If you want to succeed, pick an easy target. If you want to improve, pick an impossibly hard target. Success in a goal and improvement are often opposite paths, so if you aren’t clear on which you’re trying to pursue, you may end up failing at both.
I have a habit for getting in over my head. I started this blog when I was 17, without qualifications or experience. I recently competed in several entrepreneurship competitions against MBA and PhD students, although I’m a 3rd-year undergraduate. Now, I’m going to live in a country where I don’t speak the language .
I’m mentioning this not to brag, but to point out that I was unsuccessful at almost all of these. This blog has had mild success, but that’s after three years of work, and I’m often surpassed by newer blogs such as Zen Habits , The Happiness Project  and The Art of Nonconformity . My team lost every entrepreneurship competition we attended. My first few months in France will probably be a complete butchering of their beautiful language.
I’m only mentioning a few cases, but the list of my failures is longer than the list of my accomplishments.
Improvement Comes from Failure
I set goals to be successful frequently. If I write a new e-book today, I have reasonable expectations of how much income it will generate. I usually try to innovate incrementally, so I learn a few things and improve each time.
But that is only an incremental improvement. If you want to make a leap in your abilities, you need to put yourself in an environment where you’re struggling to keep up. In those situations, success is unlikely, but you learn so much that your reach is much further for every other goal you set.
Choose: Achievable Success or Aggressive Learning
Don’t confuse success and improvement. Working towards success is a worthwhile goal, and it is often more rewarding. If your aim is to simply accomplish a goal within your abilities, that’s perfectly fine.
I’m starting a new writing project this week. My goal is to be successful, and to earn some additional income to pay the bills. I’ll learn incrementally, and I’m fine with that. I’m also setting a fitness goal to get back to my former weight of 160-170 lbs. I’d like to achieve this and see a boost in my fitness, but I don’t expect to have any tremendous gains in experience that will revolutionize my workouts.
You definitely shouldn’t set out to make the goal of every project a radical shift in learning. You need to pick and choose which goals you will set achievable goals for, and which you will force yourself into aggressive learning environments.
Placing Yourself in a Heavyweight Division
It’s not enough to set harder goals. That only makes failure more likely, it doesn’t mean you’ll work any harder or learn any more. If I set a goal to double my income in a year or double my income in a month, the latter doesn’t inspire me to do 12x the amount of work.
If you want to be a better boxer, you can’t just set higher training goals. You have to spar against tougher opponents. If you change the division you’re fighting in, your body’s defense mechanisms will kick in. A steep learning curve can’t be self-enforced, you need to be put in a context where it is forced upon you.
For my last eight months, my heavyweight division was competing in graduate-level new venture competitions. Our entire team lost a lot of sleep, failed consistently and continuously and had many moments of self-doubt and frustration. But, being pitted against people with far more experience and resources also allowed me to learn a tremendous amount.
I’m taking the same approach when learning to speak French. I’m working to improve my French skills incrementally during the next four months. However, I know that the true bulk of learning will come when I’m placed in an environment with native French speakers.
Finding Your Heavyweight Division
The key to radical improvements is your environment, not your personality or ambition. Psychological studies such as the Milgram Experiments  and the Stanford Prison Experiment  demonstrate the importance of context. In different contexts, the same people can be brave and heroic, or apathetic and small.
Finding an environment that will promote aggressive learning over short-term success isn’t always easy. But I think there are a few ways you can approach it:
- Surround yourself with the best people. If you associate with people better than yourself, the bar is significantly raised for performance.
- Dive into the deep end. Put yourself in a temporary situation that requires performance. Embarrassment, failure and losing isn’t the worst thing that can happen to you.
- Experiment with impossible tasks. Try something you’re 99% certain you’ll fail at. Sign up to speak in front of a crowd. Enroll in classes you don’t have the prerequisites for. Talk to the best looking woman in the bar.
Aggressive Learning and Burnout
Aggressive learning and mental overload are often intertwined. Success-oriented goal-setting may require work, but burnout isn’t a requirement. In aggressive learning, the entire point is to put yourself in a stressful situation so that you’ll be forced to perform. Aggressive learning is overwhelming because that’s the point.
Because stress and strain are high in aggressive learning environments, you need to take preventative measures to keep from being burned:
- Temporary. Aggressive learning is a sprint, not a marathon. Projects of 1-3 months are ideal because any longer than that and you probably won’t have the energy to continue.
- Time-Off. Take time off after a stressful project to focus on more achievable goals. This will help you recover and integrate what you’ve learned.
- Balance Stability with Aggression. Ramit Sethi has an excellent video  with Tim Ferriss where he discusses his philosophy of keeping stability in some areas of his life so he can be more aggressive in others. Aggressive learning works best if your life is already fairly stable.
I don’t think intensity should scare you. It’s just like weight training, where you undergo temporary strain accompanied by rest. If you balance it properly, the exercise should give you more energy towards the rest of your life by making you stronger in the face of discouragement, failure and frustration.