Millennial: Pretend Adulting, Real Talk

The Exciting but Miserable Life of Freelancing

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  • 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!)

      • Learn more about your ad choices. Visit megaphone.fm/adchoices

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      Millennial: Pretend Adulting, Real TalkBy Andrew Sims, Laura Tee, Pamela Gocobachi
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