in entrepreneurship

The Highs and Lows of Doing Work That Matters

Every success. Every client you sign on. Every successful project you complete. Every check you put in the bank. Every award you win. Every milestone you achieve. Matters immensely.

Every failure. Every stumble. Every time you know you could have done better. Every time the client decides unicorns and awkward ethnically-diverse stock photos WOULD make their website look better. Matters immensely.

As an entrepreneur, it’s natural an inevitable to put an incredible amount of stock into everything you do. When I worked a “traditional” nine to five – I never felt how I do now about my work – my successes and my failures. And honestly, at times, I’m envious of how I used to be able to detach emotionally from the daily grind.

There have been more tears than I’d care to admit. Wondering where I went wrong. Wondering what I could have done better. Worrying and doubting.

But for every tear has been a smile, a laugh, a celebratory happy hour with colleagues and friends. A client who has described working together as “life changing”. 

This line of work, my friends, will tear you down and test your will. But it will also make you feel more validated, more alive, more in control, than you ever thought possible.

It’s a roller-coaster. A journey in which everything must be taken in stride. The highest of the highs and the lowest of the lows. Some you’ll be prepared for, and some, no matter how hard you try, you’ll never see coming.

Successful entrepreneurs understand that the highs and lows cannot be avoided. They put their hands up and stay buckled in. They endure. And they enjoy the ride.

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  1. I completely agree with this. One night, I’m crying and thinking my business wont work, and the next morning, something awesome happens. I’m a huge believer in working your tail off, so that’s what I try to do. Each day brings different challenges for sure!
    Budget Blonde

    • Success is grounded in hard work. The hustle. Doing more than the other guy. Trying harder. I am a firm believer in that. They’ll be plenty of ups and downs, that’s for sure – but at the end of the day, it’s totally worth it. Thanks for coming by, Cat!

  2. Enjoyed the reminder(s) of why I love doing what I do and who I do it with almost every single day. Not easy, not always simple but damn sure inspiring and satisfying. Thanks!

  3. Killer post man, reminds me of the quote below. It’s so easy to get caught looking back or forwards that we miss what’s really going on.

    “Man surprised me most about humanity.Because he sacrifices his health in order to make money. Then he sacrifices money to recuperate his health.And then he is so anxious about the future that he does not enjoy the present; the result being that he does not live in the present or the future; he lives as if he is never going to die, and then dies having never really lived.”

    ― Dalai Lama XIV

    • Dang it, posted the above reply under the wrong article. My bad.

      Loved this post as well though. Have you ever read “The War of Art” by Steven Pressfield? He talks a lot about “Turning Pro” where your internal fortitude is strong enough to withstand the rollercoaster ride of doing your art. Really great read!