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  • Writer's pictureDaniel Phillips

My biggest learnings after 12 months of self-employment.

According to LinkedIn, today marks the anniversary of starting Aftermath, making it officially one year of being self-employed. 

At times like this, I don’t mind doing a bit of reflection, so I thought I’d share a few of my key learnings from my first year as a one-man-band. 

But first, some context.

Pre-Aftermath I was a part-owner and Head of Strategy at Young & Shand. After 7 years there and achieving much more than I thought we ever would have, I felt like I’d done my dash.

Truth be told, I’d probably left it a bit too long to finish up… With the ups and downs of co-running an agency, I was tired, negative and on the verge of being destructive. With a death in my immediate family, I decided it was time to make a break and re-learn who I was and what was important to me.

A key driver of this for me was the insight that my kids didn’t really know me. I realised that I’d spent almost no time with my then 3-year-old daughter in her entire life. It was awful to consider that I’d put so much energy into work that I’d effectively ignored my kids.

So, I left YS and took a few months off, including having an amazing 4 week trip to China with my family. This time did a great job in reconnecting me and those who mean the most to me.

However, after leaving the comfort and relative safety of YS, I found myself needing a sense of job security pretty quickly. Despite having been a part-owner in a pretty successful digital agency I was absolutely petrified to go out on my own… At 40 years old, I’d had a salary for 23 years. Making that change was scary as shit.

With this fear driving me, I started in another business partnership, but that didn’t work out. I had a number of job interviews and offers, but I couldn’t bring myself to going back in to agency land so soon after escaping. The thought of getting a big job and being answerable to a whole bunch of new bosses and not having any skin in the game just didn’t make sense to me.

So I was left with one solution - go out on my own. But I was still really, really scared.

I checked the idea with my wife, my mates, my siblings, my in-laws, my mentors - anyone who would listen to me. I even checked in with trusted past clients and recruiters to see if I had any reputation issues that I might get blindsided with.

In general, people said I was on the right path. I didn’t necessarily believe them but it gave me the inkling of confidence I needed to make the first step.

The most important thing for me was making sure my wife was prepared to go on the journey with me. It was going to take hard work, stress, and money to make it work.. without her support it never would have happened

But it did, and here I am now. A year in. Here are my keys learnings:

Say yes to everything.

This was Duncan Shand's first bit of advice to me when I told him I was going out on my own.

When I started Aftermath I had a fair idea of what I wanted to do. My core offering is a Virtual Head of Digital - I thought that as an offer, with my experience it made sense.

However, I promised myself I would try really hard to say yes to opportunities that came my way assuming I could add value in some respect. On reflection, this has been where the most fun has been had.

In addition to doing lots of interesting digital marketing stuff, with ‘yes' as my answer (to things I may have said no to previously) in the last year I’ve: 

- Co-founded a beer business (

- Co-made a TV led ad campaign which has done a really good job

- Got Australian based and internationally focussed clients (

- Managed to give back by being on a couple of charity boards, doing some mentoring and awards judging

- Had no choice but to go back to being deep into the doing. I’m a much better technical marketer now than when I was in the agency.

There are of course downsides to saying yes to everything. Like being overly busy at times and saying yes to the wrong things, but in general, I reckon its a good way to learn a lot about what you actually love doing. 

I can honestly say I wake up every morning with at least some excitement about the work I'm going to do.

It costs quite a bit of money to go at it alone.

My wife and I have 3 kids under 10 and she has just started back at work part-time after being a full-time mum.  With an Auckland-level mortgage, going it alone at my stage of life is a pretty expensive exercise. Despite having a pretty reasonable first year, it takes time to replace a salary. With set up costs, getting established and all the other bits I estimate my business probably owes me about $70K at this stage. We’d planned for this and feel confident I’ll make that back, but it still hurts when looking at my savings. :(

The stress doesn’t go away, it’s just different. 

I love that I am answerable just to myself and this makes my day to day life much less stressful than when I was at a big agency. However, along with self-employment comes new stresses. Business and cashflow stuff aside, the biggest stresses I’ve felt are;

- After running large teams at YS and realising I didn’t love it, I promised myself I wouldn’t have any employees in the foreseeable future. However, I sell agency services so I have to use contractors to do the work. My team of contractors are great, but they’re not my employees and therefore I can’t expect them to be dedicated to my work all of the time. 

- When problems occur I am the only one who can solve and manage them. I enjoy problem-solving, but having an ally to go into challenging meetings & environments with is missed.

- Sometimes I have too much work on at once. Other times I don’t have enough work. Both situations can be stressful. With no salary as a back up learning to manage that stress is new to me.

- I’m unsure how I will get to take a holiday. I’m in the service business where my clients all take holidays at different times. I'm also involved in a number of businesses which means switching off doesn’t really happen. Burning-out is a risk I will need to keep on top of. 

Momentum drives everything

This is something I learned when working for a fast-growing startup. Without momentum, things die. Ideas, business opportunities, relationships all suffer if you’re not moving forward.

Every day I do a mental (if not actual) check-in on my clients, prospects, and jobs and do at least one thing to progress them.  From the colleagues I’ve seen who’ve struggled in self-employment, this has been the key element that was missing.

Embrace and do the new, but get good advice around you

Being a solo business owner, you have no choice but to do a bit of everything when it comes to running your business. I think it’s important to know where your time is best spent.

For me, I’ve had to learn Xero, but I’ve got a great bookkeeper who does my day-to-day.

Creatively and technically I’ve got a great team around me, but I still do pretty much all concepting and strategy myself as this is what I am most passionate about. My team includes people who I really trust to do a great job at design/art, development, technical marketing, content creation and media buying. Sometimes when I do those parts myself, the outcome isn’t amazing and can end up costing more money than it saves. I’m learning my lessons there. :)

New Zealand is an amazing place to go at it alone.

I have had only support from people around me to do this solo mission. Not only from friends and family but from people who want to help me succeed. NZ is full of good buggers who genuinely want those around them to do well. Being one of those good buggers myself is important.

While just a year in, I feel my journey of self-employment so far has been a very blessed one. I’m thankful to everyone who’s supported me so far: colleagues, friends, family, and clients.

I work mainly from home now. While I may not always be mentally available, being physically around means I’m a lot more connected with my family which was the whole point of doing this. I’m still not very good at work/life balance though, and there’s definitely a few things I need to work on, but I’m proud to say things feel like they’re going in the right direction.


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