Thoughts On Work

Status quo, you know, is Latin for: the mess we're in.

Ronald Reagan

These are just opinions.

These are just opinions. Take it with a huge grain of salt - this is my own experience, and the experience of a few people I know.

Happiness is not a state.

Happiness: an elusive feeling. People actually mean fulfillment. In other words: feeling like your work matters, that you matter. It means sustaining this feeling long-term, unshaken by day-to-day life.

We spend the majority of our life working. The average person spends 90,000 hours working in their lifetime.

Trading time for money is stupid if you don't enjoy the time you trade. How can you make it count?

People operate on planes of acceptance. They look for security in a job. If they can just get a high-paying job and secure their financial future, they will be content.

Once they get a taste of security for a few months, they start to feel bored. Here are some common reactions: consuming more, learning more, working more, worrying more. In searching for less, they somehow end up with more.

As they stay in the job for longer, they may start to get greedy. They want more, and they find ways to rationalize the decisions that they are yet to make (asking for a raise, leaving, finding a new job). This isn't wrong, it's natural, and it's why companies have excellent retention programs.

Most people ignore these uneasy feelings and attempt to live with them. These neglected emotions hurt us in invisible ways, and the worst part is: we could have used them. Emotions add more meaning to your life, suffering is a function of how you react to them.

You may find fulfillment in work, but it's doubtful you'll find it in your bank account.

I've outlined some working thoughts on this endeavor we call 'work'. If we have to toil away at something for most of our waking day, we should extract as much as possible out of it. I have some theories on how you might be able to achieve this.

Some of these theories illustrate forgotten truths: Your manager is an employee too. Some of these theories are a bit more prescriptive: Your emotions are tools. Some of these theories explore common pitfalls: Don't optimize in hindsight.

I hope these theories can help you make up your own mind.

Work better, not more.

As you progress, you will have less time and more expectations. Something needs to give. Will it be your hobbies, relationships, work performance?

Avoid stagnation.

What worked for you once doesn't work in perpetuity. You must keep learning and trying new things. If you feel mastery, that's usually a bad sign.

Your manager is an employee too.

Your manager is an employee too. They are subject to the same performance reviews that you are. If they aren't the founder, they are still accountable to a higher power, and they have to meet certain performance thresholds. Remember this any time you think of your manager as not understanding your predicament. They were in the trenches too.

• If your manager wants to keep you in your current position, they will ensure you don't get too big for your boots.
• If your manager needs you to grow into a new position, they will ensure you have all the resources and time you need to do so.
• If your manager doesn't care about their job, they will usually leave you alone to do your own thing, especially in bigger companies. Use your autonomy wisely.

Leverage makes everything easier.

If you have a problem with someone influential at work, leverage means you can stand up to them. Lack of leverage means you are at their whim. If you disagree with values or ethics in your workplace, leverage means you can give your honest opinion, unabated by worries about your promotion case. Here, leverage is the difference between being silenced and being heard.

Often, the people with the most leverage are not the ones who have constructive insights to give.

It only goes so far. Having leverage is the not the same as being leveraged. Overextending this privilege usually leads to negative outcomes. Leverage is like currency: spend it all and nobody can do business with you anymore. Your workplace is not a family and the love is not unconditional. If you run out of political capital, you lose.

The grass can be greener.

Throughout your life, people will tell you "the grass is not always greener" on the other side. Even more so when what you are doing is risky. For you to tell, you need to separate your life from your work: are the negative emotions you feel rooted in the work you do, or something else?

In other words: is it that bad? Only you can make the final call. The grass can be greener.

I had a job change that more than doubled my income, gave me great co-workers, and a brand name on my resume. I didn't have to sacrifice to gain a significant improvement.

When people gripe about their work situation, how much of it is about work? The people that proclaim happiness one day are often the same that gripe the next.

Your emotions are tools.

The banes of your existence: anxiety, fear, regret, are all immovable. You will not beat them. Give up. These feudal tyrants take up free real-estate in your mind, conspiring against you, petulant and quick to shut you down. The good news is that you are smarter than them. What do I suggest?

You have goals and ambitions, but your feelings don't. What if you gave goals or ambitions to these feelings? Think of yourself as a teacher, assigning homework to your pupils. Your job is not to crush them or ignore them. Your job is to redirect them towards what is most productive.

• Feeling anxious about a deadline? Redirect this anxiety into action and get the project done early.
• Feeling fear about a recession? Channel this fear into recession-proofing your career.
• Feeling regret about something you said to someone? Feel and display your regret. In other words: apologize.

In most of these situations, the worst thing you can do is be inactive. These tools were given to humans to compel action.

Don't optimize in hindsight.

Avoid "rationalizing" the past with information you have now. The reality is: you didn't know that startup was going to blow up. Comparisons are ugly, and everyone is guilty of this. When you feel a tinge of regret, sit and think about it for a second.

What's in your fantasy? Does the fantasy involve a lot of money? Does it involve big events and big raises? Or is it about those boring things, like team fit, day-to-day work, and all that other "junk".

I've done a lot of this fantasizing in the past, but I've realized something. Fulfillment never entered my thought process. I didn't think about team fit, my interest in the mission, or workload. My fantasy was about the glorious moments, not the grueling ones. Most companies are a total shit-show, especially startups. This doesn't mean that you shouldn't join a startup, but it does mean that those "boring" things need to be solid.

For most people, it's about money. Bigger stock grants, higher salaries, extravagant benefits. This is a poor and unexciting way to see life, but it's a trap many fall into and have to claw their way back out of.

We know you can't optimize in hindsight, but even if you could, are you optimizing for what you want? When you reach the end of your life, will you feel that much better about all the extra dollars you made?

The amount of conversations I had in San Francisco about salary were nauseating. It's even worse online (cough cough, Blind). It's not wrong to chat about money with your peers, but it's a shitty topic for small talk. Leave it for losers with too much money and ill-furnished apartments.

Money is great and you'll make plenty regardless. You can buy the things you want (except for private jets), but you can't buy back your time.

If you hate what you do and can't switch to a different career, you might as well start a company and profit more from it.

Beware working more.

Your reward for doing lots of work is more work. This effect usually increases as you go further down the chain.

• If an executive is assigning you work, and you complete it quickly: expect more work.
• If a direct co-worker is assigning you work, and you complete it quickly: expect some kudos.

If you're aiming for promotion, one successful project is better than a million useless edits. Successful means impactful to the business's bottom line, not that the change worked.

The more the person has an incentive to use you to further their goals, the more they will do so. This doesn't mean you should laze about. It means you should be more selective about what you work on.

Balance is a dirty word.

Jeff Bezos talks about "work-life harmony", and this is the best perspective I've found yet.

There are two polar ends of the spectrum: die-hard entrepreneurial archetypes that insist on working yourself into the ground, and "work-life balance" addicted coasters that drain value from their company and co-workers.

There's nothing wrong with either, but both lend themselves to imbalance. In the first, you may be so consumed that you cannot have a life outside of work. In the second, you may have so much time on your hands that you get bored.

The people who abhor laziness burn themselves out until they can't work anymore. The people who abhor working use "balance" as a codeword for: I hate 40+ hours of my week, please release me.

If you can find a balance between the two, you give yourself the opportunity to find fulfillment in both. A teammate said to me once: "the more senior you get, the more people will disrupt you, and something has to give". Will it be your health, will it be your time, will it be your fulfillment, or will it be your scope? These are all hard questions to answer, and the examples above are not absolutes. Your priorities will determine where you fall on this spectrum. To find balance, you need to be as honest as possible about your priorities.