Midlaning as a Freelancer

The midlaner dictates the pace of a game. You achieve this through mechanical skill, strategic decisions and an adaptive mindset.

It often starts as a role of solitude, but it’s this exact independence that gives you the leverage to set a team’s synergy and tempo. A successful midlaner roams free, has good awareness, and knows if he needs to be a playmaker or a space-maker for his team. “The strength of the pack is the wolf, and the strength of the wolf is the pack.”

Freelancing feels the same way.
It’s no joke though, going from a 9 – 5 to a 24/7. Because suddenly, I’m responsible for e v e r y t h i n g.
On top of that, what made the leap harder was saying goodbye to colleagues I grew to trust deeply over the years.

Skunks, you have been the warmest bunch of professionals I never expected. The last few years have been more than memorable, I can still daydream our lunchtime conversations, meme sessions and Australian jokes. You’ve also contributed to my growth and thinking more than I can be thankful for, which is why the decision was so tough, and why I procrastinated on it for so long.

But when opportunities come knocking and you don’t answer the second… or third time, it feels like the universe comes leaning in to smirk, while asking:

”Well? Do you actually want it or was it all talk?”

I was torn between two choices: the warmth of comfort or the potential for growth. Comfort meant stagnation, while growth meant discomfort.

It’s a paradox I’ve been aware of from working out. But in work, it hits different, especially when it’s a life-altering decision.

But the Timekeeper waits for no one and I knew I had to make a decision. It’s been 9 months since then, and here’s a letter I wrote to myself when I was overwhelmed by the thought.

Since then, I’ve made decisions to pave this path of mine – again. I’ve gotten a lot better at it because my general skills, communication and time management have improved. As foretold lol.

Here’s what moonlighting for my clients have reminded me about the role:

1/ Productise yourself

I picked this one up from Naval Ravikant (How to Get Rich Without Getting Lucky).

When you start working solo, your business isn’t your brand. You are your brand, and your brand is your business. It doesn’t have to stay this way, but it definitely starts here.

With that in mind, you are the main product. Of course the deliverables are important, but it’s your judgement, decisions, communication and reliability that makes it more valuable. It’s also your personality, sense of humour and people skills that enable strong working relationships.

Find ways to show this, not just through marketing, but in your daily habits. This could as simple as replying consistently at the same time each day. It’s one thing to say you’re reliable, it’s another to know you are, even when there aren’t emails to reply or clients to meet. It’s a reassuring feeling to know you can count on yourself.

The best way I’ve learned to do this is by doing the hard thing even when times are hard. It’s a cheat code because when you can do the things when no one is watching, it becomes that easier when it’s expected.

It’s as the saying goes: ”how you do anything is how you do everything.”
There are mixed sources on the origins of this quote, but I heard it first from the Marquis Vincent de Gramont in John Wick 4.

Spoiler alert, he’s not a good role model, but wisdom comes from strange places.

2/ Communicate expectations

With yourself, you’ll have to negotiate some boundaries. These usually come in the form of your working hours, the non-negotiables and the promises you make for yourself. That can mean different things for everyone. For me, it’s waking up at 5am for leg day, and posting these blogs before Tuesday. With clients, you have to educate them on your services, deliver on agreements, and negotiate payments.

Once you’ve gotten verbal confirmation, organise your list and formalise it as an email or PDF along with a quotation/invoice. This will elevate your clients’ status while enhancing professional credibility and clarifying deliverables. While they are holding you to a standard, you’re also holding them to one. It’s a win-win that builds mutual respect.

3/ Set deadlines

This goes hand-in-hand with point 2, but I think it deserves it’s own spot on the list because it’s where I found myself trapped when I was a young creative and ideally, you’ll steer clear of it because it can drain your spirits. Unfortunately, our energy is finite, and the best way to utilise it fully is by running a solid schedule.

When I first started freelancing, I used to leave timelines flexible and “go with the flow” but that’s where energy drains fastest. Use a calendar, schedule ahead, and honour your commitments.

Be kind to yourself – set realistic deadlines. Then, meet them relentlessly. A deadline will protect your time, energy and your clients’ trust in the long run.

4/ Be a damn good mirror

Every time I hop on a call with my clients, the first word I write in my notebook is “listen”. It’s a trick I picked up from an entrepreneur some years ago, I don’t recall his name but it’s been really useful. Almost everything you need to know is in what they share, just remember to prompt them with thoughtful questions and sincerity. I think of it as interviewing a patient in pain. The clearer the problem, the clearer the solution.

We all want to be understood, so acknowledge your clients (nodding works well) and let them see you taking notes. They’ll feel heard and trust you more. Something I’m trying to get better at is reading subtle body language. The body speaks when the mouth does not.

Lastly, be curious. Start with broad questions, then zero in on the details. More than half the work is done just by paying attention to what they have to say.

Funny how the things they don’t teach you in school seem to be the most important things in life.
I’m grateful to have picked these up over the years, and I hope it helps you too.

I’m going to keep it up and see where it takes me. Until next time, see you in the mid lane.