Welcome to Give It Another Go

What is this blog all about? Well, let me tell you...

FURNITURECAREER FLIPSLIFE LESSONS

Jenny Dempsey

1/7/20262 min read

Hi. I’m Jenny.

I’m the person who will happily pull a beat-up dresser out of an alley, knock off all the spiders, toss it in the back of my Rav4 only to spend every Sunday sanding it in my San Diego garage.

I’m also the person who got laid off from my startup tech job in 2022 after 16 years in the industry, questioned her entire career, started learning how to restore furniture by watching YouTube videos, hosted a podcast about career change (The Career Flipper) to learn how people actually did this, took on a new corporate job 2 years later to pay the bills while I build a furniture restoration business on the side and learned (the hard way) that life almost never moves in a straight line.

This blog exists because I needed a place to put all of that.

I’ve always loved writing. I was an English major. I focused on creative writing and even studied abroad in Ireland, sipping Guinness in a pub while writing poetry homework. And let's get real: my middle name is basically "TMI". I wear my heart on my sleeve and am not afraid to show up authentically and vulnerably. Instagram captions and TikTok clips are fun, but they’re not always big enough for the stories I want to tell: the messy ones, the quiet ones, the ones that take a few paragraphs to land. And also, I just write a lot!

So this is that space. Welcome!

Give It Another Go is a collection of stories about second chances: for furniture, for careers, and for people. It’s about what happens when something (or someone) is written off too soon. It’s about the courage it takes to try again, even when you’re not sure how it’ll turn out.

Yes, you’ll find my furniture stories here. Pieces pulled from curbs and alleys that still had good bones, good energy, and more life left in them.

But you’ll also find stories about things I'm learning, and people I'm talking to who are inspiring me to keep chugging along. Things like:

  • changing direction when the old path stops working

  • rebuilding confidence after feeling unwanted or out of place

  • creative risks, quiet reinventions, and slow growth

  • moments when giving up felt easier than giving it another go — and what happened next

This blog is for anyone who’s ever looked at something broken, unfinished, or overlooked and thought, maybe there’s still something here.

It’s also for anyone who’s ever felt that way about themselves.

My hope is that this becomes more than just a blog. I want it to feel like a place where you recognize yourself, where you feel less alone, and where you’re reminded that starting over doesn’t mean starting from scratch.

Sometimes it just means giving it another go.

I’m really glad you’re here.