My Ideal Working Situation
working with him isn't so bad (good thing I'm a morning person!)

working with him isn’t so bad (good thing I’m a morning person!)

I’ve been thinking about this a lot.

See, I have a day job I like quite a bit, and I’m not anxious to move on in a traditional way. The work is fun, the position is flexible, and it pays the bills. Also I really like the people I work with and I have a high level of autonomy.

That is to say, I have no reason to complain.

However, I do have a big entrepreneurial streak. I have always been a schemer. I dream up all kinds of scenarios where I do my own thing, I strike out and make money working for myself. I think I wrote once, when asked to describe myself (maybe on a dating website?) that I had an entrepreneur’s mind and an employee’s risk tolerance.

Since the day job is so flexible, I’ve been working fewer hours and supplementing my income by writing. I’ve been writing here, as you know, and I’ve been ramping up my freelance writing at Babble, The Cent, and a few other companies. I’ve also been working on expanding my reach, so I’m writing 1-2 posts per week on other blogger’s sites. Anyone want a guest post by yours truly?

My normal weekday looks like this:

  • 4:45: Wake up. Take Stanley out. Make tea. Start writing.
  • 5:15: Whisper-yell to Stanley about how it’s really not appropriate to wake up the house just because he’s bored.
  • 6:00: Say good morning to Caitlin.
  • 7:00: Run with Brent.
  • 7:45: Finish whatever piece I was working on before I went on a run.
  • 9:00: Shower and head to work.
  • 10:00 – 5:00: Work at my day job.
  • Evenings include family dinners, watching Jeopardy and Breaking Bad and heading to bed relatively early since 4:45 is pretty dang early by anyone’s standards.

I like it, because I front-load my day with work and I get to spend evenings with the people I care about instead of in front of a computer screen. I’m a morning person (don’t punch me!) so my brain pretty much shuts down after about 8pm anyway. This schedule has worked for me for the last two months. Before that, I was getting to work around 8am and was stressed because I couldn’t find time in the day to fit everything in.

Now that I’m looking ahead to 2014, I’m trying to figure out what my ideal day looks like. And even though I am a morning person, I’m not sure I’d set my alarm for 4:45 if everything shifted!

This is what I think my ideal work day looks like:

  • Puppy O’clock: wake, take Stanley out, make tea. Go to the office (because in ideal land, the spare bedroom will function like an office) and turn on the computer. Write.
  • 7:00: Run with Brent.
  • After the run: back to work writing. Focus on building my own brand at least as much as freelancing.
  • Later in the morning: yoga, then a shower.
  • Mid-day: walk the pup, go into the office for a bit (four hours?).
  • Late afternoon: work on the other project. I’m going to start a caramel business in 2014 and I’ll need to dedicate time and energy into that. Afternoon energy is great for creating.
  • Evenings as usual.

Looking back on this, my situation right now is pretty close to ideal. Puppy O’clock is like 5, 5:30, so we’re not talking about a luxurious sleep in. I’m not doing much about the candy business other than scheming but having an outline of how the day will go makes it a lot less daunting.

I can do that, I really can.

I’ve been thinking about trying to make caramels for years. Ever since I first started making them for friends and family around the holidays, I’d think, “I wonder if I could ever make money on this venture,” and I’d think about it… heck, I’d play around with logos and websites for an entire weekend just because dreaming about it gave me such joy.

But then I’d get back to work. After all, the credit card debt wasn’t going to pay itself, now, was it?

So now we’re here, and I have a savings cushion, and I’m going to make a go of it.

Wish me luck!


  1. says

    Kathleen, did sounds like such an amazing way to spend your day! I'd love to live a similar life one day, hopefully sooner than later!

    By the way, You puppy is just adorable :)

  2. fitnpoor says

    Puppy o'clock! Hilarious! We have puppy time every moment of the day. She manages to figure out how to weasel her way in to our days as much as possible.

  3. says

    I think it's great that you have flexibility to do the entrepreneur thing while still having your day job. Freelancing is as far as I'm willing to go because I just love the steady paycheck and amazing benefits.

  4. says

    Woo! Keep us us posted.

    I am a night person but I prefer to work an earlier shift or a 9-5 so I have my evenings to myself. Working a late shift really took it out of me.

  5. Anne - Unique Gifter says

    Yay!! I can't believe you wake up so early! Those sound like mighty fine days to me :-) I'm excited to hear about the caramel business going live!

  6. deardebt says

    You wake up early! I am a night person and stay up till midnight every night or later. I do feel kinda zapped about blogging at night, but I've tried the morning thing and it doesn't work for me. I think you have an awesome schedule and I'm so happy your work is flexible. I'm sure you will be a success with the caramels. I am always here to taste test :)

  7. The Wealth Gospel says

    I would love to be able to get up earlier, but sadly my wife is a super light sleeper and if I wake up at 4:30, she wakes up and can't go back to sleep. Then I get to feel her wrath the rest of the day :) But we'll figure something out someday! And good luck on the caramel business! It sounds delicious

  8. Budget & the Beach says

    Man 4:45 is early. I was trying to wake up at 5:30 but I still found that too hard. I think 6:30 is my idea time. Anyway, good luck with the business!

    • says

      I just love the mornings, and I know myself well enough that I can't try to add productive things in the evening. It never works! So if I need more hours, I take them as soon as I'm up. :)

  9. lisavstheloans says

    4:45?!?! Oh man – I've been struggling to get up at 6! Once I get into the swing of it though, then I think it's totally do-able. It's just that first day!

  10. says

    Mine is pretty simple. A job that I could earn more than enough and have my lifestyle untouched by it because it sucks to make some huge sacrifices for your job because you end up regretting and having resentment.

  11. impersonalfinanceroboto says

    Awesome- sounds like you have it planned out! I'm still trying to wake up as early as you do, because I love having my nights free as well. Best of luck in 2014!


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