Why the strategy for reaching your biggest goals is not working, and how to make huge progress

How many goals or dreams have you set for yourself that you stopped chasing?

A lot of these you might not remember. Many dreams have been rinsed from your memory through selective thinking.

I hear a lot of people get excited about a new project; a big plan; a new business; a new book, or a new career. I often cringe when I see these same people years later going about life as if that dream never existed in the first place.

Charlene’s dream of writing a children’s book fizzled out after the first few scribbled sketches.

Jeoffrey’s excited commitment to building an iPhone games application startup lasted about three months before he realised it wasn’t for him, feeling better suited to hedge fund management.

Sam’s pop-up Italian catering service did well for two years, but excuses and a ‘loss of passion’ meant that her pop-ups stopped popping up and she went off to ‘find herself’ traveling.

There have been many dreams that I’ve personally stopped chasing which I was once excited about, from learning languages, to being a professional sportsman, to writing a work of science fiction, and beyond.

A lot of the time, we give ourselves really compelling reasons for ditching those dreams. Either that or they get replaced with other ones, or they get relegated to life’s more pressing day-to-day concerns.

Lack of focus was certainly a big reason behind the fizzling out of many of my own dreams.

Perhaps the idea that society shuns the idea of having dreams, your lofty goals, as unrealistic, selfish and even childish, has deterred you from pursuing them.

Many people, however, have seen their goals and dreams realised in spectacular fashion, even if their final success looked a lot different to their initial goal.

Having recently refreshed my idea of where I’m heading, it occurred to me that there is a problem with our traditional approach to setting major goals.

Don’t think that setting targets for yourself is misguided. It is not. Setting targets is very important if you are looking to move beyond an average life.

Setting particularly large ones is even better. Lots of studies have been done that you can easily find, which show we are switched on by bigger goals much more than we are by small to mid-sized ones.

You want to set goals that excite you and push your limits. Goals that are ‘nice’ are goals that you will not bother with. Goals need to be big, and they need to wake you the heck up when you think about them.

Nevertheless, there are glaring holes in most goal-setting strategies, small or large.

You’ll see, however, that it does not need to be complicated.

How many large goals have you set for yourself that you’ve actually reached, that manifested themselves exactly as you had planned? Try none?

That’s been the case for me anyway.

Beyond occasionally accomplishing small goals – which are effectively the same as to-do list tasks – I’ve rarely hit a major dream target that I had initially planned for.

I believe that major goals are attainable with a few tweaks in how we approach setting ourselves up to win.

The main reason we fail, in my opinion, is that we set ourselves up for inactivity rather than proactivity.

Staying proactive on a mission is all that counts.

The usual approach is having a main goal, but no plan on how to attain it. The goal is therefore never reached because we don’t have the clarity on what to do to get there.

If we do have the foresight to break our goals down into smaller goals, tasks, or steps, these steps inevitably get changed as we go along, and we lose sight of the main goal we set in the first place.

Either that or we fail to get motivated about each of the tasks we plan for, and the main goal fades into obscurity.

We need an approach to reaching our targets that does not lead to confusion, lack of motivation, and burnout.

My proposal is that we build on what we already know to work to get off our butts. Here’s how:

1. Decide on achieving something big, life-changing, and exciting.

For example: “I have a following of one million fans to my fiction writing by January 30th 2020.”


“I am a world renowned fine artist painter showing in galleries internationally, by September 30th 2022.”

2. Throw out the plan (don’t make one in the first place)

3. Make sure that the main goal is kept in mind through regular reminders, and commit to achieving it no matter what.

4. Make progress towards that goal through one-off challenges, or ‘games’ that we set for ourselves, many with a clear deadline.

The way I see it is that humans are not built to reach goals, they’re built to overcome challenges. As such, we want to be setting ourselves up to come alive in the face of challenge, not tedious ‘goals’.

These challenges should be things that test us over a short period – it could be days or months – in a way that excites us and motivates us to take it to completion.

For example: “Challenge #1: I write 1000 words of quality fiction every day without fail within 45 days, by [date]

I recently set myself the challenge of writing a full 100-page book for one of my courses (How to Get Illustration Clients) within a week.

Normally this is something that would take me months. Focusing solely on that project for that week, with no other distractions, knowing that I needed to prove to myself – if anyone – that it could be done, got me a major win in a very short time.

Compare this to when I spent nearly four months on a previous course for my book: ‘The Only Option’ of a similar length.

There was no solid deadline, no challenge to get it done, and my focus really suffered.

When you’ve completed that challenge, you assign yourself the next one-off challenge in alignment with your major goal.

This turns the whole process of achieving big things into something motivating, fun and ultimately, do-able.

Focusing only on one-off challenges rather than a large plan also has the profound benefit of keeping you focused on one thing at a time, making it vital that you think about what to prioritise as you move towards your main target.

You’ve experienced the equivalent of such challenges set for yourself or by others in the form of tight deadlines, at school say.

You might want to assign yourself more than one challenge at a time, in the pursuit of other goals (on a separate sheet of goals for your overall awareness), but it’s advisable to keep them to an absolute minimum, so that you maintain focus.

Such challenges would also be in addition to any daily work/tasks you’ve set yourself, such as daily meditation, or working on your craft.

Most of us will find this time-restriction highly motivating, even if it is at the last minute. We’ve seen how effective it can be.

It is this approach that make challenges work, especially those that push us out of our ‘zones of comfort’, to get you taking action.

In a nutshell, this whole process works to get you excited about steps you need to take in line with your big dream. It works because it sets ourselves up for activity and productivity rather than inactivity, which is so common in most strategies.

To add even more power to this strategy, you want to make these challenges very difficult to fail, psychologically. Apps like Stickk.com assign a monetary value to projects, tasks, or, in our case, challenges, so that your incentive to succeed is massively increased.

I’ve seen it work for myself and my clients such that I use Stickk for all my bigger self-imposed challenges (this is not an affiliate plug for Stickk).

If you have someone act as an accountability person to oversee whether you are doing the work or not in time – this makes it even more effective.

When going for your dreams, the worst thing you can do is set yourself a big goal, and then leave it at that. What makes all this flow smoothly to success is reminding yourself of your main goal everyday – absorbing it into your psyche so that it becomes part of you.

If at the end of your main dream deadline you’re not quite there, guess what, you likely made huge progress because your strategy was in maximising action towards a dream rather than mindless planning.

At this point you could extend your deadline, but only do this once you reach the end of your time limit so that you are pushed to get it done.

To summarise, most people fail to achieve the dream goals they set for themselves because they get stuck in planning and overwhelm. Dreams are after all huge undertakings in totality.

To make it work, my solution is to commit to a major goal, to ignore a breakdown plan, but to steer your way through one deadlined challenge after another, so that you take action in the right direction, and reach your dream.

As always, make sure you sign up to the newsletter for more like this, and other tips, and to leave a comment if you want to add to this discussion.





  1. Really great read Alex! I’ve never liked the idea of making a plan list or anything of the like as I understand that you can write these things down until your heart’s content, but it’s your action in the midst of the entrepreneurial rollercoaster ride that brings about the manifestation of your goals.

    What’s more is that the ‘dream trek’ is littered with hitches and occurrences that were simply not apart of the plan, so you run the risk of hampering your progress by sitting in despondency when things get inevitably get a little hazy. Goals are good, but grit is greater!

  2. Really needed this. I’m one to make small to medium goals and forget them after a while of finding something new. I’ve found that making a large project into smaller tasks has helped a lot more then just focussing on the tasks as a whole.

    I agree with what Dion Lynk said about grit being greater! We’ve got to be able to be strong and motivated to follow through with what it is we want to achieve.

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