Goal Guilt & High-Fiving Happiness

The first 20 seconds or so when you wake up are quite possibly the most blissful of the day. For a moment you forget where you are, maybe even who you are, and as your brain boots up, you slowly start to remember. With that remembering comes an influx of reminders from your conscious mind - the day’s agenda items, to-do’s, and the anxiety of what lies ahead of you for the next 15 hours or so.

I love my life. Like, more than I ever have before. But since quitting my day job and becoming a full-time entrepreneur, the thoughts that follow the blissful first 20 seconds each morning have become increasingly loud and urgent. When you alone are responsible for your business’ success and failures, every moment counts. I was never under the illusion that being my own boss would be easy, in fact, “The Career Experiment” was originally called, “Don’t Quit Your Day Job: Finding Happiness Without Going Solo” and adamantly dissuaded people from thinking that working for themselves would be the answer to their career unhappiness.

Despite my realistic perspective on what being my own boss would be like, I didn’t anticipate the overwhelming feelings of guilt that would come along with the freedom to steer my professional ship in whatever direction I choose. No matter what, you could always be doing more. There’s always a business stone unturned, someone you could be meeting with, and a digital marketing tactic you could be using. Even if you’re using all of your waking hours as efficiently as one human can be expected to, the guilt lingers.

The guilt is not entirely focused toward unrealized business opportunities either. Half of the guilt I feel goes toward not feeling appreciative enough for everything wonderful that’s happening both in my business and my personal life. High-performers, Type-A’s, and most entrepreneurs often forget that there’s a gestational period from the birth of an idea to the completion and success of it. I left my day job five months ago last week, and in that time an insane amount of great things have come to fruition. However, while the ideas, hopes, and dreams of yesterday are being realized, new ones are forming constantly. It’s the ones in the middle of the gestational period that tug at your shirttail, demanding your attention and inflicting those feelings of never being able to get it all done.

Right now, the ideas, hopes, and dreams I conceived years ago are being born. Two years ago today, I posted to Facebook that I wanted to start teaching workshops and speaking more professionally, and tomorrow I get on a plane and fly to Austin to speak at the Create + Cultivate SXSW pop-up to a crowd of hundreds of people. I’m filled with excitement, nervousness, and anticipation, but also a teeny bit of guilt for feeling overwhelmed by the sheer number of things on my to-do list and not appreciating the good stuff enough.

When you’re in the middle of a swirling storm of stuff happening (good, bad, and neither), it can be hard to appreciate the joy and excitement of seeing your ideas, hopes, and dreams finally come into being. If you don’t stop and revel in the completion of those things as they happen, there’s literally no point in doing any of it, and the guilt associated with ignoring them is never worth it. So, as I pack my bag to head out of town for the fourth weekend in a row to go do something I put out into the universe that I wanted to do years ago, I’m going to do as my dear friend Maxie does and be “batshit grateful” for all of it.

Even if you’re not an entrepreneur, the lesson stands. Don’t keep pushing ahead day after day and be so focused on the future that you forget to notice your present. The good stuff happening in your life today was what past you longed for, so do them a solid and revel in the completion of their dreams. Happiness and success aren’t finish lines to be crossed, they’re the running buddy alongside of you throughout the race, handing you water and cheering you on. Give them a high-five today, won’t you?


Baily Hancock is a Multi-Passionate entrepreneur who answers to the call of any of the following: Collaboration Consultant, the Career Experiment Founder, Speaker/Workshop Leader, and most recently, Co-Founder of inex women.

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