Your goals are holding you back

This post was republished on Lifehacker.

I just started my junior year at Penn. Aside from a newly developed disdain for the freshmen I see bumbling their away around campus that is both terrifying and yet somehow familiar, there are a few things I’m bringing with me this September that I haven’t had in years past.

To be clear: I’m the first to recognize that I don’t have it all figured it out. I’m sure  there are plenty of 25 year olds that will read this piece and say, Man, wait until he gets out of college. Then he’ll really start to figure things out. I’m also sure that there are a plenty of 30 year olds that will want to tell those 25 year olds to shut up because life doesn’t really start until you’re married and have kids.

I’m still young, but I’m certainly old enough to remember being younger than I am now. And as far as I can tell, the only bar for being able to give advice is being old enough to remember your mistakes.

 One of the beautiful things about growing up is that I can look back on the versions of myself from years past and tell myself, Man, I was an idiot back then. I think that’s part of where my aforementioned disdain for freshmen comes from: I see a little bit of my former self in them.

When I got to college I had so many hidden insecurities, so many incorrect assumptions about the world, and so many questions about how to live I didn’t even know what the questions were. It was kind of like being dropped into an auto-shop and told to assemble a BMW from scratch. You’re given all the tools you need to do the job and you can look at already completed BMWs for reference, but the only thing that you can use to figure out what to do is trial and error. Needless to say, it’s difficult to determine where to even start.

I distinctly remember laying in bed at night about 5 days in to college and thinking, Holy shit what the fuck have I gotten myself in to. I don’t know how to live. I don’t know what to do. I don’t even know what kind of person I want to be. This is one big mess. But slowly, if you’re lucky, you calm down, make friends, and start doing more of what you love to do, which for me has, for as long as I can remember, been building products and writing.

There are a million little things that I can tell you about what I’ve learned thus far. Many of them are scattered in articles on this blog, and many of them will show up in future blog posts. But the biggest question that I’ve answered for myself, and I think the most important one, is this: How do I get good at something? What are the steps involved? What kind of questions should I ask? Where do I start?

There’s a lot of advice around on this particular topic. But I think what separates me from other people who have written about it before is this: I was a beginner so recently that I can still accurately remember what it feels like.

I remember seeing people building products, and getting them featured on blogs, and getting userbases, and giving speeches, and writing popular blog posts and feeling like I was seeing it all through a pane of impossibly thick glass: I could look but I couldn’t touch. I remember finishing a product and feeling like I didn’t even know where to start looking for people to show it to. It’s a lonely, vapid, discouraging feeling.  

I’m hardly a huge success yet, but I do have a thing or two to say about getting from zero to somewhere. I’ve built big userbases: WhereMyFriends.Be has about 40,000 signups. I’ve built and sold websites: DomainPolish.com. I’ve written popular blog posts: this blog has been visited by about 250,000 people this year. I’ve been in TechCrunch, Mashable, Inc., Time, Business Insider and others. I now have a network of entrepreneurs and investors that I talk to on a regular basis for advice. And I’ve done it all with no prior connections to anyone, while still in school.

I’m not saying any of this to brag. There are a million factors that have gone into that success that have very little to do with me. For example, I’ve been fortunate enough to work with some incredibly talented people my own age: Wesley, Ajay, Jesse, Justin, Patrick I’m looking at you. I’ve also been insanely lucky in some other completely unpredictable ways.

For example, blogging about my progress has been incredibly valuable. So has concentrating on building relationships with people I respect but don’t know by emailing them or tweeting them. But in my opinion, if that kind of advice were a dead horse it would already be beaten pretty thoroughly by now.

The only thing that I don’t think has been adequately addressed is building skill in the long term.

That’s what I’m going to talk about right now.

The advice from now on will assume that you know at a very high level what you like, what you’re passionate about, or where you want to go. Because that’s hardly a given, if you’re not there yet I suggest you read What Does It Mean To Love What You Do? and then come back.

Now back to the question at hand: how do you get good at something? Here are some common answers. I’m using coding as an example but this really applies to everything.

1. Set broad long-term goals and put time limits on them like “Get good at coding in the next 3 months”

2. Set specific short-term goals like “Do one coding exercise a day”

3. Be held publicly accountable by writing about your goals on your blog or having your friend hold you to them.

4. Keep track of how you’re doing every day so you always know where you are

5. Get a little better every day

6. Look for little tips and improvements or “hacks” for how to get better more quickly

All of these are self-help clichés. And they’re not wrong. In fact like all clichés, they contain a nugget of truth, but they’re too general to convey the subtlety required to become actionable advice. You can go from zero to somewhere using this advice, but I think it’s as likely to make you fail as it is to help you.

Why is that? The reason is because it puts emphasis on the results of what you’re doing, and relies entirely on your willpower to get you where you want to go. The reason this is dangerous is two-fold: your willpower is a finite resource and its availability is controlled to a large extent by your ego.

Your ego is a funny thing. It a lot of conceptions about who you are. It thinks you have all the talent in the world, and all the ability in world. It carries within it your precious self-image. The problem is that if your brain feels that your self-image is threatened it will shut down your willpower, and allow you to rationalize giving up in the interest of maintaining your ego.

This recognition helps us see why setting firm goals and keeping track of what you’re doing is a problem for beginners. It risks your self-image when it’s at its most vulnerable: when you’re trying something new. If during the first few days or weeks of coding you fail to reach a goal, either because your willpower is depleted or your goals were unrealistic, it’s easy to feel your self-image being threatened. Your fear center kicks in: what if I’m not as smart, and talented and special as I thought? And then it says to you: it’s better I stop trying than find out. And so your willpower is gone, and you’re right back where you started.

Setting goals and keeping track of your progress is putting the cart before the horse. It is certainly a part of getting better at what you do. BUT it’s not Step One in the process.

Oddly enough, in my experience, moving away from willpower-driven progress is more fun and helps you become more emotionally engaged in what you’re doing. Which produces better results, and allows you to maintain your rate of progress. So if setting goals is not Step One, then what is step one?

Step One is concentrating on habit creation.

In theory the idea is very simple: using tips and tricks, and keeping track of your progress, and improving every day are optimizations. They might make you 10% better, or 50% better, or even 1,000% better. But a 1,000% optimization on zero is still zero.

And so the biggest part of Step One is not to get better at doing, it’s to start doing.

In practice here’s how it plays out: this summer I decided I wanted to start working out again. I even wrote a blog post about it called Stop Taking Yourself So Seriously. Basically all I wanted to do was get to the gym once or twice a week whenever I felt like it, do a few things exercises and leave.

I did not: do research on the best exercises to do, buy expensive new workout sneakers, buy protein supplements to get bigger faster, set specific goals, or track my progress in any meaningful way. I just started going to the gym (in the middle of working 14 hours a day, 7 days a week on my startup).

While there I did exactly what I felt like. Sometimes I ran, sometimes I did arms, sometimes I did some legs. Whatever. If I felt like leaving early, I did.

And some weeks I didn’t even go at all.

What’s interesting is this: if I had set goals, and tracked my progress I would have been sorely disappointed at having missed going to the gym. I would have felt like such a failure. And my ego would have been very quick to tell me to just completely give up and rationalize it by saying things like: I’m too busy, or I don’t like exercising anyway. My willpower would have been sapped completely.

But none of that mattered to me. By just going every once in a while, and doing whatever I felt like doing the gym became a somewhat enjoyable experience. It wasn’t a highlight of my day but it certainly wasn’t horrible. Some days I even kind of wanted to go. And even more interestingly, having a week or two when I didn’t go at all had a surprising effect: it made me realize how much better I felt when I was working out.

That realization reinforced my emotional attachment to going to the gym, and I picked right back up with very little difficulty. It’s one thing to know rationally that going to the gym will help you feel better, it’s another thing to know it emotionally. And the emotional knowledge is the stuff that will help you to take action sustainably as a habit. Nobody just jumps in and goes to the gym 7 days a week. You build up to that slowly over a period of years.

Once you have enough experience at an activity like coding, something interesting happens. You begin to know: hey I can be pretty good at this. It might not get it at first, but I’ll be able to figure it out. That means you’ve successfully convinced yourself not to take your failures personally. Which means your ego is safe from being irreparably harmed, and your fear center won’t kick in to make you do weird things. Once you’ve developed that attitude, that’s when you need goals.

And that’s the point where I am. I’ve gotten good enough at a few things, and had enough little successes, to be intellectually and emotionally confident in my abilities. If I fail at something it’s because I’m not good enough right now, not because I’m not good enough. But even though I know I’m ready to set goals because they won’t threaten my ego, that’s not even where my concentration is.

I have long-term goals for this semester. But in order to follow them and eventually achieve them I need to get good at consistently keeping track of what they are and where I am in relation to them. And so the thing that I want to concentrate on the most this semester is a sort of meta goal: I want to habituate self-reflection and self-analysis of where I am in relation to my goals. My theory is that if I can do that, I’ll automatically start to get closer to achieving them.

So, in short to get good:

1. Learn how to build habits

2. Habituate doing the things that you want to get good at in an easy-going, non-threatening way. Recognize that this will take time.

3. Once you’ve done that, set goals.

Habituating doing what you want to get good at puts you so far in front of most people that by the time you start setting goals you’re already good enough to start making waves. As far as I can tell, the goals help you get from being 85% of the way to being good, to actually being skilled at what you do.

Like all advice, this particular flavor is anecdotal to my experience. If I’m actually making progress, I’ll be able to look back at this post a year from now and say, Man, I was an idiot back then. But I think that the core thesis of this approach will continue to ring true. The thing about experience is that rather than produce paradigm shifts in the way you think, it tends to help clarify, refine and contextualize ideas like this. I’ll let you know how things go.

You should follow me on Twitter at @danshipper. Or join the discussion on Hacker News.