Tackling Nasty Obstacles

Courtney Kaplan
3 min readOct 11, 2023

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Getting untangled and back on track

Woman at desk surrounded by plants slowly untangles large ball of yarn one bit at a time.

Recently someone asked me, “As a coach, will you make me accountable for getting things done? Are you tough with clients?”

God, no.

We all want the magical power of something outside of ourselves to solve our problems, make us stand up straight and fly right and get our shit together.

Andy Warhol once said,

“When I think about what sort of person I would most like to have on a retainer, I think it would be a boss. A boss who could tell me what to do, because that makes everything easy…”

But if I were the task master, eventually, you’d avoid attending coaching sessions or the group meetings because you didn’t “do the thing”. Unfortunately, outside accountability quickly begins to feel like nagging or shaming. You lose the intrinsic motivation and become beholden to checking boxes for someone else which seems awesome until its a drag.

You start to avoid conversations that ask about progress on “the thing”.
Slowly “the thing”, which was once a front-and-center goal, is now tossed onto the rubbish pile.

So, how can you get past nasty tangled obstacles that block your progress?
Here’s my take.

Map the tiniest steps
Map out each tiny step and make it visible — use a whiteboard or post-its to micro-plan your mini-steps. This seems like overkill until you see this list of super-easy steps that add up to the big thing that’s been blocking you for years.

Back up and write about your project
On tough project, I create a project document in which I journal about my progress. Sounds meta, right? But it helped me see more clearly where I was in the project, how I was blocked, and what may have changed about my goals or thinking. Also, if I take an extended break, I can drop back in and remind myself how I left things.

Reward small wins
People hate this suggestion. But did you know you can train your guinea pig to do over 90 tricks? The secret is REWARDS. Guinea pigs love little treats and rewards. I know you like to believe you’re more complex than a guinea pig but….alas…you are not. (Not including a link on purpose since I am trying to talk about focus but Google it later!)

Find a group to support you
Group support can help get you unstuck, celebrate progress and provide a cadence of connection to keep you focused. You also have the fulfillment of helping someone else towards their goals as well. Subtle social pressure works.

Bring in expert support
Sometimes you’re blocked by something that’s just beyond your skill level. Get yourself majorly unstuck by finding expert support. Either invest in learning from an expert or open your wallet and pay someone to take what they do best.

Just for 5 minutes
Promise yourself you’ll work on your project for 5 minutes and stop. Set a timer and make it official. But you’ll find that you’ll probably keep going beyond the initial five minutes. (I also am a big Pomodoro fan)

Reconnect to the why
Why are you doing The Thing in the first place? Can you reconnect to the motivation and ultimate goal of why you’re taking this on? Are the reasons still aligned? Do they need some updating?

Hi, it’s me! Courtney! Two quick things!

Speaking of groups, I’m leading one with RETHINK that has been amazing. Meet with us monthly, bring your biggest challenges and get some coaching and peer advice to untangle and move forward. It’s been a fun, impactful and supportive crew. Learn more and register here. — -> Join us!

Destination Unknown(ish) — are you smack in the middle of a transition and could use some support getting through to the other side? I’m thinking about a small group to help you connect with coaching, peer support, and general good vibes. Interested? Help me pull the trigger by completing this survey!

Your coach,
CK

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