How to Achieve Big Payoff Goals

‘And when Alexander saw the breadth of his domain he wept, for there were no more worlds to conquer.’
Hans Gruber, Die Hard [1].

Most of us will never be in the position of Alexander the Great (or Hans Gruber). There will always be worlds to conquer, and luckily that is the case, because there is an intrinsic human desire to grow, expand, improve and conquer new domains (Who doesn’t want to be master of their domain?).

A question I have always found fascinating is how do you translate this desire for achievement into results? There are many ways to think about it and I’d like to share with you my approach to answering this question. As background, I run a clinic where I have used this approach to help hundreds of people over the last nine years.

Cause and Effect

Actions determine results, right?

If I wanted to run the London marathon, it seems pretty obvious that following a proper training schedule is going to increase my chances of success compared to a regime based on drinking beer, smoking Cubans and being a Man vs. Food contestant.

Sure there might be a remote chance that even with good quality training, I might trip over and injure myself on the way to the start line or that aliens attack and destroy the planet Independence-Day-style the day before the race – but aside from the fickle hand of fate, if I follow the process I drastically increase my chances of success.

But actually even without taking into account luck, life isn’t as straightforward as actions = results. The fact is in some cases, even if you know exactly what to do, it’s still quite hard to follow the advice.

Consider a shy junior executive whose mentor suggests that he needs to attend more industry events to schmooze and grow his network.

Even when he is able to bring himself to attend an event, instead of gaining new contacts, he stands in the corner looking like a stalker who forgot to hide in the bushes outside.

Despite the mentor’s suggestion being relatively straightforward, it wasn’t that easy to put into practice. When you think about it, how many times have you received some advice you thought was worthwhile but still failed to act on it?

The point here is that we are inundated with books, blog posts, ancient alien prophecies, magazines, family members and friends giving us advice all the time, and yet even if it’s accurate we struggle to follow it.


Because changing behavior requires more than simply being told what to do. We are actually prisoners of our past conditioning. We have habits of thought and behavior that cause us to settle into a groove where we repeat the same actions over and over again.

And depending on the behaviors, to change these habits can be very, very difficult. It’s like turning around a large ice cream truck in a narrow alleyway.

The Truth About Changing Behavior

You may have heard the factoid that it takes 21 days to change a habit. This is rubbish.

There is no set time for how long it takes to change a habit. There are so many variables that affect it. It depends on what the habit is, as well as the person trying to change. Simple habits like flossing may be quite quick to change, while more complicated ones take much longer.

But in this article I’m not going to be talking about singular habits like flossing, making your bed or eating more root vegetables. I want to focus on bigger things.

We want to think in terms of the biggest (not necessarily financial) payoff. What goal can you work on that would have the most significant impact? We’re talking life-changing.

If it’s a sufficiently big goal it will invariably be made up of a web of different actions and behaviors. This means it’s complicated and difficult. You’re going to take longer than 21 days to achieve it. It could take months, a year or even more. You’re going to have to put in a lot of planning and effort. This is not for the half-hearted.

That’s why the payoff needs to be significant and worthwhile or else you won’t have the necessary motivation to follow through.

Possible Goals

Here are some examples of big payoff goals:

– Taking your startup from kitchen table to IPO

– Writing a best-selling book

– Improving your work performance and reputation to put your career on the fast track

– Losing weight (in a sustainable way)

– Improving your ability to produce high value work

– Finding a single woman to date in Denver (“Menver”)

– Starting up a popular new blog

– Improving your personal brand and image and changing the signals you send to others

– Developing the mindset to be a successful investor

– Becoming the next Martin Scorsese or Michael Bay

As you can probably see, each of these goals is made up of a lot of different actions and behaviors. Some of the actions involved will be straightforward while others will require changing long-standing habits.

To make your goals a reality, here are 6 elements I’ve found to be important when pursuing a big payoff goal.

1. The Desperation Dividend

It goes without saying you need to be motivated to achieve a big goal. But in my experience motivation isn’t quite enough for the majority of people. What I’m looking for is a sense of desperation.

Now I need to clarify my use of this word because it has a lot of negative connotations. I don’t mean desperation in terms of neediness. Instead I define desperation as “wanting to avoid a negative outcome so badly that you will do more than a regular person would do to achieve a goal”.

Let’s break that definition down some more.

I have generally found that for most people, the negative (and the fear of the negative) to be a much more powerful motivator than the desire for positive outcomes, especially in the initial stages of pursuing a goal.

For example, a woman might be putting off finding a new job and breaking up with her deadbeat boyfriend until she finds out that her worst enemy is now not only the CEO of a $10 million company but also dating Benn Affleck (the periodontist, not the actor).

Similarly, Luke Skywalker was quite enthusiastic about rescuing Princess Leia, but probably wasn’t going to do anything about it. It wasn’t until the the Imperial troops char-broiled his aunt and uncle that he had the motivation to actually leave Tatooine.

When I meet a client who is miserable and desolate about their predicament, while I definitely sympathize with them and give them looks of appropriate concern, I am also excited for them. Because here is someone who has nothing to lose. At this point, they are fully willing to get out of their comfort zone and discard the unhelpful beliefs and habits that had been holding them back.

This willingness to free themselves from the past is so crucial for making significant changes to your behavior. What this shows is that although it’s never pleasant to go through adversity, when it comes to pursuing a grand goal, there is perhaps no greater gift.

No matter what?

The other part of that definition of desperation covers the lengths you would go to achieve the goal. We tend to think of doing “no matter what” as being the pinnacle of commitment.

I tend to find “no matter what” as a potential harbinger of bad decisions, unethical behavior and possible criminal activity. On the other hand “doing more than a regular person would do” still puts you in a select group (since most people do almost nothing and give up after no time) and is a less crazed version of desire and motivation.

What if you’re not motivated to the degree of desperation? I would suggest you don’t start yet. Keep immersing yourself in the problem and your predicament[2]. Over time, as you wallow in it more and more, hopefully something will snap in your mind and then you’re ready to go . If that point doesn’t come, then you can still try for the goal, but in my experience it’s going to be much, much harder to stick with it through the inevitable challenges that lie ahead.

2. It’s Not the Goal That Matters

Read any self-improvement book from the last 30 years, and most of them will talk about the importance of goal setting.

I personally feel goal setting is over-rated. Talk is cheap. Anyone can make a big goal. My 12-year-old nephew recently told me he wants to be a multi-billionaire. So what? He will probably want to be an astronaut or Meryl Streep’s personal assistant next week. Anyone can set any goal they want.

But what distinguishes wishful thinking from a glorious reality is a concrete strategy and tactics:

– Breaking down a big goal into sub-goals
– Laying out plans for how to reach each of the sub-goals.

The problem with big goals is that while they may be motivating, they can also be very intimidating or overwhelming. This is why I always suggest pushing the ultimate goal into the background of your mind and focusing most of your day-to-day attention on the most immediate sub-goal.

As far as plans go, the reality is that, like Transformers sequels, most will fail. Because it’s hard, if not impossible, to predict the future. But this isn’t a problem because the purpose of planning is not to predict the future but just to make you think about it. It’s to make you think about potential challenges and obstacles, the actions needed to achieve the goal and the resources required to complete each step. Even if the plan is hopelessly wrong, the benefits of planning are worthwhile.

In other words, plans are good but goals are over-rated. Narrow focus on goals alone (and then hoping for some magic à la “The Secret” to bring them to fruition) is a mistake. Concrete plans win every time.

Include everything

Imagine that your friend Chuck who is a superb writer has decided to write the Great American novel. Unfortunately, while he’s good at writing, he’s terrible at promoting his books.

As Chuck plans out his novel, he has some fleeting thoughts about marketing. Given that this is not his strong suit, his natural inclination is to just avoid thinking about it. This is what most people will tend to do.

And so while he plans out his writing schedule in exquisite detail, he commits very little thought or time to marketing. His entire marketing plan consists of three pre-scheduled tweets (e.g. “Buy my new book #newbook”).

Six months after his book is published, unsurprisingly it’s languishing in obscurity; a masterpiece never to be discovered.

When you’re making a plan, you can’t miss things off that don’t appeal to you or that you don’t know how to do. Everything must be included.

But it’s difficult to do this on your own, because we can’t see our own blind spots (For instance, I presume it took a while for Bruce Willis’s agent to convince him to abandon his singing career). It’s much easier if someone objective can help you for this step.

3. The Pen is Mightier Than the Sword

What’s something that you can do in a few seconds a day that will seriously multiply your chances of reaching your goal?

That sounds like a sales pitch for a shoddy late-night infomercial product but what I’m thinking of is a genuine game-changer and yet so simple and easy: self-monitoring.

As we have discussed, with every goal there are certain actions or behaviors that are critical. Self-monitoring is the systematic observing and recording of the target behavior[2]. In other words writing things down.

Here are some examples of goals and the target behaviors involved:

– Losing weight: weighing yourself every day and keeping a food diary

– Pitching to investors: recording the number of practice pitches per week and pitches to investors per month.

– Getting a promotion: keeping track of the number of times per month you’ve walked the boss’s dog

– Improving work performance: writing down the number of minutes spent doing “deep work” every day

– Writing a novel: recording the number of words written and glasses of Scotch consumed per day

Self-monitoring is powerful because:

– You can track your progress

– It makes you constantly aware of your behavior

– You can spot patterns and behavioral triggers

– Awareness can help you improve your performance

Self-monitoring should not be difficult. In fact you should aim for it to be as easy as possible. Just figure out what you need to measure and write it down, anywhere: a notebook, on your phone, a crumpled up piece of paper, engraved on a stone tablet. Whatever it takes. Just write it down.

The most difficult thing about self-monitoring? It seems so simple and easy that you don’t bother doing it (or keep kidding yourself that you’ll start doing it tomorrow). Big mistake. I actually think it’s so important I will refuse to work with a client who is not willing to do this simple task, because it’s a strong sign of not taking the goal seriously.

4. Charlatans Miss This Step

How do you spot a charlatan? One indicator is when their advice doesn’t include any element of trial and error.

It’s a vain hope to believe that you will figure out the correct way of doing something the first time around. All progress on our planet (including evolution) has occurred through a process of trial and error.

Everyone is different and every situation is different. Even if I have done exactly the same thing that you are hoping to do, I am a different person, my situation is different and time has moved on since I did it. It is unlikely that the advice I give you will be instantly applicable (In fact often the advice of someone who has done it before is tainted if they insist that the only way to do it is the way they did it).

Any advice you receive (including this article) should be received through the filter of trial and error. It is only by trying something that you can see what works and what doesn’t and then modify it accordingly. Instead charlatans often present their advice as a one-off hit of brilliance that is supposed to sort out your goal immediately (e.g. “Come to this three day seminar and your business / work / startup / marketing / relationship / long-standing personality issues will be sorted out”).

The key points in trial and error are:

– Trials must be cheap – you don’t want to use Super Bowl commercials to figure out the right tone for your marketing

– Errors must be small and inconsequential – learning the tightrope 100 feet in the air without a safety net is not a place for trial and error.

– You need regular review to see what needs changing. Trial and error is definitely not “set and forget”.

Trial and error means that mistakes are good as long as they don’t sink you and as long as you can learn from them. With this approach the more you embrace trial and error in all areas of your life, the better.

5. The Answer is All Around You

A 22-slice-a-day pizza addict decides they want to lose weight. But there is one complication. They work as a pizza taste control officer at a pizza factory. Would you bet on their chances of success?

The external environment plays a crucial role in your likelihood of goal achievement and yet most people pay scant attention to it.

Your main aim with structuring your environment is:

Make it easy to make the right decision (and hard to make the wrong decision).

The amateur tries to use willpower. A bad nutritionist or personal trainer will tell you “just don’t eat chocolate” as if knowing that something was bad for you was enough to stop you doing it. Our minds don’t work that way. In fact, tell yourself not to do something and you’ll find yourself wanting to do it even more.

Instead, the better way is to use your mind’s natural laziness against it. For example if someone is trying to lose weight, the aim should be to make eating tempting food as inconvenient as possible. They could make a rule that they can have as much chocolate as they like but they have to drive to the store each time they want to eat a bar, and can only buy one bar at a time.

Similarly your environment should make it easy to do the right thing. For instance your environment heavily influences your work performance so you really shouldn’t leave it to chance.

Figure out basic things like:

– Are there certain physical environments that are better suited for certain tasks? For example, I prefer to do book or article writing in a quiet cafe than in my office.

– Are certain times of the day better suited to certain tasks? For example could you sort through your inbox while you’re asleep?

– Are there certain things you can do before and during a work session to make you more focused? For example going for a walk, working at a standing desk or taking industrial quantities of amphetamines (definitely not recommended).

In short, how can you engineer your workday for maximum alertness and concentration for the maximum amount of time (without the risks of burnout or substance dependence)? When you figure out your optimum work environment and style you can literally produce higher quality work in less time because you’ve found the right ingredients for mental flow.

It’s also worth noting that this is very personal and specific to each individual. Again, don’t listen to people telling you to only do things in one particular way. You need to use trial and error to figure out what works for you.

Time spent over a few months to find the right setup for you could possibly be one of the best investments you make, since it could easily mean doubling the amount of work you get done in a regular workweek.

All you need is the discipline to modify different variables in your environment and keep track of these each week, reviewing and making changes as needed. If you don’t have the discipline or bandwidth to ensure this gets done, pay someone else to help you.

Lastly, don’t neglect your social environment. Trying to achieve a goal while hanging out with a bunch of pessimistic losers is like trying to swim the English Channel with Hafþór Júlíus Björnsson strapped to your back. Don’t make things harder for yourself. Spend less time with people who aren’t where you want to be and more time with people who bring out the best in you.

6. The Unexpected is Expected

Do you have dreams of achieving your goal without any setbacks? On an unconscious level many people believe this is not just possible but expected. I know this because I see my client’s reactions to setbacks. Their emotions often range from shock to anger to despondence as if coming across an obstacle was utterly unexpected and unfair.

Let’s get this straight. It is completely unrealistic to expect to achieve a big payoff goal without many, many setbacks.

This means that

A. You should expect and accept setbacks
B. You should plan for what you will do when you encounter one.

I want you to think of setbacks like a Chinese takeaway order.

If you call up the restaurant and order a chicken chow mein to be delivered, when you hear a knock on the door you aren’t shocked or surprised. You don’t say “Noooooooooooooo!!!!!! How could this happen?!!?!” and then give up in disgust. Instead you think, “Ah, here it is” and answer the door. You expected it.

Same with setbacks. When something inevitably goes wrong, I want you to think of it like the expected knock on the door from the delivery driver: “Ah, here it is”. You knew it was coming. A setback is actually a sign that you’re making progress.

Something I’ve also noticed that clients find very useful is a “Setback Protocol”. This is a list of things you do when things go off track. Here are some things you could consider having in your own setback protocol:

– Speak to someone supportive

– Read or watch something inspirational as long as it’s not by Paolo Coelho

– Ahead of time, write down the reasons why you’re pursuing this goal – why it’s so important to you – and then revisit the list as needed

– Speak to someone who will help you to extract the lesson from the setback (there is always a lesson)

– Have a range of stress-busting activities like going to the gym, having a nap, watching a movie, having another nap or going for a walk

– Make a plan for how to overcome the setback.

– Resolve to keep going

Don’t be fooled by the rocks that I got

Think of the journey to the accomplishment of a goal as a path to the top of the mountain. And along the way at various points along the path, there are rocks blocking the road.

You can’t get to the top of the mountain without getting past those obstacles. They are an expected part of the journey so you have deal with them. In fact, if you never saw the rocks blocking the road, it would mean you had taken the wrong path.

And most importantly because you expected them, they’re not a surprise and you don’t turn back. You just find a way.

Conclusion: Think Bigger

Alexander the Great (and Hans Gruber) thought big. You should too.

Don’t waste your life away fussing over the small things, busying yourself with tasks that don’t matter and that don’t lead to anything significant.

Instead, find a big payoff goal that will truly change your life. Then do what most people don’t do. Take the goal seriously. Think about it and plan for how you will achieve it. Then focus your efforts, adjust your approach and persist through setbacks until you make it.

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1. Quoting Plutarch

2.This is consistent with the Transtheoretical Model of Behavior Change – and what to do in the pre-contemplative and contemplative stage.

3. Using Self-Monitoring: Implementation of Collaborative Empiricism in Cognitive-Behavioral Therapy

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