Episode #10×19: The Exciting but Miserable Life of Freelancing

  • Welcome to #Millennial, the home of pretend adulting and real freelance talk!
  • First things first! We’re pouring one out for Laura Tee, who couldn’t make this week’s show due to COVID.
  • In Laura’s absence, Andrew and Pam open up about life as full time freelancers. 
  • Our discussion this week is inspired by a few questions we got about what it’s like working in freelance full-time. We hope this chat helps anyone else out there looking to make the switch to self-employment!
  • We kick things off on a positive note and detail the upsides of freelancing. The perks include flexible schedules, working from home (or from anywhere you want/can!), and following your passions.
  • Are Pam and Andrew really happy working freelance full-time?
  • How do we combat the fear of knowing our jobs aren’t guaranteed in the same way that working a traditional corporate job is?
  • Have we ever had to chase down clients who just don’t pay us on time?
  • Elsewhere, the topic of 401Ks and healthcare comes up when we dig into the downsides of life as freelancers.
  • How do we go about securing health care? How about saving for retirement?
  • Ultimately, would Pam and Andrew recommend going freelance to others in the year 2024?
  • To wrap things up, we take a few questions from listeners:
  • What do we wish we knew at the beginning of our careers?
  • How do we show people we’re capable of doing the job they want?
  • How do we battle imposter syndrome?
  • Do we stress out about not having a consistent paycheck?
  • This week’s recommendations include: Wave Invoicing (Andrew) for an easy-to-use system to draw up professional invoices, and Whole Foods’ coffee bar (Pam) in lieu of chains for more affordable coffee.

And in this week’s installment of After Dark, available on Patreon and Apple Podcasts:

  • Our Friend Series continues, and this week we’re tackling the tough topic of lending friends money.
  • To kick things off, Andrew shares a personal story in relation to this week’s AD theme
  • Have we ever had friends ask to borrow large sums of money? And what do we do when they don’t pay it back?
  • What about when it comes to lower stakes instances like spotting a friend for coffee or lunch
  • How late is too late to ask your buddy to Venmo you back for that dinner you put on your card? Asking for a friend (no really– we are!)

Download now