The Digital Monkey Show · Episode 1

Freelancing vs working in a company: which do you choose?

Phuong and Jay kick off the series on the freelancing versus employment question. Having done both, they weigh the freedom against the security, the reality of being your own boss, and whether you should hand roles to your clients.

Approx. 45 min Video podcast Phuong & Jay
The Digital Monkey Show Episode 1 with Phuong and Jay

Watch the full episode. The video opens on YouTube when you press play.

About this episode

The very first episode of the show, back when it was still finding its name. Phuong and Jay take on a question a lot of creatives wrestle with: freelance for yourself, or work for a company? Phuong has done both, so he talks candidly about the freedom and the opportunity of freelancing against the security and structure of a job.

They get into what it really takes to be your own boss, why freelancing is not for everyone, and a spicier debate they flag from the start: whether you should provide roles to your clients. It is a loose, honest opener that sets the tone for the series. This podcast is no longer running, but the conversation still lands. AM Visuals grew out of exactly these kinds of decisions.

Phuong hosting The Digital Monkey Show Episode 1
Phuong hosting The Digital Monkey Show Episode 1
Freelancing is a great opportunity, but you have to ask yourself honestly: do you have what it takes to be your own boss?
Phuong · on going out on your own

What you will take away

  • 01
    Freelancing is real freedom, with a catch. You choose your clients and hours, but the responsibility for everything lands on you. The upside and the risk are both yours.
  • 02
    A job trades freedom for security. Working for a company gives you stability and structure. For some people that is exactly the right base to build skills on.
  • 03
    Being your own boss is a skill. It is not just about talent. Discipline, sales, and managing yourself matter as much as the craft you are selling.
  • 04
    Try both if you can. Phuong has been on both sides, and that experience is what lets him weigh the trade-offs honestly rather than romanticising either one.
  • 05
    Know yourself before you choose. The right answer depends on your temperament and stage of life, not on which path looks better from the outside.
Jay on The Digital Monkey Show Episode 1
Jay on The Digital Monkey Show Episode 1

Your hosts

Phuong Tran
Founder · AM Visuals

Phuong founded AM Visuals and hosts The Digital Monkey Show alongside his brother. He brings the video and business lens, and plenty of hard-won opinions on running a creative company.

Jay Tran
Co-host · The Digital Monkey Show

Jay is Phuong’s brother and co-host. Together they trade honest takes on business, content, and the realities of building something of your own.

Phuong mid-conversation on Episode 1
Phuong mid-conversation on Episode 1
I have been on both ends of the spectrum. There are good things and bad things about each one.
Phuong · on doing both

Questions this episode answers

Full transcript

This transcript is auto generated and lightly edited for readability, so small errors may remain.

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