Like me on a Saturday, plans don’t always work out

2017 was a year of grand plans.

Well, it was a year of one grand plan. One well-thought out, clearly articulated plan and a series of random, haphazardly conceived ideas which I piled atop my grand plan, almost burying it completely.

Lucky for me, 2017 was also the year I acknowledged by tendency to default on my well-intentioned plans, and asked for help.

I started the year with $30K in debt.

It was largely consumer debt, which I find embarrassing but there you have it.

It was having to borrow money from my little brother to cover my expenses that put me over the edge. It was time to sort out my priorities and figure out how to get 'er done, as they say. 

Enter Jim.

My partner, Jim, has a background in finance and is well-versed in Carolyn. He's seen it all go down: the planning, the deviation from the plan and the utter shock when it doesn't all magically work out.

Jim was the ideal person to help me stay the course.

Together, we came up with a plan and some strategies to help manage those moments where I tend to push the plan aside and just do whatever the eff I want.

I thought it might be fun to have a look back at some of those priorities I wrote about, and see how I did (spoiler: not great): 

"I'll be focused on quality time with Jim, more time with friends and family, eating well, writing regularly, and spreading the word about my business."

Nope, didn't happen. When push came to shove this was the first thing to go.

The thing I needed to figure out to make this a reality was managing my time. Sure, I came up with a schedule for myself but I didn't create the habits to support it. I still did a poor job of estimating how long things will take so I took on more than I had time for, which made my pretty little schedule obsolete.  

“If I want to pay off my debt in 5 years and continue to only work part-time at my day job, I'll have to net $350 a month in t-shirt sales (that's net profit after cost of goods sold and expenses) and stick to a budget of $10 a week for incidentals like clothes, eating out, coffee, movies.”

I did exceptionally well here for the first few months, then a little less well as the year progressed.

As far as t-shirt sales, we kept having the same conversation. I’d tell him about a new marketing approach I’d read about, he’d say, “Great. How are you going to apply it,” and I’d say, “I don’t know yet.”

Over and over again.

I never did come up with a concrete plan to actually sell more shirts, so I didn’t hit my targets. Funny that.

“Jim and I are going to meet weekly to have a look at how I'm doing, anticipate any upcoming expenses and determine whether they're in line with my goals. a.k.a. reality check.”

We kept up these meetings for the entire year and they were invaluable.

We had to get really clear, though, about how we would negotiate these conversations, so as to not destroy our marriage.

We decided to start calling Jim my Chief Financial Officer (he sent me an “official” email contract and everything) so that at any given moment, Jim could ask “which Jim are you looking for right now.”

Jim the husband was a supportive listener.

Jim the CFO was a hard-ass.

“Whenever I under-estimate how much time it will take me to do something, I put $1 for every minute I was off into a jar.”

I’ll tell you what, I didn’t stick with this for long (I essentially triple booked myself in January) but boy was it a wake up call to see the loonies pile up in that jar.

I think this is one of those habits that will take a bit of time to undo. My current strategy is to catch myself trying to estimate how long something will take, then double whatever time I came up with.

I had a friend once who was tone deaf. To stay in tune, whichever note he heard he had to sing it a third higher.

It’s kind of like that.

Overall, I’d say I did alright.

I may not have stuck with my plan, but I think that’s part of the process. Learning what doesn’t work and why gets you that much closer to knowing what does.

How about you, did you make any plans last year? How did they work out? I’d love to hear about it in the comments.