On Being 30: 10 Things I’d Tell Myself 10 Years Ago

People often refer to their grade school years as their formative years as if somehow the clock stops at 18 and then you are who you are for the rest of your life.

But that’s not how it really works. The formative years never end. You keep learning and growing for the rest of your life.

Who I am today at age 30 is radically different than who I was at age 18 or even age 25. In many ways I feel like the things I’ve learned most relevant to my life today I didn’t even start learning until my mid-20s.

At some point we all look back and think, “if I only knew then what I knew now.” Of course being a man, those things are colored from the male perspective for me.

Here are the best of the best from the past decade.

About Women

I’ll start here, because young men at the age of 20 think about nothing as much as they think about women.

1. It’s really easy to tell when women are interested in you.

If someone could have told me only one thing at the age of 20 that would have made life so much easier, this would be it.

When girls are interested in you they magically show up nearby you even when there is no reason for them to be around and their friends are on the other side of the room. They may not strike up a conversation, but you will notice that they wind up in conspicuously close proximity (you probably notice yourself doing this too).

If you’re talking to a girl and she flips her hair or tilts her head to the side exposing her neck, that’s also a pretty obvious and common indicator of interest.

There are many other ways women show interest without directly saying it, and most of them are pretty obvious if you can get out of your own head enough to pay attention.

Especially looking back at my early 20s, there are so many missed opportunities that I was oblivious to at the time that are completely obvious to me now.

2. Own your want.

I think most men have experienced some variety of this situation:

Her: Are you hitting on me?
You: What? No, how could you think that.

If you had a chance with her, you don’t anymore.

Maybe next time try “Yes, I think you’re sexy and I want to take you home tonight.”

Being so forward might take her aback and the interaction still might not go anywhere, but you will feel a hell of a lot better being honest about your intentions–and she will still respect you more than if you tuck tail and run.

If you have a particular interest in women, own that too. I’ve always had a fondness for Asian women. I find them all kinds of sexy. But when I was in college I worried needlessly about being labeled as “just another white guy with an Asian fetish.”

You don’t have to start every conversation with “you know what, I like Asian girls,” or whatever your particular taste is, but if someone calls you on it you can just calmly respond with a “yes, yes I do like Asian girls.”

3. Trying to make women feel comfortable doesn’t work.

On a related note, trying to “make women feel comfortable” doesn’t work. We men often try to hide our want and our true intentions to make a woman feel comfortable and like there is less of a sexual threat being around us.

The irony is that the very thing you are trying to do to make a woman feel comfortable–hide your romantic intentions–is what makes women feel uncomfortable and think you are creepy.

If you’re a man, stop doing that. If you’re a woman, realize where the behavior is really coming from and give him a break.

4. Choose relationships that work for you.

Here, honesty comes into play again. Honesty to yourself about what it is you truly want.

We go into relationships thinking that we have to find “the one,” fall madly in love, get married, move to the suburbs, and then have 2.5 babies.

You might genuinely want that, and that’s fine.

However, you might be at a place in your life where that’s not for you. If you’re a college student or just got out of a long relationship, you might not be ready to jump right back on the marriage track. Or maybe you do want to get married, but don’t want kids. Or maybe you have some particular fetish that you want your woman to participate in with you. The possibilities are endless.

If you show up to women telling them what you think they want to hear, you will attract women who want what you are advertising–and you will disappoint them when you don’t deliver. You will completely miss out on all the women who want the type of relationship that you want.

Be honest about your true wants and intentions and you will naturally attract women into your life who want the same thing.

About Work

College is a huge joke when it comes to preparing people for the working world. It doesn’t really matter where you go, I went to Stanford and was still pretty clueless when I graduated.

A few simple things known upfront can put you on the right track or help you correct course.

5. There are really only 4 different types of jobs.

Selling stuff – This includes sales & marketing. Your job is to convince people to buy things either in person or through advertising campaigns. If you’re in a non-profit it might be “selling” donors on contributing money.

Hint: These jobs pay the most money.

Buying stuff – Your company doesn’t just sell, it also needs to buy things. Your job is to negotiate contracts to get the right supplies and the right prices.

Making stuff – Software, computer parts, art, books, furniture, real estate appraisals, your job is to make something or provide a service. It may seem unfair to lump all these seemingly unrelated disciplines together, but at the end of the day they are all tied together in that they are producing whatever product it is to be bought and sold.

Crunching numbers – All the buying and selling creates mountains of data that someone needs to sift through and determine how the company is actually performing and give some indications as to what it should do next. Your job is making sense of the data and communicating it in a digestible format to the rest of the company.

Hint: College overwhelmingly prepares people for these types of jobs, but they are among the least satisfying and receive the least recognition (and are often not paid well either).

These four categories are a bit of an over-generalization, but if you look at any job you will see elements of these categories present.

Some of the most successful people–especially internet entrepreneurs–are good at or at least competent in all four areas.

6. Quietly let work you don’t want to do go undone.

I feel like this is one of the dirtiest, yet most powerful secrets I don’t want to give up.

Many, many projects get proposed in a business. Most of them aren’t any good. Many of them are just random thoughts without any serious intentions behind them.

When new projects are suggested that seem like a waste of time or are obviously bad ideas, it’s really tempting to put your 2 cents in to try and stop them dead in their tracks. If you do this too often you get a reputation as a negative nelly and an uncooperative worker (or an asshole boss depending on how you fit into the hierarchy).

The fact is, most of these suggestions will die as quickly as the breath they were spoken in. All you have to do is not take action on them, and they will go no further. You don’t have to ruffle people’s feathers by constantly shooting down their ideas.

However, if your boss, co-workers, or employees seem like they are going to insist on a project that you really believe is a bad idea then it is appropriate to address your concerns and convince them otherwise. If you are still overruled despite your most persuasive efforts, just go along with it and do your job competently.

That’s not to say that if you don’t like your job you should just quietly stop doing it. All work involves doing something you don’t want to do at some point or another. If you really hate all aspects of your job, find a new one.

7. Know your real objectives.

If you’re an employee you undoubtedly have some kind of performance review. If you’re an entrepreneur you undoubtedly have some vision for where you want the business to go.

At my first real job out of school I was paid a quarterly bonus based primarily off of two factors–revenue and profit for my book of advertising accounts.

However, during the course of the job I was given many, many projects to do. And much like in the movie Office Space, I had 10 or more people who thought they were my boss and wanted their TPS reports.

I fervently worked on these projects, often until 8 or 10 at night. Often being the last person in the office. However, most of it was busywork that was a complete and total waste of time.

Why? Because these projects did not contribute to either 1) more revenue or 2) more profit which were the goals I was being measured against.

In business you will have many competing interests on your time. All of them urgent, but not all of them equally important. You don’t have time to do them all. You will have to let many of them die or go undone.

As loud as that failing salesperson screams about his account that will generate $100 per month, you have to prioritize serving the accounts making $100,000 per month. If you don’t have time to service that $100 per month account, tough shit. It doesn’t contribute anything meaningful to your objectives and it robs you of your own personal free time–time that you will never get back.

Focus on the projects that move the needle and be prepared to let the rest die.

For bonus points, if you want to add rocket fuel to your career then know what your boss’s, boss’s boss’s, co-workers’, and customers’ true objectives are and help them get there.

About Social Skills

Sadly, charisma and social savvy are often viewed as “you’ve either got it or not.” However, it can be learned.

8. People are figure-outable.

We are taught that people are “irrational.” The hard sciences, math, and business are figure-outable, but not people. People are irrational, crazy, unpredictable creatures.

One of the greatest discoveries of my 20s is that this is not really true. People are far more predictable than they would like to believe. People are generally concerned with the same things: looking good at work, looking good in front of the opposite sex, and pursuing interests that they find meaningful.

People also generally have a sense of “what they believe” or “how the world should be” and judge everything through that lense.

If you simply pay attention, people reveal all of this information to you very readily. A hot girl walks in the room and all the sudden your buddy starts acting macho. Your neighbor who attends church every Wednesday and Sunday is–surprise, surprise–pro-life and very conservative about sex.

If I could make one change to school curriculums it would be to make psychology and sociology courses mandatory. Forget chemistry, nothing, and I mean nothing, will have as dramatic an impact on your life and level of happiness as your skill in interacting with other people and the fulfillment you derive from personal relationships.

9. Speak the moment.

I was a quiet kid growing up. Many people still mistake me as being an introvert, which couldn’t be further from the truth. In spirit I’m a diehard extrovert. I don’t crave alone-ness. I prefer an evening of good conversation to an evening of basking in solitude anyday.

People often asked me why I was so quiet, to which I could only respond “I don’t have anything to say.”

This “not knowing what to say” was seemingly an unconquerable problem. Other people seemed to be constantly commenting on this and that to no purpose whatsoever. And the crowd seemed to be generally entertained by hearing it. It just didn’t make any sense.

In my mid-20s I began to observe myself noticing things and wanting to comment on them. Then the moment would pass, and soon a whole evening would pass and I hadn’t said much.

I started making an effort to simply say my comment whenever it came to mind. It doesn’t even need to be particularly profound or important. Even something as simple as “Hey, look how big that dog is!” will do.

I call this “speaking the moment.”

When you get better at observing people, it’s especially fun to call them out on things you notice them doing. “When you’re done checking that girl out I’ve got a question for you.”

It’s also fun to intentionally misinterpret behavior. If you’re arguing about something with someone and a third person is there, “see, he agrees with me, did you see the way he twitched just now.” Or if there’s a girl nearby, “hey, are you just going to keep staring at me like a piece of meat or are you going to come over and talk to me?”

Note that it’s important to be fun and playful when you call people out in these ways.

So if you don’t know what to say, simply speak the moment and get yourself into the conversation.

10. Similar values are the basis of friendships.

Making friends is undeniably harder once you’ve left school.

You just don’t form the same bonds with co-workers and business associates that you do with classmates. And you just don’t have as much time to spend getting to know people on a purely social basis.

If you move around every 2 years like I do it makes it even more difficult because you are constantly starting from scratch.

The biggest shortcut to finding people who you enjoy spending time with is to find people with similar values. Forget going to the bar, find the local club of people who are interested in what you are interested in. Odds are that you will find that you share values across many more areas than just that particular hobby or interest.

Of course one of the tricks here is to actually know what your values are to begin with. Don’t get too hung up on that though. Values change over a lifetime. If they don’t you aren’t really taking an honest look at yourself and your life.

Just go participate in anything you think you might be interested in. Are you an atheist? Go find the local atheist meetup. Internet marketer? Hit the local internet marketing group. Paleo dieter? There are more and more local clubs for that too. Meetup.com is a great resource for finding interest groups.

Friends don’t, and most likely won’t, fulfill all of your social wants in the same person. It’s okay to have different friends for different things. Your hunting buddies might have no interest in tea club, and visa-versa. But there’s no reason you can’t be interested in both and have friends on both sides of the equation.

For bonus points, make sure that your romantic relationships also involve shared values.