Progress Report: I’ve Bought Myself a Day!

Hear ye, hear ye!

It is with great pleasure that I would like to announce I’ve officially taken the first step on the road to ultimate freelance freedom:  I’ve requested one day off work each week to focus more on my writing—and my boss agreed to it!

This is a step I’ve been contemplating for a while now, but I had to make sure enough stars were aligned, enough i’s dotted and t’s crossed, to make it a smart, productive step rather than a holy-crap-I’m-leaping-something-please-catch-me step.

For you kids following along at home with this whole grand master plan of mine, here’s a rundown of what led to this decision, what I’ve learned from it, and where it’s leading me to next.


How I Got Here

I started off at my firm 10 years ago (I know—good lord!) as a part-time clerk my freshman year of college.  I answered phones.  I filed things.  I got people coffee.  I cleaned up the spills in the kitchen from other people’s coffee.

I was a lackey.  But I was the best damn lackey I could be.  And I always wanted to be better.  I studied previous cases, teaching myself the firm’s systems and formats, learning the language we use for our pleadings, picking up whatever I could about the way things worked.  Sometimes I saw ways things could be done more efficiently, so I tried ideas out.  I created a billing system.  I created a library system.  I generally tried to make myself useful.

I could have just asked people what to do every time I ran up against something new, learning only what I needed to know to do the immediate project at hand and sticking with rote performance.  But that’s just not my style.  I’m an overachiever and full of antsy energy, and quite frankly, I get bored with just going through the motions.  And to my surprise, while bringing my A-game simply because B-games annoy me, people started to take notice.  They gave me more responsibility.  They seemed to value my input.  Instead of dictating letters to me, attorneys started giving me instructions like, “See what you can do to draft a response to this.  Here’s the vague idea…”

I became the receptionist full-time when I graduated college, then personal assistant to one of the partners, then a learn-as-I go paralegal.  I still did the coffee-spill-cleaning as needed, because I was still counted on for all the other stuff I did previously.  But I was advancing at the same time.  I got on the letterhead.  I got business cards.  I got my own (well, shared) office instead of the constant-state-of-interruption reception desk I’d outgrown.  And since I’d come up through the ranks, I knew a fair amount about pretty much every aspect of the day-to-day doings at the firm.  I became the go-to girl for everything from printer jams to client crises, and although that frustrated the daylights out of me sometimes, I went-to with all my might.  And it paid off.

I’m still a little dazed that it did, and as well as it did, but you know what?  I’m gonna run like the wind with it.


What I’ve Learned


Lesson #1:  Be a Linchpin (a.k.a.  the Best Damn Whatever-You-Are You Can Be)

If you haven’t already read it, I highly recommend Seth Godin’s Linchpin: Are You Indispensable?  It will make anyone amped to bring their A-game to the office every day.  It’s the inspiration that led me to the philosophy I laid out in “How to Be an Awesome Employee In a Less-Than-Awesome Job.”

Linchpins are the people that stand out in an organization.  They initiate things, they seek to improve things, they create solutions instead of reacting to problems.  They’re proactive, engaged participants, not just seat-warmers putting in the bare minimum for a paycheck.  They make a difference.  They become an integral part of the team.  And people start to notice.

I put in my time over the decade I’ve been with my company.  I worked my pretty little tail off to do the best job I could, at whatever my task was, and because of it I proved myself to be a valuable resource.  When I went in to propose my one-day-a-week-less plan to my boss, he didn’t get P.O.’ed at me and fire me on the spot for being an upstart.  He actually congratulated me on my freelance success and offered me a better proposition than I’d gone in with.  (More on that in a bit.)

Disclaimer so I don’t feel like a total douchebucket:  I didn’t do all this strategically to gain leverage.  I’m not that calculating, or opportunistic, and I sure as hell had no grand master plan back when I was 19.  But, I’m glad it worked out this way, because it truly proves that you can control (and make) your opportunities just by approaching things with the best you can give. Hustle pays off.  (Hustle with a smile pays off even more.)


Lesson #2:  Dreams Need Plans.  That’s Not Horribly Exciting, But It’s Best for the Dreams.

Like I discussed in a recent Brazen Life post, sometimes it’s better to view your “day job” as the funding for your dream rather than a mortal enemy you need to bail from as soon as possible.  Going quitsies in one fell swoop and praying for the best may seem like the most poetic and honorable way to chase your dream—but when you find yourself scrambling for next month’s rent money and the only gigs biting pay $2 for a 1,000 word article, guess what you’re gonna wind up doing?  Not so good for the quality of your dream, or your happiness.

I’ve been ridiculously careful in evaluating whether I was ready to make a change.  I calculated exactly how much pay I’d lose per week if I cut a day at work; I knew how much I normally bring in a month with my freelancing; I had a few month’s worth of gig money saved up to cover any initial slow periods once I made the change.  I knew what I was giving up, what I needed to cover the difference, and I talked everything through with the husband to make sure he was on board with it.  The leap doesn’t feel nearly so gut-wrenching because of this; it just feels like the next natural progression of my journey.

I was a little stunned when my boss actually offered to work with me on a week by week basis, meaning if things are slow with my freelancing, I can come in for a full week whenever and not have to worry about paying the electric bill that month.  (I’m sure his logic ran more along the lines of “I can get an extra day of work from her,” but still, it’s a huge bonus.)  That was a safety net I wasn’t anticipating.  But when I made the decision, I was 100% prepared and willing to take whatever action I had to to keep the budget up after I switched.

Taking a part-time dog-walking job, selling some of my things on Craigslist, making t-shirts on Zazzle to bring in extra revenue—I knew I’d never be in a position where we’d be in serious financial trouble, but I also knew I was going to have to hustle extra hard and probably make some sacrifices, and I was o.k. with that.  I was ready to make it work.


Lesson #3:  Don’t Save the Good China

Part of the reason it took me a while to decide to finally make the change was because I’d been viewing my freelancing income as an untouchable savings fund—something I had to diligently squirrel away until I got such a large, self-supporting balance I could just call it quits once and for all.  I didn’t just want to be careful; I want to be super, extra-special careful.  Using any of it now seemed greedy and impulsive.

But the more I considered it, the more I came to realize something:  the whole point of embarking on freelancing was to give myself my life back.  To let me work on something I love on my own terms rather than being chained to a desk in a career I don’t care about.  And I can start having some of that life now.  I’m already making my dreams on a reality, on a small, gradual scale.  I shouldn’t look at that as an irresponsible premature leap—I should look at it as a flippin’ marvelous little success.

I just bought myself a day a week with my freelancing.  As things progress, I’ll buy myself another day, then another.  In the meantime, I’m granting myself a little extra sanity and a lot more of the things I love, rather than waiting for some grand “some day” payoff when I can finally enjoy all the work I’m putting in now.  There’s no point in saving the good china if you never find an occasion worthy enough to bring it out.  I’ve worked durn hard to get to the point I’m at, and I’m ready to allow myself to enjoy some of the results of that.


What I’ve Got Planned

Oh baby, what don’t I?

There’s an ebook on the CCIQ philosophy—in the final stages of drafting now, with an editor and designer lined up to start bringing this puppy in for a landing.  (Mixed metaphor, I know, but excitement leads to linguistic lapses.  Fie!  Land, puppy!  Land!)

There’s an active e-mail list—a real, honest-to-goodness list for all you poor, neglected souls who signed up for one and haven’t seen a thing from it since. Cross my heart.  You’ve been so patient.  Your Insider status will be giving you all sorts of fun shite in 2012, from extra doses of inspiration to the possibility of seeing me in all my panda-hatted glory in some exclusive Insiders-only video blogs.  For reals.  The more I consider doing them, the more excited I get about it.

There’s a book-book of some nebulous sort—possibly semi-autobiographically about my descent into craziness, possibly the dystopian fantasy I’ve had in my head since I was 12 and keep secretly revisiting like a guilty love affair, possibly some sort of Eat-Pray-Love accounting of what it’s like to call it quits.  Most likely all three, worked on simultaneously, ’cause that’s just how manic me rolls.

There’s more bloggy goodness, and interaction with all you lovelies, and who knows what else, all coming down the pipe.  Why?  Because I can.

That’s right.  Because.  I.  Can.

And pssst…you can too.


What’s YOUR “next step” going to look like?

Image: Jesse Menn / Flickr

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  • I am hoping to follow a similar path, but never thought about the option of moving slowly instead of taking a giant jump. Thank you, thank you, thank you!

    • You’re quite welcome.  If you’re looking for added inspiration while you’re making the gradual change, I’d highly recommend the book “Quitter” by Jon Acuff.  (You can find it on my resources page.)  It lays out a really sensible, persuasive argument for why it’s much better for your dreams to take thing slowly and carefully, rather than leaping all at once (which is what I’d naturally do if no one had told me better.)  🙂

  • Congrats! When I heard this, I thought you were still getting paid on salary but getting an extra day off. Needless to say, I was jealous! Now it makes a bit more sense, and instead I am impressed with your gumption.

    My job is semi-flexible, but it involves writing more than 100 features a year and editing three publications, so I can’t exactly freelance out any more of my writing on a regular basis or ask for a four-day week (even though I do some work at home.) Plus, between the blog and book, I don’t think I have any creativity/research time left for freelance. I’ve done it from time to time, and to be honest, I would be in the poor house if I had to live off that income alone!

    With that said, your plan is great and it sounds like exactly what you’ve been striving for.  You know what you want and are taking the steps to get there. I look forward to seeing you climb up the ranks!

    • Thanks, Abby.  I wouldn’t play down the importance of your blog and book (or of the fact that you’re doing a job that actually lets you write for a living!)  You’re doing pretty darn well for yourself also.  All that matters is that you’re happy with where you are.

      Who knows whether I’ll ever make enough to take off another day, and another, and another (or how quickly that point will come), but for now I’m just happy knowing I’ve been able to take a step.  A day in my PJs doing freelance while watching HGTV in the background?  I’ll take it!  (Even managed to squeeze in a nap last Friday to fight off an oncoming cold.  Huzzah!)

  • Shanna Mann

    High Five!

  • Huge congrats on the day off and upcoming news!! I appreciate you sharing the steps you took along the way because it shows just how much time and effort is needed to make dreams happen. I think we all love to read the success stories about someone who quit their job and then became a fabulous, wealthy CEO of a skyrocketing company, and we like to believe that all happened over night. Ha! I doubt true success ever happens over night and if it does it’s usually in the 15-miutes-of-fame variety (aka all reality tv stars). Lasting success and the true happiness that follows is a bit more calculated and planned out – exactly what you’re doing. Congrats again!

    • Thanks so much, Lindsey!  I’m actually thinking of writing an ebook on how to survive running a side hustle while holding down a full-time (or nearly full-time) job.  So much is out there about how to get the business off the ground, but there’s not much practical advice when it comes to how to survive the day to day craziness of a double life.  I have a feeling it could really be useful to a lot of people–I could certainly use a guide and motivational jump start often! 

  • I applied for a scholarship to the makeup school that I wish to attend in the summer.  Until that time comes, I plan on practicing looks on friends and family, as well as apprentice under local makeup artists, to get my feet wet.

    • Good for you, Ashley!  That’s so awesome that you’re taking steps towards your dream.  It sounds like you’re going about it just the right way, working to get some experience before you take the next step.  Good luck!

  • Yay!!!!!! I’m so happy for you! I did a similar thing a couple of years ago (cut back to 80%, but I took my 20% in mornings), so I know how great it feels! Awesome about the bonus safety net, too. I hope it goes great for you and you love it!

    • Thanks, Cara!  I really appreciate all your support.  It’s been a huge help (and inspiration) to have someone who’s done it to show me it’s possible (and let me know it will be o.k.)  🙂

      Take a look at my response to Lindsey above–would you have any interest in possibly writing a short section on what it’s been like for you?  Just a few paragraphs about the issues you faced, things you wish you’d known, tricks that helped you make it happen.  I’m hoping to include “real life” stories from hustlers who’ve broken through, and you were the first person that came to my mind.

  • Danielle

    Wow, can I ever relate! Every job I’ve been in I was a linchpin. I never knew there was a word for that. The problem I kept encountering was I got bored too easily and outgrew my position (and had to do waaaay more, for the same amount of money). Finally after five years of hustle, I’m in a place that recognizes how hard I work and how much I bring to the organization.

    It’s great when ass busting pays off, and more so when you see others in my age group doing the same. It seems older folks tend to see younger ones as slackers and entitled brats. 

    • Hey, Danielle!

      I’m the same way.  The way I became a “linchpin” myself was largely because I also just get way too bored doing the same things over and over again.  So, I’d explore other tasks I didn’t know how to do yet, learned more about the cases my firm handles, asked questions…and slowly began to take on more and more responsibility.  Now I know about pretty much every aspect of our work, which gives me a value I can leverage to create a more flexible arrangement for myself.

      I’d highly recommend checking out Seth Godin’s “Linchpin” (you can find it on my Resources page under books on “Work”).  It’s where I too recognized there was a term for my style of work–and also a ton of power that comes from approaching a job that way!

  • Congrats!! So many times we read about people who go after their dreams while they are still at home with the parents, or over 45 and debt free … You’re keeping things real and in perspective- I admire that!!

    I’ve been making bows for a while now more of a hobby than anything else and now I’m actually getting some business out of it… I LOVE LOVE LOVE it so much, but hardly have the time to work on it .. BOOO!!! So.. I’ve done something similar to you… well more like taking advantage of the situation: During the summer we have a choice of how we work.. I asked to work 10 hr days with a friday off or 9.5 hr days with half a Friday off- Yup.. guess what I’m doing over the summer =) I also want to learn more about blogging and actually put to use all the stuff I learned in college

    Again.. congrats on your “take- off” !!!

    •  Good for you!  Side hustling isn’t easy, but it can be SO worth it to know that you’re making steps towards doing what you want.  And I think blogging would be a great way to expand yourself (although of course I’m biased toward that medium).  😛  You could use it to channel people to your business, write about what it’s like to start a business, or anything else under the sun.  The people you’ll meet and the things you’ll learn about yourself are worth it in and of themselves.

      Thank you for the kind words, and best of luck with your own endeavors!!