Monday Musing: November 4th, 2019

Every two years my kids’ school hosts a huge fundraiser, a live and silent auction theme party (this year it’s Back to the 80’s) that benefits our school and parish community. I volunteered to be the chair back in 2017 because I am insane and didn’t know I would be pregnant a few months later.

After a year of hard work with a crew of amazingly generous and talented moms, this Saturday is finally the big night.

As much as it’s been occasionally frustrating and time consuming, it’s also been incredibly satisfying. I can’t believe how much I’ve enjoyed the process and what it’s done for me personally.

Monday Musings November 4, 2019Society glamourizes entrepreneurship. The idea of every day being different, having autonomy over your schedule, and the ability to make a living doing something you love is obviously appealing. Who wouldn’t want that? 

But, I’ve been an entrepreneur for 15 years. I can tell you there is a brutal dark side to it that is isolating, filled with the unknown and operates on a landscape so ever-changing it’s almost impossible not to feel like you are always three steps behind.

The last few years with this business have been challenging. I’ve had more setbacks and more failures than I care to mention. At least once a week I wanted to throw my computer across my office. 

Add to that aging (me) in this industry and feeling over-leveraged at home … I’ve been feeling increasingly defeated. 

So to be able to devote myself to something, to lead teams, see the process through, and have it be a success as given me back some of the confidence I’ve been lacking. Seeing that my efforts can result in a “win” after feeling like I was loosing for so long, was just what I needed. 

As crazy as it sounds, this experience has helped me feel purposeful again and is helping me feel reenergized. 

I’ll be showing some of the fun behind the scenes activities this week on Instagram and my 80’s look that many followers helped me put together. 

What about you? 

I’m sure there are times in all of our lives when we need that infusion of confidence. I’m shocked I found mine where I did, but as I think more about it, it makes sense. 

What about you?

How have you gained back your confidence after you felt like you lost it for a bit? 



Monday Musing: November 4th, 2019

6 thoughts on “Monday Musing: November 4th, 2019”

  1. I too have suffered a confidence level drop after retirement. Computers certainly don’t help especially as we age. They are often a source of frustration. Finding my confidence again has been a challenge as the opportunities to be in leadership positions diminish. I have joined a choir to help me find my voice again. I am on a volunteer working committee where I take responsibility and I am learning to paint and have an incredibly encouraging teacher. Finding my creativity, learning to express my self again, and a lot of positive self talk is what it takes for me. It’s an everyday task and not an easy one!

  2. I would imagine in your line of work it’s hard to find the big wins. There are probably lots of “little” wins – successful blog posts, positive feedback, etc. – but I’m guessing a lot is redundant and ongoing. Have a big, visible event with an ENDING gives me so much pride when it goes well. Kudos!

  3. I have been self employed for almost 25 years, and in the last few years it’s been really rough just to earn a poverty wage – so I get it.
    I volunteer for a community literary festival, which gives me a great deal of confidence, but also a lot of stress. It takes a lot of time that could be spent on my job – which prevents me from achieving continued success (and subsequent confidence) in that realm.
    Not sure if there is a lesson there, but I know I have to get my balance back!

  4. I worked as a freelance technical editor for many years — it was a great gig, but working at home, but definitely isolating. I’ve gradually ramped up my volunteer work for an organization that raises funds for women’s scholarships. I’m currently on the executive board for a convention for 2,000 women next spring. What a learning curve! But it is so empowering to learn new things and work as part of a team. I’m so glad to hear you feel the same way.


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