7 Reasons You Might Not Be Reaching Your Creative Goals

When I first took the plunge and began my freelance creative career (at the time as a web designer) I had just one goal:

Make enough to pay my rent each month.

Not exactly ambitious, but it was a start. Having more control over my time and actions than I’d ever had in my life, initially felt exactly how I wanted: FREEING.

Why don't we reach our goals? Here are 7 tips for creatives >>

I loved being able to decide when to wake up, when to have breakfast, whether or not I should shower… That all lost it’s novelty quite quickly though.

It turns out: structure makes me happy. Having a routine meant less decisions and having something to shoot for, a challenging goal, kept me MOTIVATED.

Yep: I became a chronic GOAL SETTER.

I had goals for the year, for the decade, for the day… I had all the goals!

But when I realised I wasn’t actually reaching nearly any of these goals (at least the ones I remembered to keep track of) I had to take a long, hard look at what mistakes I might be making when setting these lofty goals.

What i’ve boiled it down to, are reasons that might affect creatives – small business owners, freelancers – in particular. Much of our work is intangible for a long time, before we can take action and make it real.

Our practises depend on inspiration, motivation, flow… we can’t just tell ourselves to get our butts to the track to work on our sprints, like an athlete might. We’re dependent on being ‘hit’ by that whack of insight that allows us to do our thing.

If you find yourself struggling with goals – setting them, sticking to them – I hope this post will be of some help in getting to the reasons why that might be, and help you correct course.

7 Reasons You Might Not Be Reaching Your Creative Goals

1. The goal isn’t specific enough

When we set vague, blurry goals they feel easier to reach than super specific goals.

For example, If I set a goal to ‘sell more paintings’ that sounds easier to achieve than ‘sell 10 paintings for X amount of money’ because when I set the latter: I know damn well if I’ve failed or not.

When you set a vague goal, you get vague – or non-existent – results. Be brave: set a specific goal.

2. The goal isn’t realistic

Whether you think you can, or you think you can’t: you’re right.

~ Henry Ford

As hackneyed as that old adage is, it’s damn true.

By all means we should challenge ourselves and set ambitious goals – but we still have to BELIEVE we can reach them.

For example, when I first set up my pet portraiture company, I thought I’d have customers as soon as the site went live.

What’s that? That would be the sound of CRICKETS. My confidence was shot, and my goals had to be readjusted very quickly.

When I did set more realistic goals, and started taking action, I started reaching them and getting my confidence back. There needs to be at least a shred of hope in attaining the goal, or we’ll quit at the first hurdle.

Henry Ford quote

3. The goal has no deadline

One thing I recommend is setting a multitude of deadlines – but I’ll get to that.

Having a time line, a schedule, is key to getting anything done. Some creatives might balk at this: the idea of having a rigid structure is something you might have wanted to escape by pursuing a creative career.

I was one of those people! It took some time, but I realised that without a deadline: I got nothing done. I would start setting my own deadlines, as arbitrary as they were because that was the only thing that motivated me some days.

Trello became my boss of to-do’s and deadlines. The ability to assign a due date to each task was a game changer: when a task doesn’t have one: it stays undone.

So try setting deadlines, even if they feel arbitrary at first.

Top Tip: It’s also easy to forget deadlines when no one’s on your case about them. If you need to: set a load of reminders, whether it’s on your phone, on your calendar, Post-it notes attached to your cat…

Cat post its

4. The goal isn’t snackable

The multiple goals I recommend creating I think of as ‘mile markers’. When you break a goal down into ‘snackable’ bite-size chunks, you can reach each in stages, whilst working towards the overall goal.

For example, if your big goal is getting your work in the trendiest boutique gift store in town, you could break it down into stages. One snackable chunk could be to go into the store this week and start getting friendly with the manager – or heck, the sales assistant.

The smaller the chunk, the more likely you are to actually try it. The big goal feels far less intimidating, and more manageable when we start breaking it down like this.

5. The goal isn’t measurable

What gets measured gets managed

~ Peter Drucker

Goals such as ‘paint more’ might be tricky because we don’t have a way to measure them. What is this ‘more’ you speak of?

In this case, our measurement unit could be time. The goal becomes ‘paint every Sunday and Wednesday evening for 2 hours’.

Top Tip: Use a habit-tracking app (I’m currently digging Productive) which allows you to keep track of when you hit the goal and when you don’t. There is something innately satisfying and rewarding about checking something off the list, after all.

Peter Drucker - What Gets Measured

6. You have no accountability

Gretchen Rubin has identified the ‘Four Tendencies’ of people in terms of how we form habits and get things done. I strongly recommend the book, Better Than Before (especially if you’re a habit-geek like me) but one thing that I took away from it was this:

If you’re an obliger – someone who is motivated by a feeling of responsibility to others – you will massively benefit from being held accountable by another person. (This is a great episode of Ruben’s podcast that dives into this tendency.)

I discovered many of the members of the League of Creative Introverts were obligers, and often felt they spent much of their time doing things for others – but struggled when it came to doing things just for themselves.

For those members, I knew an accountability buddying system would work fantastically. Each week or each fortnight, two buddies check in on each other. They can tell each other how they’re getting on with their current goal, share tips on sticking to their goals, and announce their goal for the following week.

League of Creative Introverts

For the rest of us, accountability might come from within (so using a habit tracking app can help) and for others: it’s actually best not to share your goals at all, according to Derek Sivers:

Experiment and see what works for you.

7. There is no margin for error

Never confuse a single defeat with a final defeat.

~ F. Scott Fitzgerald

You can nail all the previous tips and tricks I’ve shared here and still find: Crap. I didn’t reach the goal.

The next step? to give up entirely on the goal of course!

Er… not quite.

I’m an all-or-nothing type, so this one is what has made all the difference for me and my Type-A, perfectionist tendencies.

For example, if your goal is to email your press release out every day for a month, and you have a great run the first week, you’re on top of the world.

Then: you miss a day. You forget. Your dog gets sick.


Instead, you can reframe the goal so it becomes: “My goal is to email a press release at least 5 days a week” you’ve built in margin for error.

If you hit 7 days, you rock! If you hit 6, you still rock! Heck, if you hit 2, you still rock: as long as you pick it up again when you’re done looking after the dog.

F. Scott Fitzgerald quote



Tell me, do you struggle with reaching your creative goals?
Got any tips? Share in the comments below, or tweet @creativeintro


League of Creative Introverts