How I Started My Business + The Secret To Success (it's clickbait)

Tuesday, March 28, 2017

Tax man called. He wants his money.

Once upon time, pre Chicago, pre working for myself, I had a job where I actually enjoyed tax season. I got money back! What a thrill that was for me. I went right out and bought a new Kate Spade purse if I remember correctly. Oh to be 23 with no responsibilities or no other mouth to feed!

*Harlow is my only other mouth to feed, but he's got expensive taste and won't eat his dry dog food unless it's covered in an expensive (organic non GMO) meat log he makes me buy for him.

As I've mentioned in a few other posts recently, March is a weird reflection kind-of-month for me. It's a time when I can't help but remember getting fired from a job, and then one year after that (there was a lay-off in there too) I remember filing my taxes and seeing that I owed $500 (for the random 1099 jobs I had that year) and I broke down crying.

I didn't have $500 in my bank account and so I had to pay my taxes that year on my credit card. It was a really low moment for me and I swore to myself I'd never be in that place again. I think it was extra hard for me because just two years previous I was in a pretty good place financially, thanks to that job I snagged right after college (recruiting for a culinary school) and so it felt like a real kick to the gut going backward.

And let the record state (someone's keeping a record of this, right?) that I take full responsibility for being in that position. Yes I was laid off and fired, but after I was laid off in December I refused to take a "real job" in pursuit of getting this blog going. So yes, that led to being very broke for awhile.

I used all of my free time to turn this blog into my job, to be honest though that meant something different four years ago than it means today. This was pre Instagram! Did you know that time even existed? The good news is that I almost get giddy these days thinking about all of the ways a small business owner can grow their business, it's literally at our fingertips.

But a few years ago I didn't know this and my blog barely sustained me. I felt like I was constantly struggling to keep my head above water. I was still putting everything on my credit card at this time (which I pay off in full every month now, don't worry mom.)

However in hindsight, paying $2500 for comedy classes at both Second City and iO probably wasn't the best idea during this point in my life... But you know what? I don't regret those classes either. I bought friends (#gumps!) and I'm pretty sure both of those wacky institutions are what kept me sane and happy at this time in my life.

But now I'm getting sidetracked reminiscing on the years I spent learning how to play make believe on stage with some of the funniest people I've ever met.

As I was saying... about taxes. blah blah blah.

As a small business owner I pay quarterly, but I underestimated a wee bit this year, so I'm having to send in a little more. And last week when I figured out what I owed my initial reaction was oh shit (as usual) but then I couldn't help but feel super grateful, as well. I've felt this way every year since the credit card year. Of course it sucks to owe a lot, but I can tell you from experience it's a helluva lot better than the opposite. It feels good to grow something.

Truthfully, I consider this blog a part time job now. My tshirts are the full time job. But I also know that the tshirts are a full time job thanks 100% to this blog. Thanks to you. I know that the only reason I sold my first 20 shirts was because you came here and saw them.

Man, did someone put some warm fuzzies in my coffee this morning or what? I'm telling you guys, March messes with my head. But in a good way. A grateful way.

Long story short, if there's anything I've learned over the past five tax seasons, it's that there's no "secret to success," there's no "one thing you should do" to find financial gain.

You have to do everything you can. And keep going until it works. That's what I did, anyway. And when it stops working I'll find a new thing and hustle the hell out of that. I've said it before and I'll say it again, I'll do whatever I have to do to keep me out of that cubicle.

And now if you'll excuse me this post has once again struck a little fear into me and I need to get back to work before someone comes along and pulls this rug out from under me.

Tony Robbins


  1. Thank you so much for this post. I was fired from a job in March 2 years ago; so I get it on the March thing. I'm sadly still in cubicle land, but finally started actually posting on my blog a few weeks ago. I'm just getting started, but I finally have that fire to hustle and make it all work for me.

  2. It was great reading about your experience. Really helps so much to reassure me that there are people who started out just like me, making it to success! One day, one day!

    Charmaine Ng | Architecture & Lifestyle Blog

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  4. This post is EVERYTHING!! I started a blog a few years ago, and just kind of let it slip away, but YOU inspired me to get back in it!

  5. Loved this post. It always makes me so happy to see people killing their goals!

    Allie |

  6. No one likes to owe the tax man money happened to Tim and has happened to Kathy, not me I don't have a paid job thus don't pay taxes as don't have money, just saying. Now all that said, loved the post, just so you know

  7. Loved reading this! I've been reading your blog since the Second City days, and it is so inspiring to follow your journey.

  8. All the praise hand emojis! As I sit in my cubicle... Not much longer left in that life though!

  9. I am amazed by those who can take blogging to a whole new level. I've been teaching for 21 years. Even though it is tough sometimes, I really like it, and every day is new with middle school kids! 21 years is a long time for one profession, and admire those who can break the mold and follow a different path. I've always just been plain scared to get away from a check that I know is coming every week and insurance and retirement is always included. Sometimes I wish I had been brave enough to branch out and do something different!

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