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How to Use Life’s Milestones to Achieve Your Writing Goals

By Donna Barker

I’d like to start by telling you three stories, which will explain how I came to the realization that milestones are one of the best ways to fire up your creative courage, confidence, and commitment, and for getting your book idea through all the stages of writing, editing, and self-publishing.

The first story starts three months before my 40th birthday. I’d spent a good deal of the last year of my thirties reflecting on what I’d accomplished in my career and life, and where I hoped to be in ten years. Overall, I was successful. Self-employed as a freelance writer working with clients I loved, making good money, having the freedom to take my son to school and pick him up each day.

The one area that I didn’t want to see myself in the same place was in how my marriage was functioning. My life transition from 39 to 40 prompted me to make a decision about that relationship that I’d have never even considered the year before.

The second story starts when my dad told me that he’d been diagnosed with Stage 4, non-small cell carcinoma. The prognosis was that he had less than six months to live. And, more to the point, he wanted my help achieving a lifetime goal he’d had: to write a book.

I’d already written and edited an entire manuscript before realizing that my first foray into writing fiction was a project that would forever live under my bed (since the story was really 100,000 well-edited therapy words about what happened to a ‘fictional’ character who found herself single and dating at age 40). But the themes that I addressed in that manuscript were ones I still wanted to write about. So, as way of support for my dad, we both set out to write a scrappy rough draft of our novels before the end of the year.

Sharing pages with each other and holding each other accountable, we both got our first 50,000 words written during NaNoWriMo 2012. I started the editing process and he kept writing until he had 110,000 words of a Tom Clancy-esque international espionage story.

I gave Dad notes and he started the revision process. But he’d started writing too late. And although he outlived the doctor’s prognosis, his health and energy levels kept him from completing the novel. He died having not quite achieved a goal he’d had for some forty years and it broke my heart.

I finished the edits for my own book and started to submit my story to agents and contests. Several agents asked for partial and full manuscripts, one agent reached out to say how much she was loving it. The story in manuscript form was a winner in the two contests I submitted to.

But what did I do when that agent who had the most interest ultimately declined to represent me? I gave up.

Which leads me to the third story, which took place exactly ten years after the first one, in the last few months right before my 50th birthday. After having let my fully edited manuscript sit for almost two full years, I decided that the risks involved in putting my book into the world would not be as devastating as the risk of dying, like my dad had, before I could call myself a published author. And so, I self-published. And that book, although it hasn’t made me millions, has changed my life.

The very act of having completed a life goal that over 80 per cent of us are said to have, but fewer than one per cent actually accomplish, changed me. It gave me a confidence in myself that has spilled into so many other areas of my life.

It took the milestone of being on the edge of a life transition to boot my butt into action.

Since I don’t believe that I am a special snowflake, I figured that my experience of having faced two-decade transitions and finding my life changed each time probably isn’t special to me.

I had this idea that since one milestone had enough power to make me rethink a relationship I’d thought would be forever, and the milestone my dad faced of his imminent death gave him the focus to write the story he’d been carrying with him for decades, and the milestone of my own you’re-not-getting-any-younger life transition helped to push me past the very real fear I had of indie publishing my book, that there was probably some science behind it.

Lo and behold, there is. Science has proven that milestones help us achieve personal goals. I was thrilled to find that two sets of studies confirm that my experience was consistent with others.


Dates and the meaning that we place on them have the power to help us change our habits and behaviours, but even more importantly, our beliefs about ourselves.

Research from business schools at NYU, UCLA, and the university of Pennsylvania, dive into the many habits that people start, the habits they break, when they make those commitments, and how successful they are in sustaining those new habits.

The most obvious milestone date is starting a new year. Most of us decide that we’re going to make a change in the following year to better ourselves. But statistics (and I suspect your own personal experience) show that the success rate for New Year’s Resolutions is woefully low.

So that sounds like it disproves the theory that dates can have an impact on our goal setting and achievement, right? Yes and no.

To understand how milestones have the power to help us achieve aspirational goals, we first need to separate the day that we feel compelled to start a new habit from our previous success or failure connecting that goal to that day.

Because here’s something else we know that plays into goal-setting success rates:

The more times you set a goal and fail to achieve it, the less likely it becomes that you will do what it takes to stick with it when a challenge pops up the next time you try.

You might be familiar with this experience. You tie a goal to a milestone date – like writing for at least fifteen minutes every day starting on January 1st. Something happens, and you miss a day. You’re disappointed with your lack of commitment but it was just one day so you recommit. Try and try again.

But then another thing comes up and you miss a few days in a row and at that point your brain “helpfully” reminds you that you’ve never been good at routines. You quietly stop trying and hope that anyone you told about your resolution will have forgotten, or have also failed with their goal, so won’t ask how you’re doing on yours. Sound familiar?

The problem really lies in tying your goals to a milestone date that has no special meaning to you. If you don’t have a personal reason to truly care about that day, then it’s really no different from any other in terms of its potential power to be a milestone date that will help you achieve your writing, or any other goals.

Instead of giving up on the power of using a milestone date to achieve your aspirational goal, try one of these approaches instead.


Find a start date that has real meaning to you.

If the first day of January is just another day to you, perhaps there’s another day that you feel more of a connection to in terms of making a fresh start. One of the reasons milestone start dates work for many people is that we effectively decide that the person we were before that special date, and the habits that old self engaged in, are not welcome or going to be carried into our new self. We consciously decide to make a fresh start and once we do so, it gives us permission to erase all those other attempts since that’s not the person we are anymore. It might sound silly, but it does work – when that fresh start date has meaning to us.

At an extreme we can see it in the way many people with addictions say they had to hit rock bottom before they could break old patterns. Their fresh start date is clean and meaningful. The person they were on the day they crashed is not the person they will become moving forward. They can tie all the bad behavior to the self that they’re leaving behind.

Some people tie fresh start behavior to milestone birth dates like 30, 40 and 50. Others, who have spent decades in post-secondary school, will find that Labor Day weekend, or the first of September works as an effective milestone to break old habits and set new ones. Religious and cultural dates are also powerful as fresh starts for many people – Easter, the lunar new year, Rosh Hashanah, Nowruz, and Diwali are a few.

The ‘trick’ to make a fresh start date work as a milestone to help you achieve an evasive goal, is to take the time to write down the behaviours and habits that you want to leave on the other side of that date with your former self. And then, when your old self sneaks in and reasserts his domain in your new self’s life, to consciously remind yourself that the unwanted habit or behavior was part of the you that you’ve outgrown. Don’t beat yourself up about resuming the old habit or dropping the new one, simply remember that your fresh start self has different goals and motivations.

And if that doesn’t sound like it resonates with you and your personality – you’re not off the hook. You can make a milestone date work for you from the success side of the goal.


Find an end date that has real meaning to you.

If there’s no date on the calendar that feels meaningful to you to set as a milestone start date, approach the milestone as your finish date. Evidence indicates that this backwards approach can be equally effective with helping create a fresh start.

To use this approach, start by figuring out your writing goal. Are you trying to finish your scrappy rough draft, or are you trying to get twenty ARC readers so you have reviews when you indie publish? Or is your goal something in between?

Write that goal down.

Your next step is to figure out what event in your life or world can be legitimately connected to that goal. For instance, you’re attending a writer’s conference in six months and you want to have a polished draft ready to workshop. The conference becomes your milestone.

Or your 25th high school reunion is coming up and you want to be able to show those people who mocked your poem in Grade 12 English that you are, and have always been, a writer, by proudly declaring that you are an author on your name tag. The reunion is your milestone.

Or your own nine-ending birthday is on the horizon, and darn-it-all, that was the decade you started this book and you’re not going to end it with unfinished business.

Write down as many dates and events that have meaning to you that you could tie to your book goal.

Now go back to your original goal and see if you can make it line up with a meaningful-to-you date. If your school reunion is in three weeks that date won’t work for a goal unless it’s simply to hit Publish on Amazon with a book that’s already good and done.

Figure out what you can get done by your meaningful date that will move you closer to the big goal of being a published author. Or, find a different meaningful date to connect to the goal you stated in step one.

Basically, since you’re tying your goal to a finish date instead of a start date, you may need to do some back-and-forth with the two parts of the equation. If there’s a milestone date that feels really important, adjust your goal to have something significant accomplished by that date. If your goal is something you cannot change, then keep thinking about other meaningful dates to tie it to.

And finally, once you’re clear on your meaningful milestone date and the goal you’re going to achieve, set yourself some specific mini-goals to make sure you’re staying on-track as the days and weeks pass.

Eighteen months before her 40th birthday, one of my author friends set the goal to self-publish forty short stories and novellas by that milestone birthday. That’s a giant goal and one that called for forty mini-goals. The way she celebrated every one of her successes was a small bottle of champagne. The name of each work-in-progress was written on a sticker then affixed to a bottle and kept in her fridge. When she hit Publish the cork was waiting to be popped.

Back to the months before I turned 50 with that edited manuscript in my hands. I could have decided to start querying agents again with a goal of finding a traditional publisher before I left my forties. But that felt less meaningful to me than hitting publish during the decade that I decided I’d become an author. So, I adjusted my goal, added the word ‘indie’ to published, and have never looked back.

So, over to you! What writing goal has been evading you and what special date can you tie it to, to make a fresh start? And if it’s a big, hairy goal, what mini-goals, or mini-milestones can you celebrate to keep reminding yourself that you are going to be one of the success stories, someone who doesn’t just talk about being an author but is one?

Donna Barker

Donna Barker

Donna Barker is the author of the dark humour novel, ‘Mother Teresa’s Advice for Jilted Lovers’, a co-founder of the Creative Academy, an online community where writers find support on every step along their path to publication, and an embarrassment on the dance floor to all middle-aged, former punk rockers.