Home Advice For The Young At Heart How To Leave The Job You Hate And Live Your Dream

How To Leave The Job You Hate And Live Your Dream



by Howard T. Scott, author of “Rascal on the Run

Do you ever feel like you’re on a treadmill with no purpose and no end in sight? I can relate. Twenty years ago, I reached my jumping off point and walked out of a courtroom for the last time. I had spent more than two decades in practice, and I knew I couldn’t do it anymore. I didn’t just decide to leave on a whim, though. The legal profession was all I knew. My father and grandfather were lawyers, and I got my start in my teens, working in my dad’s law office. But, over time, I took stock of the increasingly dismal state of affairs my colleagues and I faced. A once-noble profession had morphed into an advertising game. I was staring down the barrel of alcoholism and depression. So, I left.

Now, I can be found sailing around the Caribbean and writing books. My life is exactly the way I want it, simple and beautiful. How did I do it? Like any good lawyer, I drafted a plan.

Always have multiple streams of income

I made an excellent living as an attorney. I mean, I was really good! But, what wasn’t good was the constant stress and nagging feeling that my job was killing me. I knew I needed to somehow fund my escape, so I began by investing in real estate while I was still working. I thought of it as a safety net, and I didn’t touch it until I needed it. When I finally set out on the high seas in my yacht, the Capricho, I was glad to have that security.

Hopping off the corporate ladder is the perfect time to learn the art of the side hustle. When I left my lucrative career behind and set sail, I went into it open to any unconventional job or freelance gig that came my way. Every dollar earned helped sustain my freedom.

Turn your passions into paying jobs

Making a fresh start after leaving the rat race is your ticket to discover the possibilities of your talents. You say you get a charge out of decorating? Start right now on getting your interior design certificate and launch your own business. Apply the same theory to pet sitting, professional landscaping, cleaning – you name it. You’ve been doing it all this time just for fun, so why not turn it into income? You may not earn as much as you did at your day job, but you’ll be happy

The Joneses? Never heard of ‘em

It’s so easy to get caught up in the game of appearances. The better you do, the higher the stakes get, right? Fancy houses, cars, and exclusive country club memberships are prizes in a competition you can never win, and all of a sudden you realize you’re knocking yourself out to attain things you won’t ever have time to enjoy. Who are you doing it for? Finding the courage to break that cycle feels good, and so does casting off the expectations of others. The Joneses really don’t matter that much after all. 

Hold tight to your hobbies

While you should be proactive about picking up income wherever you can, keep in mind that not all passions can be monetized, and that’s a good thing. It’s crucial that you prioritize hobbies like reading, crafting, biking, geocaching, yoga or whatever else you do to stay anchored and sane as you navigate the next chapter of your life. These are the things that keep you grounded, the actions that make you love yourself. Engaging in them regularly is also an excellent way to network with like-minded people who share your vision.

Sometimes these hobbies can lead you to your next big opportunity. I had always dreamed of writing novels, but I never had the time. When I finally left my law practice and embarked on a sailing adventure, I grabbed my chance. I wrote my novel, Rascal on the Run, while island hopping, and no one was more surprised than me when it was picked up by a publisher! The old adage is true: You never know until you try.

Self-care is a real thing. Look out for you.

Something tells me if you’re reading this, you’re probably already feeling the need to do something new. Making a clean break is scary, but one of its healthiest benefits is the luxury of not caring what perceptions people hold of you. This is your time to concentrate on what makes you feel alive. It’s your time to go where the current takes you. You are the captain of your own destiny.


After thirty years of practicing law in Georgia, Howard T. Scott pivoted from the courtroom to writing fiction inspired by anecdotes from the southern storytelling tradition he’s immersed in. He’s one of the founding partners of the Legendary Rhythm & Blues Cruise — the world’s only fully chartered blues cruise — and a lover of live music, fitness, nature, historic preservation and travel. Rascal on the Run is his first novel.