I have a job doing something I enjoy. I get to ask interesting people questions about their life under the pretext of writing an article on them. I get to share these stories with an audience of 15,000+ people, and the feedback I deal with is overwhelmingly positive. Despite this, I’m leaving my job.

Why I’m leaving Timely; Bosses are lame

By the time I joined Timely, I had had lots of odd jobs. I had sailed a three-masted tall ship on the East Coast of America. I had worked as an electrician’s apprentice. I had made websites. I had worked in a kitchen. I had helped renovate houses. I had started a magazine after seeing an entrepreneur on Seven Sharp and deciding to interview her.

I wasn’t qualified in anything particular, although I had half a Diploma in Business. But I enjoyed writing and had done social media work before, so I applied to be Timely’s community manager.

At the interview, there weren’t any Google-esque trick questions or riddles to solve, but Ryan seemed to know my work. Everyone in Dunedin held him in high regard and said that he was a good person to learn from. I was anticipating being able to work with him.

A few days later, he responded with a job offer and asked when I’d like to start. I looked at my calendar. It was Thursday.

“How about Monday?” I said.


Three days later, I joined Timely on my 20th birthday.

One of the first ways I realised Timely was different from everywhere else was when, during the onboarding session, I was given access to most of the company’s data. How much money it was making, how many customers it had, how many customers it was losing (which was a ridiculously low rate) – they had nothing to hide. It was this data that was motivating everyone.

I also realised things were different when I told Ryan that I hated having bosses, and he agreed. Bosses are lame.

At Timely, you’re not judged on your performance. You’re judged on your results. If you work better from 5 AM to 2 PM, and you can prove that’s what gets best results, you’ll have the company’s full support. If you have an idea for a project, you can present it, get feedback from the team, and in most cases, lead it and run with it. Everyone is the boss of their responsibilities.

The other attractive aspect of working here is the flexibility you have, which Timely has dedicated a hashtag and Twitter account to.

“What a beautiful day!” Ryan writes in Slack. “Who’s flexing some #timelylife today to enjoy it and pick up the work later?”

Issy, head of the Onboarding team, is going to the beach. Ryan is taking his son to the park and doing board papers later tonight when his kids are sleeping. I’m having a coffee with Design Dave, talking about basketball and Lion King, and writing this blog post. But when the time comes to go hard, we’ll mobilise and knock out some major projects with half the number of people it would usually take.

Timely’s commitment to helping people succeed is another reason I love this company. When I joined, speaking was my biggest fear. It was never a problem at Timely when I stuttered through meetings I was leading, or through the biweekly marketing hangouts when everyone had to wait for me to finish. There was never a hint of annoyance or impatience other than my own at myself. Timely then allowed me to use my professional development budget to go to a speech therapy course, which culminated in me giving a speech in Wellington’s Cuba Street.

That’s not to say I haven’t struggled with things at Timely. For example, as someone who would be described as both hard-headed and opinionated, Timely’s feedback loop took a long time to get used to. We have a policy where work is shared publicly within the team for feedback. While that means I get to comment on Ryan or Alan’s work, it also means that anyone with an opinion can comment on mine.

After spending a half day writing an article, getting told that my work should be changed makes me want to react. But it’s good to learn how to receive feedback. Even if you’re the best at what you do, there’s always room to grow. While I don’t have to take any feedback I’m given, I am aware that when I do, my work is usually better.

I’m taking the lessons and skills I’ve learned at Timely to my next venture: law school at Victoria University. It’s something I’ve always wanted to do, and to do it to the best of my ability, moving on from Timely is necessary.

Although I’m saddened to leave the friends I’ve made and the audience I’ve worked with behind (P.S. You guys on Facebook and Twitter are the best!), I can’t help but feel glad that I had this opportunity.

Cheers to an eventful year, Timely! I look forward to following your progress as you forge your way in this market and make life easier for the world’s many stressed business owners.

Although I may not be writing your tweets anymore, I’ll definitely be retweeting them.