Plancrastination: how love of the starting line is keeping you from the finish line

New journal, phone and laptop are required for productivity, right?

As December began I had the undying urge to end 2017 and begin fresh in January. While this desire to “start over” certainly isn’t unique to me, I do find it manifests in some interesting (and dangerous) ways for entrepreneurs.

We can all agree that 2016 was the year that wouldn’t stop taking as our heroes died en masse and an election cycle stretched the bounds of decency and our collective patience here in the US and rippled across the globe. The year was so bad that Australian comedian Adam Hills bestowed the annual title of “Dick of the Year” to 2016 itself during The Last Leg’s annual wrap up show (even as the host learned, on air, that guest and friend Carrie Fisher was in critical condition).

2017 can be summed up in a word for me: resistance.

I confess, it’s not the word I chose in my starry eyed, hopeful planning of the year but from marches and sit ins to sexual assault allegations and special investigations, every day felt like a struggle.

Is it any wonder I can’t wait for January?

In these dark and gloomy days of December, I yearn to flip the calendar to a fresh page, open up a new date book, try a new shampoo — anything to create the sensation of a fresh start.

But in doing so I’ve realized that there’s a pitfall that ensnares far too many entrepreneurs and freelancers and it’s not just consumerism that leaves us wanting a new computer, phone, business cards and office space. It goes deeper to the very definition of success.

We’ve all heard of “Bright Shiny Object Syndrome” but in my book I share that it’s more honestly called “OMG I’m stuck on this thing and no one will help me figure it out so I’m going to go over there and work on something that seems easier now, #okaybye” Syndrome.

Not as pithy, but you get the idea.

Having a tendency to horse trade to a new idea, project or business plan isn’t just time consuming and risky in practice, it smolders all of your momentum and previous successes and effectively puts you back to square one, yet with the sense of accomplishment that comes from “making decisions” without actually “doing the work.”

Too often I stop running one race to go waiting at the starting line of another.

In my mind this is the same cycle of insanity that followed my friend Melissa and I in college when we would decide that dinner would be off-campus and get in the car not knowing where we’d end up. Without direction or strong opinions on our upcoming meal we would drive in circles for an hour, passing restaurants that were “fine, if you want” and then turning back only to pass them again.

I cringe to think of the fuel we wasted with our mutual indecisiveness which was only ended when one of us would get hangry and declare “we are eating THERE!” and point to the next open restaurant.

These were the pre-Yelp struggles, my friends.

It’s harder to spot now because all of that circling and indecision and second guessing happens inside my mind.

Do you ever look ahead to all the things you want to do next month or next year and then go down the rabbit hole of planning that without actually finishing up your current projects?

Yeah, me neither.

Recently, I picked up a book from one of my favorite comedians, Jon Richardson, and was surprisingly inspired by his insights on OCD, perfectionism and the challenge of finding and executing ideal systems all throughout life.

In one passage Jon becomes distracted cleaning his flat and writes:

“I wonder what it would be like if there were actually nothing left to finish and realize that in a perverse way I am happiest when furthest from completion. When there is so much to be done, so much tidying to do at home and in my mind, I have no option but to knuckle down and get on with it, and the results of my efforts are quickly visible. The closer I get to finishing, the more vague the work becomes and actually it becomes a question of maintaining what you have rather than bettering things. Maintaining perfection is an impossible battle.”

Yes, yes, YES.

Give me a giant mess to sort or project to figure out and I’m occupied for weeks. Give me a mostly finished thing with one or two tweaks to make and eh, I’ll do that later.

How many times am I inches from the completion of a project and distracted by the next big, shiny thing?

How many unfinished and abandoned blog ideas, content drafts, free offers, podcast episodes, emails and ideas are sitting untouched on a mental shelf while I run, full force, toward the newest and best thing?

Why is starting so easy and finishing so difficult?

In many ways I wish our projects in business would operate more like a marathon. Give me a path, a goal and thousands of people to cheer me on and hand out drinks at routine intervals and I will reach the finish line every time.

Instead, projects in business can feel like a nature walk led by an inquisitive five-year-old. What’s that rock? Are mushrooms slimy? Let’s follow the bird! There’s no path, no finish line, no cheering supporters and certainly no bragging rights for finishing because how do you know when you’re actually finished and it’s not just nap time?

In the famed Kolbe personality test, most entrepreneurs will score high as a “quick start” as their primary action mode and I can understand why. We’re inspired by the possibility of change, new ideas and ways of working.

Entrepreneurs break up industries and norms, forge new paths, spit in the face of tradition and do it without 3 piece suits and corner offices. They cram 8 people into a tiny apartment and sleep in shifts, code all night, push boundaries and survive on very little sleep and too much Red Bull.

But if you’re too enthralled with the start that you never finish, things get sticky.

It often helps me to think of business problems in term of life problems. In this case, imagine sending your clothes to the laundromat and then never picking them up. Washing the dishes but somehow forgetting to do the spoons. Sending a check for that parking ticket but not adding a stamp to the envelope.

For an entrepreneur the risk and potential damage is much worse than having no clean clothes or trying to eat your cereal with a fork.

Without the successful completion of a project we’re left with open loops that hang on the subconscious and, as Richardson says, “tidying my mind” becomes impossible. There’s lost income from invoices emailed and never collected, lost opportunities from the follow up email that was never sent, lost reputation from testimonials ungathered and even missing data from the metrics never completed. And those open and unfinished projects, big and small, weigh us down even if we’re not cognizant of them.

As with most things in life, having a proper system for finishing a project is essential, maybe more so than having the perfect project in the first place. How do you know you’re done with a client, a launch, a blog or a media pitch? What needs to happen to make a project go from unfinished mess to complete?

It’ll vary from project to project but without knowing the finish line you’ll never cross it.

It’s always easier to dream than do.

Many years ago I was part of an online team that was determined to “revolutionize marketing” by creating an online program. Yes, it was going to be epic and the team quickly began discussing what modules to include. Hours went into deciding the order, when to include social media? What about classic marketing methods? Surely we start with branding. Or values. Or possibly strategy.

I could see this project was going nowhere fast and quickly bowed out only to discover six months later the team was still planning, currently with 80-odd modules “in development.”

I probably don’t have to tell you that nary a single module was launched, sold or promoted. Because instead of creating a narrow focus and executing the project from start to finish they got carried off in PlanLand for ages.

And that’s what I risk now, every moment I caress the planners in the stationary aisle at Target, look for new pens for my overflowing pen drawer or start thinking about what I should plan for summer 2019…

Stop. the. Madness.

While this trend of thinking about next year, next month, next Monday isn’t unique to entrepreneurs we need to be aware of the danger and take daily action to stop Plancrastination.

If you’re unaware of this trend then you might find yourself spinning in circles in the most mundane ways. That new diet you want to try, before the old one is done, picking out new curtains, towels and couches to keep up with the trends, always having the newest tech toy and shoving it in a drawer when something new releases.

This is what keeps me looking for a new living room chandeliers as the bulbs slowly burn out on my existing light, as I’d rather sit in semi darkness dreaming about a new light than pull out the ladder and change the bulbs.

Ever said to yourself “I can’t go for a run until I buy new workout clothes” or think that once you buy new pots and pans you’ll really try cooking at home more often?

Ever set aside a sewing project because you don’t have the perfect fabric?

Do you have stacks of DVDs or box seats that you just had to buy but sit unwatched even as the stack grows with the newest releases?

Welcome to the madness, friends!

One place this often shows up for me, where I successfully beat it back, is in relation to going to the gym.

You may not be able to tell by my arm wrestling skills, but I’m at the gym 3–4 times a week, religiously. Over Thanksgiving weekend I found myself thinking I needed to move and the intermittent rain had kept me from my usual walk through the nearby park with my dogs.

(2 dogs, 8 muddy paws, white rug, you see the problem.)

The week before I’d worked out on Monday, Wednesday, Thursday and Friday so immediately the self-sabotaging thoughts began. Let’s take a little field trip into the excuses I came up with.

Sabotaging thought: you’ve done enough, you work so hard, take a break!

While it’s true I’d gotten in 4 workouts in the previous 5 days that didn’t change the fact that I needed to move again. It wasn’t motivated by guilt or trying to win a free t-shirt, I was feeling stiff from lots of time sitting and I knew I needed to move. My brain was ready with a counter argument.

Sabotaging thought: you can do it later.

Gym appointments are on my calendar and they are sacred so I don’t skip. Plus, Monday was leg day and I always love the challenge of trying to walk without falling over after leg day.

The only way to combat this excuses was to employ an old debate strategy: do both. I can workout on Monday and today. It’s not against the rules. My brain even tried to convince me that I could workout longer tomorrow. Next month. In January. After creating the *perfect* routine. When I had more time.

But my brain wasn’t done yet.

Sabotaging thought: it’s far too late, they must be closed by now.

This excuse was throwing up all of my B.S. flags (that’s blame shifting) and despite it being pitch black outside, it was only 5:30! So I fed the dogs an early dinner, changed and went off to the gym, getting in a good workout before they closed for the evening.

I won’t treat you to all the excuses that came up while I worked out — those range from the crazy to the absurd. Because no one is really watching you workout, judging how many reps you do or observing you groove along to the music.

The point is, there’s always an excuse, a reason not to do the thing you know you need to do.

The only reason I’ve been able to counter argue against self-sabotaging thoughts that keep me from the gym is practice.

I realized that time isn’t a renewable research and I’m not getting any younger. Until those superpowers I asked for come through and give me the ability to freeze time I have to make the most of the hours and minutes I have now.

I know I can’t create change by planning to work later whether it’s on my website or planks.

I can’t build a reputation on what I’m thinking about doing.

And pushing more work onto myself in the future is not only dangerous but horrible self-care.

I’m still in the process of retraining my brain to remember that someday is not a day of the week and the only thing I can control and change is my action right now. From finishing this article to following up on an invoice or returning an email, now is the moment.

Well, not right now because it’s after midnight and my brain is slowing down but tomorrow! Yes, tomorrow.