Updated on 07.20.09

The Simple Dollar Podcast #9: The Realities of Freelancing

Trent Hamm

The ninth episode focuses on the realities and challenges of freelancing, a topic requested by podcast listeners and Simple Dollar readers. Total length: 15:20

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Though I hope you do subscribe using one of the above methods, don’t worry – each episode will be featured in its own post, much like this one, on Tuesday afternoons. The podcast itself may appear earlier than that, however, if you subscribe using one of the above forms, but the notes won’t appear until I post about it here on The Simple Dollar.

Episode Notes
Here are some additional notes that go alongside the comments in the podcast. Approximate times for the corresponding links and notes are listed.

0:00 – The theme song is a snippet of a Camper van Beethoven concert on October 25, 1986, shared via their very open taping policy. Listen to the concert in its entirety.
0:25 – Several of the requests came after my appearance on the July 6 episode of The Personal Finance Hour, where these topics were touched on but not delved into.
1:13 – My primary libraries for such use are Ames Public Library and Parks Library, both in Ames, Iowa.
5:17 – 365 Ways to Live Cheap is basically a small compendium of frugality tips sold at a very low price.
7:45 – Thus, my true hourly wage is higher even though I’m not working more and I’m earning a bit less.
11:22 – Deliberate practice is a big key to getting better at anything.
14:45 – A little preview of next week.

One thing I’d like to do in a future episode is have an audio reader’s mailbag. If you have a microphone on your computer and can record an MP3 of a simple, short question you might have on personal finance, careers, pop culture, or anything else you’d like me to answer, record it as an MP3 and send it to me. Keep the total recording under 15 seconds, please. Also, if you use Skype, feel free to ask your question that way – my username is trenttsd.

Comments and suggestions welcome.

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  1. Moneymonk says:

    The main thing that keeps me from quitting my job is not the income, it’s medical insurance.

    Are you on your spouse insurance? How do you manage?

  2. Jessica says:

    I just wanted to let you know how much I enjoy your podcasts. I was just telling my husband that it is obvious why people like yourself are so successful. I love that you have a voracious hunger for knowledge and are willing to help others find a similar path through providing resources. Really a great podcast. I wish each one was longer. You should start a call in segment like Dave Ramsey. It seems like there are just so many people out there that don’t seem to get it.

  3. Mitchell says:

    I have often wondered what the day to day routine and expences were for a full time writer, this has been thought provoking to say the least. Also, I got to say that you are really coming into your own on the podcast bit, keep it up.

  4. Julia says:

    Trent, I found this fascinating. I’ve listened to a few of your podcasts since finding your website and this one was by far my favorite.

  5. Trent, you can hear the passion in your voice when you talk about what it is you do and how you do it. This is very encouraging.

    More from working at home than freelancing I find that you have less stress and less expense (you covered this) accross the board. As you said, there’s no commute and no lunches with coworkers to pay for.

    But there’s also less stress from intangible factors, like pressure to deal with the artificial stresses of a office environment (meetings, departments with different needs, bureauacracy, covering for coworkers, etc) or trying to keep up and compete with yet another social orbit. Most of that has little to do with generating end product, it’s mostly people control.

    Even if a person can’t freelance in the pure sense, it would be well worth the effort to establish a work at home ability in what ever you do. It isn’t for everybody, but I think it could be for most.

  6. Sam says:

    Great episode, Trent. I really enjoyed it.
    FWIW: I’m in love with that signoff line!

  7. KJ says:

    I believe that you stated that your income is roughly equivalent to that received in your full-time job if you add everything together.

    I’d like to know how you are defining income, as comparing freelancer income to full-time worker income can be an apples & oranges proposition.

    Specifically- $20,000 of freelancer income is NOT equivalent to $20,000 pay (take-home or gross) from traditional employment.

    To do that comparison fairly (to normalize the variables so as to reflect actual available/disposable income) , you’d have to subtract the freelancer’s actual paid cost of individual benefits (such as life insurance, liability insurance premiums, etc.) which would normally be provided gratis by an employer, and also subtract self-employment taxes (paid quarterly), etc.

    Is that how you’re basing your comparison, or….?

  8. Trent Hamm Trent says:

    I’m basing my comparison on my gross compensation from my previous employment, which included health insurance and other benefits.

    I’m on my wife’s insurance, but that was true before I left my job. Her insurance was far better than mine. So, in terms of our family’s insurance situation, nothing changed when I stepped down.

  9. Trent Hamm Trent says:

    I also agree that the podcasts are getting better. Practice is a BIG part of that. I was much more nervous and stilted with the first few podcasts – now, I’m much more comfortable doing it (and I’ve learned how to edit a bit more as well).

  10. Danny says:


    Thanks so much for sharing your financial advice with all of us. I really enjoy your articles and your podcasts are great! I had a small question/comment regarding your freelancing podcast:

    I can’t stop thinking about the part where you mentioned you dress up in the morning for work.

    I actually read about something related to this not long ago, I just can’t remember where. Anyway, the article talked about dressing up (tie and all) for a phone interview. This way, although not physically there with the interviewer, one’s attitude toward the whole thing might become more serious and focused.

    Do you find any truth to this in your experience? In other words, do you feel “at work” when your dressed “for work”?

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