.

22.
21) Don’t waste time worrying.
I’m a blind optimist. At my first job, I found out about a subset of the team’s general dislike of my repugnantly naive
upbeat ness from a foe turned friend ex coworker. If I’d acknowledged this pettiness at the time, I would have
succumbed to self doubt. Instead, I demonstrated my value and trustworthiness by doing good work and showing up for
my team. Worrying about what other people think is a waste of time. It will crush your confidence and get in the way of
doing your best work. It’s ok to give worry words, but always identify one step you can take towards putting that worry to
rest then go do it. Do instead of giving into the vortex of uncertainty.

23.
22) But don’t wait.
Ideally, imposter syndrome feeling keeps you humble enough to continuously improve. Sometimes, it tells you that you
are an imposter and you’re unwilling to do the work to feel like less of an imposter. If you feel like you’re wasting
your time or anyone else’s, you probably are. Confronting this takes bravery, but also frees you to move on to
something you can be great at.

24.
23) Set open ended goals.
Then create systems to achieve them. Eg. I want to be a better writer, so I’m going to read more/better writing, write
daily, and publish once a week. A path to a new world opens up in front of you when you intentionally reach for something.
You may not have clear goals at work, or be forced to set professional development goals. Set goals because you care
about your time on this planet and getting the most out of your at work experience. The goals other people set for you will
never be as powerful as the ones that you set for yourself, and the simple act of reaching exercises your ability to move
towards your potential.

25.
24) Solve more problems than you create.
Solving problems builds your organizational karma. Approach every problem with solutions in mind, and prevent/
solve future problems by routinely sharing what you’ve learned from mistakes/failures.

26.
25) Kick ass.
This is also harder than it sounds. We typically think that we are doing both better and worse than we actually are. Keep
your ego in check. Challenge yourself, create a plan for success, but don’t beat yourself up when you fail.
You contain multitudes.

27.
26) Give a sh*t.
This is the most important one of all. If you care, it will be obvious to everyone you work with. If you don’t, it will be
obvious too. Give a sh*t and everything else will fall into place over time. How fast or slow that happens is up to
you, and is directly correlated with how much of a sh*t you give.