Breaking the “cage”

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“Jobs fill your pocket but adventure feeds your soul”. Here in lies the the great mystery … how do we fill our pockets to be able to obtain the adventure? Or do we just take the plunge and jump in with both feet and say to hell with the pocket filling? Our (somewhat lofty) goal is to be able to quit our jobs in 5 years and sail from the Great Lakes to the Caribbean. Have we lost our minds? Maybe … but we’d love to take everyone on the adventure with us so welcome to our insanity!

Honestly, this Type-A control freak can’t even begin to grasp the second of the options. No way. We MUST have a plan! But how full do our pockets need to be in order to take the plunge? Nick and I aren’t afraid of a little risk. But both of us have had our “rock bottom” moments in life and we will both do anything to avoid going back there. We have immersed ourselves with a slew of blogs, YouTube videos, books and sailing information to prepare our budgets.

Our days have become this lovely dance of work for income and work for the dream. We both have jobs that we love (mine in Marketing … Nick’s as a chef) so we are blessed to have a clear driven mindset when it comes to our goals. The challenge for us currently is learning additional income producing skills that will help sustain us when out at sea. I already have somewhat of a knowledge of social media marketing from my current and past careers but I’m learning about so many other avenues and it’s very exciting! Some great ideas are …

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  • Blogging/Journaling – This one seems to be the go-to for most liveaboard lifestylers. It is definitely a great way to not only document your sailing adventures but share them with others! Some of the more established sites also include merchandise that they have created to sell with their boat name, logo and brand. The biggest obstacle with any internet site while sailing seems to be finding a WiFi signal to be able to conduct business. Hotels, Cafes, Restaurants and Bars seem to be the best options to look for to catch a signal.
  • YouTube videos – These are our favorites to follow and definitely a possibility for us in the near future! So much good content and education to be found in the YouTube world! For an income generating viewpoint we would need to invest in a waterproof travel camera of some kind and possibly some editing software. Oh yeah … and actually become comfortable in front of the camera! (Yikes!) Once a following is created a Patreon or similar account can be attached to help generate income.
  • Write a book – A friend has suggested Amazon Publisher to me as a great side-hustle job. While you may not see great revenue from the first book (it may take several books to build a following and income) it seems like an exciting option to explore! Adventure and travel … meeting interesting people in exotic locations … who knows; We may just be the next Hemmingway! Click here to educate yourself on the process, fees, etc … https://kdp.amazon.com/en_US/help/topic/G200635650
  • Learn a helpful skill – Are you great with mechanics or construction? Do you know how to work with fiberglass, sew or paint? If not are you willing to learn? Just like any community, word gets around when someone has a skill that is needed by others. Help mending sails or repairing boat mechanics is always in need and can help bring in some additional cash or trade when out at sea!
  • Chartering Business – While this is definitely an eventual business goal for Nick and I, we will have to do more research on start-up costs, insurance, laws and restrictions, etc. before jumping into these waters. Entrepreneur.com states the average fees to starting a boat charter business can be anywhere from $10,000-$50,000 (https://www.entrepreneur.com/businessideas/boat-charters). Although with Nick’s skills as a chef and my love of hosting it would be an amazing way to make some money and share our dreams with people!

What ideas do you have for generating a great side-hustle? Let us know in the comments below!

***Affiliate Disclosure ***

Land2Shore LLC participates in various affiliate marketing programs, which means we may get paid commissions on editorially chosen products purchased through our links to retailer sites. Our editorial content is not influenced by any affiliate partnerships, and all opinions expressed here are our own.  Photos of the experiences featured in our blogs are taken by Nico and Kirsten during our adventures. 

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Picture of Kirsten Hoskins and Nico Rossi

Kirsten Hoskins and Nico Rossi

Hello Friend!
Originally from the Midwest, Nico is a professional fine dining chef and Kirsten is a full-time blogger/digital marketer. In 2020 we decided to reinvent ourselves in the beautiful Florida Keys and have not looked back!

Consider us your friends to bounce questions to about travel ideas, lifestyle, vacation locations, food or things to do in the Florida Keys and we'll be sure to answer through email or post.

Let's explore together!

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Land2Shore LLC participates in various affiliate marketing programs, which means we may get paid commissions on editorially chosen products purchased through our links to retailer