I parted ways with a big client this week… Now, what’s next?

Newsletter #7

It happens. Things in the company had been stuck for awhile, and I wasn’t in an area of the organisation that could help unstick it. As a result, there wasn’t much work for me to do, and it became time to move on. 

This past year has been intense, and that’s made me a little lax on the long term planning side of things. Now that I have a bunch of free time, I’m going to use it to chill out, and make some career decisions.

But before I do any of that, there’s one thing I want to do ASAP, and that’s:

Starting to invest

This is a big one. I’ve been passively reading up on this for awhile now and was planning to take the plunge next year. That timeline has shifted forwards and I’m now looking to start investing ASAP. I’m leaning towards passive investing in funds and ETFs right now, but this could change as I learn more. If anyone has any thoughts, advice or books to share, I’d really appreciate hearing from you! I don’t even know how to set up a trading account, so even basic help would be awesome. 

While I’m doing that, I’ll also need to make a decision on what I do with my work life. Here’s a list of things I’m considering doing: 

  1. Building a small app
    It’d be a lot of fun to build an app for Slack or a WordPress plugin. Or maybe something standalone, but small and simple. I think it’d be incredibly satisfying to build something from start to finish and actually launch it into the world. Even if it’s an utter failure, I’d still learn a tremendous amount. The one thing holding me back from this is knowing that I will probably have to spend a lot of time and effort for what will possibly be a tiny profit, or more likely, a loss. The upside is that learning to build a small app leads to building bigger, and hopefully more profitable, ones in the future.
  2. Growing my agency
    If #1 on my list is starting something new, #2 is all about doubling down. It might be time to start building upon the foundations I’ve built. Right now, I have a handful of clients with whom I have good working relationships, and a small team that’s great at what they do and enjoyable to work with.

    I’m actually confident the team can handle larger clients, but it’ll be a lot of painful hard work to grow the agency, and before committing, I need to be sure I want to head in this direction because half-arsing it would be awful for everyone. 
  3. Getting a full time job
    I’m in a weird place in my career. The last time I was a full time employee was 2015. I’ve grown by leaps and bounds since then, way more than a typical employee would, but I have a hard time explaining all that (and even more so in a job interview) because the growth of a self-employed person is not linear and difficult to articulate. In addition, I’ve gotten used to the freedom that comes from dictating my own hours and getting to decide what to work on, and am hesitant about giving that up. I also worry that the employers of the types of jobs that appeal to me (business designer roles / head of marketing at a >1M ARR B2C startup) might prefer hiring someone with a more traditional background. 

    Having said all that, it would be nice to work in a big brand name company, and have that on my CV. Running my own business remains my end goal, but making a pitstop at a globally recognised company is an easy way to gain credibility. 

The options I listed here are neither exhaustive, nor mutually exclusive. Conversely, I feel like there is an abundance of options and permutations, and I want to be careful and deliberate about how I determine my next step. My work values are: 1. It’s important to me that I’m proud of the work I do, 2. it’s fulfilling and 3. it adds value to people’s lives. But all 3 of the above options have the potential to fulfil those values, so I need more parameters to narrow things down.

In particular, I also need to figure out where I want to be in 2020. Focused on making money? Laying yet more foundations? Trying something new?

Also, how hard do I want to be working? 

I have a lot to think about, and don’t expect the answer to come to me immediately. I’ve always been the stewing sort, and come to a decision slowly; but tend to be very sure of it once I’ve decided. Indecision notwithstanding, I’m actually feeling very positive about what awaits.


While I take the time to ponder these options, I’ve been climbing lots, playing ultimate frisbee, riding my onewheel and catching up with friends. Okay, fine, I’ve been doing a bunch of work too. 

Finally, I’ve been a bit of a hermit this past year and I now have the time and mental bandwidth to change that. So if you’d like to climb, throw, ride or imbibe with me, just let me know! 👋

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