The Truth About Those Big Milestone Moments in Writing

From the Tin Man himself.

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I thought it’d feel different.

I don’t know how many times those words have gone through my head over the last few years.

I thought it’d feel different.

… when I reached that subscriber milestone.

… when I made that much money.

… when my post got that many likes (lol).

I thought it’d feel different.

Here’s the truth about being a writer (and a solopreneur, to boot): your life can become a never-ending pursuit of milestone moments, and very few of them provide the “hit” you expect to receive when they come along.

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For example, here are a few milestones I’ve reached in recent weeks:

• Crossed 10,000 email subscribers for the first time ever

• Ran my first week-long email sales sequence (which generated over £1,000 in extra revenue)

• Had my first ever month where 100% of my expenses were covered by writing alone

These might seem like relatively small milestones to some of you, but they were a big deal to me, especially since most of them arrived much earlier than expected.

They were a big deal. But do you know what I felt when they came along?

Not much.

Don’t get me wrong, I’m incredibly grateful to have hit those marks. I don’t take any positive moment in my solopreneurial/writing journey for granted. Not for a second.

But, while I’m quietly excited about the future, none of those feelings make their way to the surface very often.

Maybe I’m just not that kind of person. When my first book was published and family members were gushing all over me like I’d just returned from doing somersaults on the Moon, I was:

1. Quietly pleased and excited

2. Mostly emotionless

Perhaps it’s because I’ve learned to draw a distinct line between personal and business-related matters in my life. There was definitely a time when I did get visibly excited and allowed myself to get caught up in the moment, but that was then. This is now. 2024 David has learned to wait and see.

Wait, because subscriber growth can slow down, or even go backwards.

Wait, because one good month financially doesn’t mean the following six won’t be difficult.

Wait, because life has a tendency to throw big ol’ spanners in the works, just for giggles.

The truth is, you’ll expect to feel a particular way when those big moments finally arrive, and you probably won’t.

Your brain will process the last final step over the finish line as just that: another small step in a long series of them. You can try to manufacture those emotions at the time, but what’s the point? That’s a social media-style response, and it’s tiresome.

Here’s what I think you should do instead.

Have you ever seen the episode of The Office where Jim reveals that he treats himself to a mini bottle of champagne each year after one huge client sale brings in 25% of his overall commission (spoiler alert: Dwight steals it this time round)?

I think you and I should do something like that. Not get drunk on cheap champagne, though. Unless that’s what you want. You do you.

I think we need to get better at marking milestone moments with more than just another discount sale (guilty) or a quick humblebrag post on social media. We need to etch those suckers into our brains forever.

They only come along once, after all.

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When you hit that subscriber mark or complete that novel draft or cross that financial finish line, switch your computer off, put on your shoes and do something to celebrate.

• Go buy yourself a fancy-ass latte in a nice coffee place and people-watch for an hour with no agenda

• Splurge on the biggest box of popcorn you can get and go see that movie you were looking forward to (that’d be my choice)

• Call your oldest friend and arrange to meet for dinner

• Lace up your hiking boots and head for the hills

• Take your kids to the zoo

• Fall asleep on the beach

• Wrestle your dog

Do something to refresh your body, mind and spirit that you wouldn’t normally permit yourself to do. Take the time and space to enjoy the moment. Don’t let it pass unenjoyed.

You and I have to actively celebrate, because otherwise, those brief moments in our personal histories will disappear into the ether, never to be seen or experienced again.

My long, rambling point is this: you most likely won’t feel anything special when those significant moments as a writer come along, and manufacturing emotions won’t help. You need to go out of your way to mark them. You need to “treat yo self” (hashtag parks and rec 2011).

Don’t let yourself become an emotionless tin man like me.

You’ve done the hard work. Go enjoy your reward.

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