Sail Loot Podcast 025: Peaks and Troughs of Sailing, Life, and Money

By on July 17, 2015

Where do I start?

I’m posting this because I’ve been re-inspired and I have decided that maybe I should share a few things that have been going on in my personal life.

I actually have Andy Schell to thank for that. Yes, I produce some podcasts, but I also enjoy listening to other podcasts, especially if they have something to do with sailing. The 59 degrees North Podcast hosted by Andy Schell is one of them and I recently picked it back up and started listening again.

The first episode that I found, titled “Ups and Downs”, is about the ups and downs of starting a sailing business. I then rewound, and started back in February, where I had left off with the 59-North podcasts. I noticed in these episodes that Andy was sharing some fairly personal thoughts, emotions, and feelings.

I also wrote an article and recorded it for a podcast called, “Sail Loot Podcast 007: To Hell With Keywords, Be Yourself First”. So here I am, following my own advice, and being myself first.

What’s Been Going On?

Wow, this is actually really hard to say.

I think I just have to spit it out.

Unfortunately, Megan and I are getting a divorce.

I was shocked, just as you may be now. In January we were happily looking for sailboats (or so I thought). In February she didn’t want to continue our relationship as husband and wife. I came to find out a few weeks later that she had started having a relationship with another man.

It’s a little cliché. He’s the trainer at the gym at her work that teaches the boot camp she’s been going to every morning. I’ve met him on a few occasions. He’s one of the people that she did an adventure race with, and trained for that adventure race with.

I don’t mean to bash Megan here, or say that it’s all her fault. My therapist says that I probably tell people this is how it happened in order to get some sympathy. Maybe I do. He also says that’s okay.

These are also the facts. These things did happen, and I wish that nobody ever has to go through a similar experience.

I’m not sitting here saying that there aren’t things that I could have done better. I could have. But what I’ve come to find out is that nobody’s perfect, and I don’t believe that I ever broke a vow the way she did.

So, Enough of All That. What Have I Been Spending my Time Doing?

Somehow we got through a week in Ireland for a wedding even though it all started more than a month earlier. Here I am at Cliffs of Moher 4-13-15

Somehow we got through a week in Ireland for a wedding even though it all started more than a month earlier. Here I am at Cliffs of Moher 4-13-15

Umphrey's McGee St. Augustine, FL 4-10-15

Umphrey’s McGee St. Augustine, FL 4-10-15

Ribs & Rythm Festival with best of friends 4-11-15

Ribs & Rythm Festival with best of friends 4-11-15

  • I tried to work on us for a while. Work on our relationship. Make things better. Win her back.
  • Couples couseling.
  • Therapy.
  • Lawyer counseling.
  • Lots of conversations with the most awesome group of friends and family that a guy could ever have. If you’re listening, you know who you are. I love you and thank you so much more than I think you can ever comprehend. That’s what brings me to tears. The joy in the fact that there are people in this world that you can always turn to, will always help you out, and will be there no matter what. I would do the same for them, and we all know it.
  • I’ve been working on myself physically. After all, I can’t just let this model for male sexiness break down and turn to crap.
  • I’ve been working on myself emotionally. You know those awesome friends and family that I just talked about? Yep, they really are amazing.
  • The spring and summer also bring activities, music festivals, green trees for amazing hikes, warmer water to allow myself and Barley to cool down after those hikes, and more amazing people out and about and enjoying what nature has to offer.
  • It also brings Wednesday evening sailing races. Over the winter, those races are mostly on the weekends. After all, it’s already dark at 7pm on a Wednesday night in the winter. My least busy day of the work week is Wednesday, and during the Winter I was putting together the interviews, and show notes, and blog posts, and podcasts on Wednesdays. Sometimes I would work on them until 10 or 11 in the evening. Now, I have to leave the house around 5pm to get to the lake by 5:45pm, help rig the boat, and sail until 9 or 10pm.
  • I’ve tried to work on myself intellectually, and that usually involves trying to learn something about sailing, or something about small business so that I might be able to get myself on the water sooner rather than later.
  • I’ve also been trying to work on myself spiritually. I’m a terrible Catholic, but for me, getting out into nature, getting onto the water, and experiencing more and more of this beautiful world and the people and cultures that share it seems to re-energize my spirit.
Sailboats Racing in St. Augustine 4-11-15

Sailboats Racing in St. Augustine 4-11-15

Morning Beer after the Sweetwater 420 Festival 5k.

Morning Beer after the Sweetwater 420 Festival 5k.

Sweetwater 420 Festival

Sweetwater 420 Festival

Oh yeah, the engine mounts broke on the Jeep. I had to order a super beefed up bracket and mount and replace.

Oh yeah, the engine mounts broke on the Jeep. I had to order a super beefed up bracket and mount and replace.

Wednesday night Sailing Sunset Races on Lake Lanier.

Wednesday night Sailing Sunset Races on Lake Lanier.

More Umphrey's at the Counterpoint Music Festival 2015.

More Umphrey’s at the Counterpoint Music Festival 2015.

More Wednesday night  Sailing on Lake Lanier

More Wednesday night Sailing on Lake Lanier

What’s next? What’s my plan?

All I can do right now, or the next logical step that I can think of, is to get all of the legal and financial aspects of all of this done and out of the way in the most efficient manner possible.

Some of that will end up being beneficial for me. I’m not sure if this will make me sound like an asshole, but I won’t have to help pay off the $100,000 of Megan’s student loans anymore.

We are also selling our house. You can add general contractor to the list of things that I’ve been doing. Our realtor hired a “stager” to stage our house for sale. The stager suggested that the house go through a very minor re-fit. All it took was some paint in the kitchen, paint in the master bath, and paint in one of the bedrooms, some carpet cleaning, some carpet installation, removing some furniture, and adding some decorative items. 

Anybody want to buy a house in NE Atlanta?

Anybody want to buy a house in NE Atlanta?

Fortunately we bought the house at exactly the right time. We were just re-zoned in October of 2014 to a better school district. We will be listing the house for $85,000 more than what we bought it for. As far as cash goes, we will also be getting the money that we put down for a down payment on the house. After realtor fees, and closing costs I’m hoping that we will have $100,000 to $125,000 to split. Personally, I’ll hopefully be getting a check for about $50,000 to $62,500.

I’m not really sure how much I should be sharing our financial situation, but I like asking about numbers, so it would be a little hypocritical of me if I didn’t tell you about my numbers wouldn’t it?

I also have a townhouse in the Atlanta area that I’ve been renting out for the last 2 years. I haven’t made much money on it after keeping up with the mortgage, Home Owners Association dues, realtor fees, and taxes, but at least I’ve come out about even.

The townhouse is mine. I bought it before Megan and I were married or even dating or engaged. The current lease is up on July 31, 2015. For now, I will move back in, and hopefully, I’ll be able to refinance and save some money every month on the mortgage payment.

As far as finances go, it’s not a terrible situation to be in.

The big question is…what do I do with my life and my finances? I’m a 36 year old single dude with no kids, no college education to save for, and will soon have a little bit of loot in the kitty.

Of course, my first thought is…sailing money. But what should my plan of attack be? This is where my mind goes crazy with about 5 million ideas. Do I just take off and start traveling, sailing, and cruising now? Do I get a few more certifications, learn a few more things, get stuff a little more set up and take off in a year or three? Maybe I travel Southeast Asia for a little while. I want to keep this whole Sail Loot thing going too. Who knows?

Should I open a trading account and see if I can make a little money in the market? Maybe I’ll be able to, “Live on The Margin.”

Should I move to the islands and find a job at a SCUBA shop, or sailing school, or marina, or sailing camp?

Should I use some of the money to invest in starting a business? Should I invest more in Sail Loot and really get things going?

Once the house is sold and I’m back in my townhouse I’ll probably have enough money to pay cash for a decent cruising sailboat.

Tasha and Ryan from Turf to Surf are selling Hideaway, the sailboat that they’ve used to cruise down the East coast of the U.S. and into the Caribbean with. Congrats to Tasha and Ryan who sold their ESL school business and are moving on to bigger and better things (and sailboats of course)!

Bill and Trisha are selling Wanderer, the sailboat that they’ve been sailing around the Florida Keys and the Bahamas for the last couple of years. Congrats to Bill and Trisha! They are expecting a little one soon!

Mike and Rebecca are selling Zero to Cruising. They’ve sailed this PDQ catamaran from Canada down to Trinidad.

There are a few issues with the plan of just going ahead and buying a sailboat to cruise the world and taking off. First, I’m an engineer, and not only will I purchase the boat, but I will certainly want to make sure that I know everything about all of the systems, and that I have all of the systems that I need in good working order. Does that mean re-fit or installation of some of those necessary systems? I know, I know, Thomas Fuller once said, “He that will not sail till all dangers are over must never put to sea.” However, let’s take a look at the scenario:

  • I currently live in Atlanta, GA. Atlanta, GA is at least a 5 hour drive from salt water, or the coast.
  • If I purchase a sailboat with the cash that I acquire, I will probably use most of that sail loot.
  • My plan has always been, and always will be to shake the boat down, and re-fit.
  • Did I mention that I currently live in Atlanta, GA and that’s at least 5 hours from the coast?
  • It seems as if my plan for the first year or two should be to move to the coast with enough cash to buy a sailboat, and enough extra cash to live on it, do a re-fit (if necessary), maintain it, and make sure my sailing skills are where they need to be to cruise. This would certainly allow me some more access to the sailors on the dock for some Sail Loot podcast interviews!
  • However, dockage and maintenance alone could cost $20,000 or more a year depending on the boat. Andy Schell threw out a number of $50,000 a year for the Swan 48 he just bought on one of the recent 59 Degrees North Podcasts. I don’t have that extra money lying around right now.
  • Another option would be to secure a job in a location on or close enough to the coast to live on or own a sailboat that I can sail and work on on the weekends.
  • Plea to all listeners…if you have a job opening that you need to fill on or around the coast where I can live on or own a sailboat…I’m sharp, level headed, and well rounded. I’m a Georgia Tech graduate with a Mechanical Engineering degree, but I’ve been working in a medical technology field for about 8 years. I obviously know a thing or two about websites, podcasts, social media, sailing, and boats, and I’m a super quick learner. You can fire me an email at

So, what would I have to take care of prior to leaving Atlanta?

I would either have to sell the townhouse, or rent it out. Renting it out could be cool, but my Home Owners Association has a rule about too many units being rental units. I know, I told you that my townhouse is currently rented, and it is. I was able to weasel my way into securing a 2-year hardship rental agreement with the HOA. That hardship rental agreement is done on July 31st, the end of the current lease. I’m 6th on the waiting list to be able to rent out my townhouse. I started at 15th back in March of 2012. It may be a few years before the HOA allows me to rent my townhouse, but with the housing market picking back up a lot of owners that are currently renting, or on the waiting list, may start selling.

I would have to save enough money to re-fit and maintain a sailboat and live for several years, or find another source of income (or both), and quit my current job.

Quitting my current job is inevitable at some point down the road. The issue is that I’m very loyal. I’m the first person that the owner hired. You may even call me the Vice President of this small medical technology business. I’ve known the owner since I started school at Georgia Tech in 1997. For those of you that don’t want to do math, that’s 18 years. In our business, giving 2 weeks notice, and actually walking away in 2 weeks could be detrimental to the business. I would have to give enough notice so that he could find a way to cover all of the cases with all of the surgeons that we work with. At the same time, if I have a conversation with him about wanting to follow my dreams and explore the world, and I give him enough time, he may be super excited for me and ask me what I’m waiting for. After all, he and his wife are members of that group of family and friends that I talked about earlier.

This could very well be my Sailboat on Lake Lanier very soon.

This could very well be my Sailboat on Lake Lanier very soon.

Of course, for that other source of income, a job on the coast is fine, but what am I doing here with Sail Loot? Don’t get me wrong, the primary purpose of Sail Loot is to inspire people to follow their dreams, connect with people and the sailing community, ask the questions about sailing money that everyone wants to know, share those answers, and maybe even teach.

Speaking of connecting with people, I got an awesome Facebook message from Adam Wieser a few days ago. He said,

Hey Teddy. I’m Adam. Firstly, I’d like to thank you for taking your time to do this podcast. I have even learned to create a webpage because of sail loot. Sail loot is by far the best source of information on the financial side of cruising anywhere. I (and apparently many others who have the cruising dream) have only been on motorboats and actually don’t know how to sail. I love that some of your guests started out like me with only a dream and no sailing knowledge. I can’t thank you enough for that because it reminds me that the dream is possible even for a sailing noob. I live in Chicago and think it might be a good idea to walk the docks on days the yacht club has races and try to get on a boat as rail meat just to learn a little and get on the water. Secondly, I started podcast 11 and my eyes lit up when I heard “Umphrey’s McGee”. Umphrey’s is one of my favorite bands as well. That New Years show was a heater!! Thanks again for everything you do to inspire, inform, and keep dreams alive. UMPH Love, Adam

I wrote him back and said,

Adam, All I can really say is…Thank you. It’s freaking awesome that you’ve created a webpage, and that Sail Loot was the how/why. Have you created one? If so, what is the domain name? It’s seriously messages like this that pull me back in, remind me, and inspire me to keep Sail Loot rolling. It’s really all about meeting and connecting with people like you who’ve got similar dreams and interests be it boating, sailing, sports, and/or music like Umphrey’s McGee! What’s the last show you went to? What is your next? Are you going to the Dead show? Lastly, do you mind if I use your message as an example in an article/podcast? Thank you for letting me do what I do. Cheers! Teddy

And he wrote back,

Teddy, Please feel free to use the message. I would be honored. I have not created a website yet but I’ve watched the blue host 10 minute website video and never thought it could be so easy.(better believe I’ll use your blue host link when I finally purchase a domain) I’m still brainstorming what the main content for my website will be. I’m thinking about a local music blog and I’d like to combine it with a podcast, similar to sail loot. As a musician I have gigged all around Chicago and know a lot of other gigging musicians/bands to interview. I also have recording equipment so a podcast should be easy peazy. I saw Umphrey’s over Memorial Day weekend at summercamp. The Godboner set with UM and Gene ween was a spectacle. Next Um shows for me are in Peoria June 28th then probably rivinia in August. I unfortunately was unable to score any GD50 tickets but I’ll be down there listening for sure. Plus Kung fu is playing a late night July 4th that I’ll probably end up at. Kung fu rocks! What shows are in your future? There is so much good music out there. On the sailing front, I’ve had my eye on a dinghy sailboat to learn on. My only issue now is the man selling it is not selling the trailer too. I think if I buy it and have him drop it in my back yard my motivation to get a trailer will go up exponentially. Thanks again for all your hard work and the content you provide. You truly are doing all of us listeners a service. Until next time, Adam

This is the perfect example of what Sail Loot is all about. Inspiring and reminding people that “the dream is possible even for a sailing noob.” and hearing things like, “I have learned to create a webpage because of sail loot.” Then, there’s even a common connection with music interests.

He goes on to say, “better believe I’ll use your blue host link when I finally purchase a domain.” Granted, it’s more like purchasing hosting, but enough with the technical details. It reminds me of a hair brained idea that I had a few months ago. What if I put together a week to 10 day sailing trip where I taught people how to build their websites, blogs, podcasts, online media channels, and online portion of their businesses?

When I was learning to sail we would wake up at 7am because it was beautiful outside. We would make some coffee in the galley, have some breakfast, maybe even go for a morning snorkel prior to starting our “class time” at 8am.

Morning class time would last an hour or two, and then we would set sail to our lunch destination. At lunch we would snorkel, explore, and maybe have a short sailing class for 30 minutes to an hour.

Next it was another few hours sailing to the next island, bay, anchorage, or mooring field. We would drop the hook or grab a mooring ball, make a rum drink, and have a little more class time before more rum drinks, and some dinner.

Instead of having sailing classes, why couldn’t we have website building, social media growing, podcast creating, online marketing, business classes? I could take 6 to 7 people out on a sailboat for a week to 10 days. We could have websites set up and running on the first morning. You may have a small business that you want to build a website for.  You may want to start your sailing blog. You may want to start a charter business, charter your sailboat, and put a website together for it. Maybe Sail Loot becomes the go-to website building business for the charter sailboats of the Caribbean. Who knows?

I’m obviously throwing out some hair brained ideas. Maybe your reading this and thinking, “I can learn these things online from home. Why do I have to spend money and charter a sailboat with you to learn how to set up my website.” The short answer is…you don’t. It would be fun though. It would be a pretty awesome vacation and you’d learn something all at the same time. You’d have 24-7 access to ask me anything that you want about websites, social media, online business, sailing, my personal life, or whatever else for 7 to 10 straight days. I kind of think of it as a mini seminar that takes place on a sailboat.

If you are interested. If you don’t think that this mini seminar on a sailboat is such a hair brained idea, then send me an email at and let me know.

I love all of you. I thank all of you. Thank you so much for helping spread the Loot Love.

If you listened to the podcast and you’re wondering, everything went fine with the surgery and I’m recovering quickly. I think I’ll be able to SCUBA dive again on August 26, 2015!

Links and Resources From This Episode:


Thank you very much for listening to the show! If you enjoyed listening, it has helped you in any way, or you know somebody else that would enjoy it, please share it using the social media buttons that you see on the page.

Additionally, reviews for the Sail Loot podcast on iTunes are extremely helpful and greatly appreciated! They do matter in the rankings of the show and I read each and every one!

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About Teddy

I am a 37 year old that just wants to find a way to make a remote income, gather some Sail Loot and cruise the world! I have been sailing for a couple of years now, but mostly on 10 day trips as vacationing crew. I just recently took sailing to the next level by completing my Basic Keelboat, Basic Cruising, and Bareboat Cruising Certifications! I am also Vice President of a Medical Consulting Company, have a Mechanical Engineering degree from Georgia Tech, and have taken several Coding, Computing, and Online Business courses. It's time to share what I have learned!


  1. RobertM

    July 17, 2015 at 9:44 pm

    Hi Teddy,

    I’m so sorry to hear about what you’re going through. Know this though, life will be better without her. People do grow apart and stuff like this happens to almost everyone. Luckily, you are young and there are plenty of woman in Atlanta that would be proud to have you as a boyfriend.

    The best advice I can give after 60 years of living is go take a break down in Florida and do a lot of sailing.

    Do I just take off and start traveling, sailing, and cruising now?
    Do you have the money to do that?

    Do I get a few more certifications, learn a few more things, get stuff a little more set up and take off in a year or three?
    Think about it on your vacation, be realistic, make a plan and then stick to it. You’ve got a lot to think about, buy small now and wing it? Wait a while and but bigger and make it more permanent? Move to the coast and get a job? Move to coast and don’t get a job? Keep the townhouse or sell?

    Maybe I travel Southeast Asia for a little while.
    I would say no (but I don’t know you). Save your money for a nice boat when you’re ready.

    I want to keep this whole Sail Loot thing going too. Who knows?
    You should. It takes years to build an audience. You’ve got a great start.

    Should I open a trading account and see if I can make a little money in the market?
    Absolutely NOT!

    Should I move to the islands and find a job at a SCUBA shop, or sailing school, or marina, or sailing camp?
    If it floats your boat, sure. I have had about 25 different jobs in my life and I don’t really regret any of them. I have a lot of skills now. You can do anything you put your mind to.

    Should I use some of the money to invest in starting a business?
    I would say no. Most small businesses fail…learned that the hard way a few times. That is unless you have a million dollar idea and a lot of skills like the Active Captain story.

    Should I invest more in Sail Loot and really get things going? All you need for SailLoot to succeed is content. Content is king. I have done SEO work and all you really need to do (other than the basic SEO stuff) is update often.

    I am in Alpharetta if you want to grab a beer and talk.

    • Teddy


      July 20, 2015 at 5:26 pm


      Thank you. AND…a fellow Atlanta area dweller! I may just schedule a Sail Loot meet up or something soon. I’ve been talking to a few people from the area.

      I agree with a lot of your answers. I’m not making any rash decisions this second, but pondering the decisions that I’ll be able to make once the house sells.


  2. Matt B

    July 19, 2015 at 4:18 am

    G’day Teddy

    First time poster, but long time lurker of the Sail Loot podcast.

    Sorry to hear your news. I really hope that there might be some silver lining out of this (although it may take several years to become clear).

    I’m glad that you’ll continue with the podcast. It’s a great resource for all of us dreaming of a cruising lifestyle – and I hope it might be therapeutic (or at least a good distraction) at this difficult time.

    Cheers – and thanks for your great work on Sail Loot.


    • Teddy


      July 20, 2015 at 5:18 pm

      G’day to you as well! Thank you. Yes, Sail Loot will continue and it is therapeutic.


  3. Leah

    July 20, 2015 at 2:28 pm

    Teddy I’m super sorry to hear about the personal storms you’re going through… that can’t be easy, especially while keeping Sail Loot up and running and trying to figure out your next steps!

    But would it be crass to say NOW YOU’RE FREE TO PURSUE YOUR DREAMS?? Because that’s my natural instinct for you :)

    Quick random thoughts/ideas for you:
    – 6 months working, 6 months sailing — works especially well if you live near the coast
    – Living on a sailboat can be cheap. We’re paying $400/month in moorage (“rent”) to live in the heart of the city… and that includes electricity!
    – There are always people looking for crew — now might be the time to take on some interesting crewing opportunities
    – Sail Loot is an amazing resource (I’ve made some new friends thanks to you and our little podcast!) so please make this a continued part of your future!! I’m thinking Kindle book (“How to fund your dream: 67 real-world accounts from people that cut the lines”), patreon possibilities, more website building… sky’s the limit!

    As always, let me know if I can help in any way. Life is too short to say later, and winter sucks.

    Leah :)

    • Teddy


      July 20, 2015 at 5:21 pm

      LOL. I love it. You’re right. Maybe only one more winter in the cold (and it doesn’t even get THAT cold here in Atlanta).

      Thank you.


      • Teddy


        July 20, 2015 at 5:28 pm

        Oh, and don’t you worry, Sail Loot will continue. That is the only thing that I know for sure right now. Sail Loot will sail on!


  4. Ken

    July 21, 2015 at 1:39 am

    First of all, thanks for your podcast. I look forward to each one and it helps me kill the time until I can “sail away”.
    It may sound strange, but I’m kinda of jealous….Not about the divorce of course, that is a tough go, but I believe all things happen for a reason and you will be stronger for it. I am jealous of all the possibilities and options that you have been presented with. Focus on those possibilities and I am sure you will make all the right choices.
    Only you can say what the right choice will be, but I, given the right circumstances, would be headed to the coast and buying a boat. You are young and well educated and I am sure a job could be found. Just a thought but what about designing and installing boat electrical systems. At the very least I am sure there are many cruisers/sailors/boaters who could use help and guidance in that area.
    Whatever you decide, know that you have many loyal listeners who are cheering you on. Thanks for your honesty and your passion!

  5. Kasey Nesselrotte

    July 25, 2015 at 10:15 am


    I felt compelled to respond and give you my well wishes for this next chapter of your life. There isn’t much that I can say about the divorce that hasn’t already been said but you are now in a unique position of being able to craft your life in any which way you choose.

    I’m going through a divorce myself (for the last 2 years) but the separation was of my choosing. I have now found someone that her goals line up with my own and I have never been happier. She wants to sail full time even more than I do. We currently spend 2-4 weekends a month sailing in the Gulf of Mexico on our Hunter 26 with plans to buy a larger boat to live on. We both have come to the conclusion that we could never see ourselves as the land locked, cul-de-sac, howdy neighbor, sort of people and luckily for us we both have very supportive parents to fall back on.

    So for now we are trying to figure out how to get our sail loot (because we do not make or have a lot of money), buy a bigger boat, cruise the Caribbean, juggle her family and my children, and most of all be happy and enjoy life.

    This brings me to your podcast and why I love it so much. The transparency you provide is refreshing to someone who sometimes just wants to get to the “how they did it.”

    I must admit i’m jealous of the position you have placed yourself in with regards to all the amazing people you have met. Life is funny sometimes and you never know how a friend you make can alter the direction of your life. A friend that my girlfriend and I made resulted in trips to their house in Marsh Harbour, sailing with them on their lagoon catamaran, and coming into possession of our hunter 26 and a smaller O’day daysailor 17. Amazing people.

    So keep your head up and remember that good things come to good people. Thanks for putting the time and effort into this podcast.


  6. Moose

    August 1, 2015 at 2:10 am

    Hi Teddy, I am a Sail loot pod cast listener and have been since episode 001 funnily enough. (I have been following the adventures of the S/V Delos crew for a while now and thats what led me to your podcast).

    I was really sorry to hear the news. The logical thing to do would be to keep your job for another 6 months to a year, lower your living expenses drastically, and save as much money as you can to give yourself as much runway as possible. In your spare time, focus on exploring and building Sail loot or other sources of passive income.

    Having said that, personally, I would want a change to disconnect myself from the old life and give myself a change of environment and a change of circles so that not only are you focused on thinking ahead and dealing with these new challenges, but none of it reminds you of the past. Meet new people, make more friends, and make new memories .. if you decide you want to begin a new relationship, it might be easier too.

    You know your boss. Decide if you can have a heart to heart with him and tell him your goals. Maybe tell him you will work a couple of more months to meet current obligations but would like to take 6 months or a year off to clear your head. Even better would be if you could tell him exactly what you were planning to do, and that if all else fails you would appreciate it if he could keep your job (or similar position) open for you based on your loyalty and hard work all these years. 18 years is a very long time.

    Life is quite literally too short. It does not cost too much to live on a sailboat… outside the US it costs even less. I dont know much about the Caribbean but Mexico is really cheap. You have less tying you down and less to fear about than you ever have at this point. In addition to interviewing other folks, you will be able to share how YOU are going about learning and making your dreams happen. Ofcourse, it wont all be smooth sailing, but that is kind of the point. Adventure without risk is disneyland.

    Remember to balance the logical thing to do (which is exactly what you have been doing so far) with your emotional needs as well. If you feel you have a handle on it, then stick with the logical thing.. otherwise, go start afresh.

  7. Lisa Dorenfest

    August 5, 2015 at 4:20 am

    Hi Teddy,

    I am really sorry to hear about your marriage to Megan ending but the good news is that there are so many wonderful possibilities waiting for you. Moose gives very wise advice and you are generating so many wonderful ideas that I don’t have much more to add…. except one suggestion. When you get everything settled (or maybe while you are settling things) why not try doing some sailing passages as crew. Great way to travel. And you have this HUGE network of sailors to tap into to hitchhike your way to various places on other people’s sailboats. You can always buy one later. Just an idea that has worked well for me.

    And as my father always says when shit hits the fan like this ‘What an Opportunity’. When he gives me that advice right after I feel like I’ve been kicked in the teeth and am spiraling downward I think ‘”F” that noise’ but in the end, I’ve always found that he is right.

    I’ll close by saying that I am impressed and moved by your honesty in this post. I look forward to watching you ascent from the ashes!

  8. Lisa Dorenfest

    August 5, 2015 at 4:30 am

    Oops, just listened to the intro to your podcast (had only read the blog post when I wrote my comment). I see you are considering my recommendation already. Good. Do it. You’ll love it.

  9. Pingback: Inspiration

  10. Lisa Dorenfest

    August 5, 2015 at 7:38 am

    I was so moved by your post that I have reblogged it on my blog.

  11. Phil-Fulub

    February 16, 2016 at 9:57 pm

    I had the same age as you when I got through my divorce. You will survive and go through it.
    Go sailing, hope on a boat.
    Here is my advice:
    Do not by a boat yet. Anyhow, single handling a boat is a lot of work and there ways to enjoy sailing around the world.

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