Your first year in business checklist

I recently celebrated marked a year in business as a freelance copywriter. Well, a year since registering my business name, first clients came later. But any excuse for cake. How many of these moments did you tick off in your first year?

Going solo in business is tough to explain to an ‘outsider’. There’s more twists, and adrenalin than a toothless carnie’s teacup ride.

Great, awful, fun, excruciating and cringe worthy… how many of these moments have you had in your first business year?

* Note: results promise to be unscientific, unreliable and have no relationship to answers given.

  • Got business idea. Got excited. Ordered business cards, car magnets, calendars, pens and snow globes. Then changed business name.

    Buy all the URLs because you’ve got so many ideas. (Bonus point for letting all of them lapse a year on because they’re complete shite).

  • Week 1: Set working schedule and dressed in office attire (including shoes) to ensure productive day.
    Week 51: Realise you’re still wearing yesterday’s shirt. Dream up a range of functional unitards for work at homers. With enough of a pattern to hide sneaky snack spills, and a revolutionary fabric emitting no body odour. Register

    Realise you’re still wearing yesterday’s shirt. Dream up range of functional unitards for work at homers. 

  • Have actual sleepless nights thinking about business. Or 3am brainwaves. Or woken up sweating about a missed deadline or phone call that hasn’t happened.
  • Week 3: Joined 438 Facebook groups to promote your business and have a ‘presence’.
    Week 33: In 3 groups, with all notifications turned off.

Regularly consider living in an isolated cabin in a rainforest just to get some work done. (Must have excellent Wi-Fi and parcel delivery.)

  • Have done actual happy dance and/or fist pump when closing a sale (hopefully just over the phone).
  • Have hidden from family in toilet for 10 minutes’ peace to answer emails. More than once. Alright… every day.
  • The only time you truly relax is Friday afternoon at about 4.55pm. The emails and calls stop (mostly), and your Friday deadline just became Monday morning.

You’ve dug in a wheelie bin for the receipt for a $1.79 pack of pens.

  • Your control freak tendencies mean your parent/sister/partner is drafted in as your proofreader/book keeper/social media manager.
    They’re qualified, they’re available and the price is right.
  • You’ve considered hurting the next person who says, “it must be great to relax at home all day”. Consider potential jail time would be a great chance to finish your business plan.
  • Referred to yourself as ‘we’ and ‘the team’ more than once. Consider dog and/or baby part of team to justify self-aggrandisement.
  • You’re on a first name basis with the parcel delivery guy and make attempts at conversation. Feel need to explain and justify every parcel. Feel judged. I’m not addicted to online shopping, you are.

You yearn for a break and a chance to relax. Five minutes in, you get a great idea and yearn to be back at your desk.

  • You can spend days at a time running on the smug self-satisfaction of being your own boss – then hit SEEK at midnight.
  • You had a realisation about 9 months in… working from home means you’re always at work.
  • You’ve started talking to inanimate objects at home. Thanking the coffee machine, apologising to the toaster and banter with the fridge are part of your day.

You’re working harder than ever despite this amazing ‘work life balance’ you started your own business for. Feel cheated. Feel elated. Feel all the feels.

  • Sometimes you talk to the checkout person a little more than is socially acceptable. They may know more about you than your partner at this point.
  • Have genuinely wondered if you can change your phone number, delete your website and disappear into the night (where a ‘real’ job awaits).
  • You’ve checked your bank balance every morning to see if anyone paid an invoice. Got smart and set up text notification. Paranoid it won’t work, so still check.

Downloaded 17 time saving for business apps. Never use them, never delete them.

  • Once dreamt of hiring family and friends to build a cosy, nurturing empire. Now could think of nothing worse than hiring family and friends.

Imposter syndrome visits so regularly you’ve given it a set of spare keys. And it knows where to find the spare doona.

  • Taken a business call with a toddler banging on your office door, which you’ve passed off as construction noise. Me either.
  • Your friends are sick of hearing about pitches and clients and wins and how tough solo business life can be. Suck it up friends, that’s your job (shout out to supportive friends, family and colleagues!)
  • Have amazing weeks, days or even a simple moment, when you know you wouldn’t have it any way. It’s the solo life for thee!


How many did you tick off in your first year? Who cares!

Everyone has their own experience. If you’ve made it in small or solo business for a week, a month or a year, you deserve a pat on the back and a tip of the hat. Think of us like the Amish… we live a life not everyone can understand, but secretly want to experience. Raise a glass (and a barn if you will) to yourself. Wherever you are on the journey, you’re a business champion.

Over to you

What’s a milestone moment from your first year of business?

This article originally appeared on Flying Solo, a website brimming with small business advice. Read my articles here.