Episode 200 – Sailing Through Project Management: Lessons from the Captain

Original Air Date

Run Time

46 Minutes
Home Manage This Podcast Episode 200 – Sailing Through Project Management: Lessons from the Captain

About This Episode

Andy Crowe

Join us in celebrating 200 episodes of Manage This, as we embark on a voyage through the intersection of project management and sailing with captain and author, Andy Crowe. Andy is the founder of Velociteach and author of the best-selling textbook: The PMP Exam: How to Pass on Your First Try, he brings a wealth of experience both on the open waters and in project management. As Andy shares his insights, parallels between sailing and project management emerge, highlighting the importance of meticulous planning, effective communication, and adaptability in navigating both the ocean and complex projects.

From strategic scheduling to risk management, Andy provides firsthand accounts of how his experience as a yacht captain translates into invaluable lessons for project managers. Listeners are treated to anecdotes of overcoming tricky sailing obstacles and the critical role of communication in high-risk scenarios. Through Andy’s perspective, we delve into the delicate balance between planning and flexibility, offering practical wisdom for project managers seeking to navigate the unpredictable seas of project management. So, hoist the sails, as we embark on this enlightening journey, where the waves of the ocean meet the challenges of project management head-on.

To thank our listeners for their continued support, we’d like to offer you a special 20% discount to use towards our public enrollment bootcamps or self-paced, online training. Use promo code: 20FOR200
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Favorite Quotes from Episode

"…but a lot of the skills that I practiced as a project manager prepared me for elements of this so much. You know, thinking about good communication skills, thinking about, resource management, all of this, it matters."

Andy Crowe

"a project manager’s in a room hearing all kinds of opinions from customers or stakeholders, …and say, okay, here’s what I heard, and here’s what we don’t have to pay attention to. …that leader needs to know, who do I really need to listen to?"

Bill Yates

So this whole idea of communication, you need to know who you’re listening to and whether they know what they’re doing."

Andy Crowe

The podcast by project managers for project managers. Join us in celebrating 200 episodes of Manage This, as we embark on a voyage through the intersection of project management and sailing with captain and author, Andy Crowe. Andy is our Velociteach founder and author of the best-selling textbook: The PMP Exam: How to Pass on Your First Try, he brings a wealth of experience both on the open waters and in project management.

Table of Contents

01:33 … 200 Episodes
03:50 … An 1,800-Mile Journey
05:19 … Planning a Sailing Project
07:16 … Planning for Obstacles
08:24 … Precise Communication
11:53 … Know Who to Listen to
14:36 … Deciding Who Needs to Know
18:30 … Keeping an Even Keel
21:08 … Know Your Project
24:35 … Kevin and Kyle
25:20 … Isolation and Self-Sufficiency
28:03 … The Broken Steering System
30:23 … How to Prioritize
33:46 … A Flexible Schedule
35:21 … Managing Regulatory Compliances
37:39 … Do Your Research
43:39 … Benefits Realization for Andy
45:45 … Closing

ANDY CROWE: …but a lot of the skills that I practiced as a project manager prepared me for elements of this so much.  You know, thinking about good communication skills, thinking about, resource management, all of this, it matters. 

WENDY GROUNDS:  Welcome to Manage This, the Project Management at Sea episode.  Today we’re navigating the waters of project management with a seasoned captain at the helm.  I’m Wendy Grounds, and in today’s episode Bill Yates and I have the privilege of diving into the world of sailing with Andy Crowe, a dedicated captain who is also the founder of Velociteach and of this podcast.

BILL YATES:  Yes, he is.  It’s so fun to have Andy in the room with us in the studio.  Andy is the author of one of the most respected books that people turn to prepare for the Project Management Professional certification exam.  It’s called “The PMP Exam:  How to Pass on Your First Try.”  And that was the impetus for Velociteach.  Andy started the company in 2002 with that book.  That book has become the most trusted and authoritative volume on PMP Exam prep.  I know many of you have probably used it to pass.  Andy’s book has been reprinted 27 times in five editions and sold more than a quarter of a million copies worldwide. 

At Velociteach we offer live instruction, over 280 hours of self-paced, online education, and blogs, and podcasts.  Velociteach is a community of leaders, project managers and hardworking team members, here to support your growth and success.

200 Episodes

WENDY GROUNDS: Today marks the 200th episode of our podcast, and we couldn’t be more thrilled to have you join us for this momentous occasion. Now this is someone here who’s been at the podcast since episode one!

BILL YATES: I cannot believe two hundred episodes! That’s amazing! It’s incredible! It feels like just yesterday we started this adventure, and now here we are, reaching this incredible milestone.

WENDY GROUNDS: Yeah, and Bill you have been faithfully on every episode. Myself and Andy and Nick have jumped in and out but you have been consistent. None of this though would also have been possible without our incredible listeners. You’ve been with us every step of the way. Supporting us, sharing your thoughts, and inspiring us to keep pushing forward.

BILL YATES: That’s so true. We’ve had the privilege of interviewing some truly remarkable guests, exploring fascinating topics, interesting projects, delving into stories that we never would have known all the details of, they’ve really touched our hearts and inspired us. Today, we want to take a moment to express our gratitude to each and every one of you who has made this journey so rewarding.

WENDY GROUNDS: Yup, and the journey doesn’t stop here. In fact, this is just the beginning of what is going to be even more exciting chapters for our podcast. We have some incredible guests lined up, some thought-provoking topics to explore, and plenty of surprises in store for our listeners. Also, our folks here at Velociteach are so excited about the 200th episode of Manage This that we’re celebrating with a 20% discount off of our training products. With a limited time offer there’s a discount code for our listeners. Restrictions apply. Check out Velociteach.com, and this is for podcast listeners only.

BILL YATES: Today we’re going to ask Andy to intertwine his experiences on the open water with his expertise in project management.

WENDY GROUNDS:  So folks, grab your compass, join us as we set sail with Andy, uncovering the parallels between the open sea and the world of project management.  Andy, welcome back.  It’s really good to have you in the studio.

ANDY CROWE:  Thank you, thank you.  I’m very happy to be here today.

WENDY GROUNDS:  Yeah.  I am excited to hear the story, and to talk about project management and a yacht and how you put all of that together.

ANDY CROWE:  There’s a lot of crossover.  It’s surprising.

An 1,800-Mile Journey

BILL YATES:  Yeah.  Our understanding is you and Karen just finished an 1,800-mile journey.

ANDY CROWE:  So I just finished an 1,800-mile journey.  Karen was with me for most of it.


ANDY CROWE:  She gets credit for most of it.  But sometimes my friend Dan came down and helped me make legs of that passage around Thanksgiving and things like that.

BILL YATES:  Where did it start, and where did it end?

ANDY CROWE:  So it started at the southern tip of Grenada.  Grenada’s a long way down at the bottom of the Caribbean, eastern Caribbean, and not really that far from Venezuela.  And it’s below the hurricane belt.  So a lot of boats like to hang out there during hurricane season.  When we finished hurricane season around the first of November, we began to bring the boat back to Fort Lauderdale, which is sort of a – Atlanta’s our home, but Fort Lauderdale’s sort of a home base for the boat.  So at seven miles per hour or so, which is about the average speed you sail in this boat, it takes a while to go 1,800 miles, but we got to island hop along the way.  It was a lot of fun.

BILL YATES:  That’s nice.

ANDY CROWE:  Really a big adventure.

BILL YATES:  Yeah.  Give people an idea of the size of this boat.

ANDY CROWE:  Yeah, it’s a catamaran.  It’s 48 feet long and 25 feet wide.  Got a 75-foot mast.  So, and you’ve got to be aware of all those things.  And it draws four and a half feet under the water, so you’ve got to know that too because, when you’re coming into an anchorage or things like that, you’ve got to be aware of everything around you.  If there’s power lines overhead, that becomes very important.  If there’s rocks below, you’ve got to be aware of that.

Planning a Sailing Project

BILL YATES:  There are so many parallels with project management and being a yacht captain.  We want to get into those.  You know, the first thing that hits me is the enormous planning that has to take place.  When you’re sailing 1,800 miles, what did that take?  60 days?  Couple of months?

ANDY CROWE:  It took longer than that, but because we let it take longer than that.

BILL YATES:  Yeah, I got you, yeah.

ANDY CROWE:  And you’ve got Christmas and Thanksgiving in there, and so we wanted to be back home for those.  Bill, I’m a planner by nature.  It’s just in my DNA.  There’s all kinds of different people that do this.  And my nature, I like to plan things out.  And so there’s an upside and a downside to that.  The upside is that I’m constantly looking ahead, thinking about what’s next, thinking about risk, thinking about the scope and the timeline and costs and everything else.  The downside is, you know, those of us who are big planners can tend to live sort of in the future.  And you forget that, hey, I’m in a really beautiful spot right now, and I need to just string up a hammock and enjoy this for a little while.

BILL YATES:  Yes, yeah, you’ve got to look up for a minute and see all the different [crosstalk].

ANDY CROWE:  Oh, no, I mean, it’s true.  I remind myself of that many times throughout the journey.

BILL YATES:  That’s too good.  Yeah, there are people in your life that can help pull you out of your planning every now and then go, “Dude, look around.”

ANDY CROWE:  It’s true.  And you know, but a lot of the skills that I practiced as a project manager prepared me for elements of this so much.  You know, thinking about good communication skills, thinking about, resource management, all of this, it matters.  And I love scheduling, so I can play with that a lot.  My wife Karen and I can sit down and start planning out, okay, we know we didn’t want to go here.  We know we want to try and anchor during daylight hours.  You know, how are we going to work all of these things in so that we get there at a particular time?  And then trying to guess how fast you’ll be going based on the prevailing winds, things like that.  There’s a lot to it.

Planning for Obstacles

BILL YATES:  Mm-hmm.  And you’ve described to me before, there are project obstacles called bridges that only open during certain hours.  So you’ve got that comes into your planning, your scheduling as well.

ANDY CROWE:  You know, my friend Dan came down to help me move the boat from St. Lucia to St. Maarten, which is about a 300-mile journey.  And Karen could not make it for that trip.  And Dan’s a great mariner and a great resource to have.  So, he took over the role of first mate.  And we were leaving, but the St. Maarten Bridge opens four times a day for inbound traffic, the Simpson Bay Bridge.  And so we had to time it very, very carefully, and we were having trouble with our anchor at that point, so we couldn’t anchor outside the bridge.  We really needed to get there during opening hours.

It’s just funny, all of the things that you have to factor in.  It’s more than you would expect.  People think, oh, yeah, you’re just on a boat.  And, you know, maybe they’ve seen a show on TV that kind of romanticizes elements of it.  And it’s like, no, there’s really a lot that goes into thinking it through and making it work, making it look smooth.

Precise Communication

BILL YATES:  Talk more about communications.  There have to be so many lessons learned.  There have to be times where you went, oh, yeah, this reminds me of some of the projects I ran.

ANDY CROWE:  Oh, yeah.

BILL YATES:  And other times you’re like, this is at a whole different level.

ANDY CROWE:  I’ll tell you a funny element really quickly with communication.  We invested early on in this process in headsets, wireless Bluetooth headsets.  And boaters call them marriage savers.  Because there’s a lot of, well, there’s a saying amongst boaty people that sailing is 99% relaxation, punctuated by 1% moments of sheer terror.  And that’s true.  That is absolutely true that, whether it’s a storm coming in, or whether you’re suddenly in water that’s too shallow, or whether something just breaks – and things break on a boat all the time.  I cannot tell you how true that is.  But we invested in Bluetooth headsets so we can talk calmly to each other.

And it’s really interesting because when we’re coming into – say you’ve got a very tight docking.  Say you’re doing something that requires really careful control of the boat.  A lot of times I’ll ask Karen to go stand in our blind spot, and she’s the eyes and ears.  And I ask her to keep a steady stream of information coming at me.  Keep talking, keep talking.  When she goes quiet, I know something’s wrong.

And so you think about that before, though.  You think about I was managing a project for a bank years ago and suddenly stopped getting information from what I didn’t understand was about to be an incredibly elevated piece of work.  I just knew, you know, the guy was giving me information that everything was great.  He kept telling me, “Shrink wrap it.  It’s done, it’s done.”  It was not done.  And there was no shrink wrapping this.  We were about to be in a lot of trouble.  Well, when Karen goes quiet, I get similar vibes.  Sometimes I know something’s – something may be developing, and she’s very focused on it.  So ideally, I want somebody just talking, talking, talking.  Just keep talking.

BILL YATES:  Yeah, that’s such a fundamental truth with project management.  I think of in the alpha study that you led, one of the big takeaways, I can’t remember the alpha’s name.  Let’s say her name is Lisa.  She had set this cadence of, you know, Friday 10 a.m. I’m going to send a report.

ANDY CROWE:  Yeah,  yeah.

BILL YATES:  And she was money, man.  She just hit it.  And her customer or her manager was talking about the consistency that she had with that.  His fear, uncertainty, and doubt, that FUD factor just stayed down.  It raised during the week and then boom, 10 a.m. Friday.

ANDY CROWE:  I think she was the one, that’s been a long time since we did this study, but I think she was the one who was on a plane, an overnight plane, and had timed a status report to go out just for consistency’s sake.  And that’s, you know, nowadays WiFi is on airplanes and things like that.  But back then, Sonny, it wasn’t that way.

BILL YATES:  That was impressive.

ANDY CROWE:  It really was.

BILL YATES:  It’s like, how did she think to do that?  Yeah, yeah.  But you’re right.  I mean, human nature, especially with high-risk projects or projects that are getting into shallow waters or risky times, that’s when communication is so necessary.

Know Who to Listen to

ANDY CROWE:  Right.  Well, and the other thing, something particularly in the Caribbean, when you’re coming into a dock, and that can be, it may be a very normal docking, or it may be very tricky.  The last one I did was very tricky.  You just never know.  And when you’re coming in, a lot of times you’ll have three or four people standing around, and they all start yelling at once.  And so I have a rule with Karen.  I said, “I’m not listening to them.  I only listen to you.” 

So now she’s got to aggregate all of these, which that doesn’t necessarily play to her strength.  But she’s got to aggregate all of these different inputs, prioritize them, filter the important ones to me because otherwise, you know, my stress levels shoot through the roof.  And you don’t know.  Sometimes, sometimes you’re getting good information, and sometimes you do not get good information.  And it’s hard to tell.

BILL YATES:  Yeah.  Yeah.  You can be in a room, thinking again, a project manager’s in a room hearing all kinds of opinions from customers or stakeholders, and hopefully the team members are going to come back later and say, okay, here’s what I heard, and here’s what we don’t have to pay attention to.  We don’t have to worry about this.


BILL YATES:  We’ve already addressed this.  Or, you know, this person isn’t up to date.  And then knowing, you know, that leader needs to know, who do I really need to listen to?

ANDY CROWE:  Right.  And who knows what they’re talking about.


ANDY CROWE:  You know, my friend Dan is outstanding with distances.  So it’s really, really nice to have him on the boat.  And he’ll say, we are 20 feet and closing, 12 feet and closing, you know.  And that’s not my normal first mate’s strong suit necessarily.

BILL YATES:  It wouldn’t be mine either, yeah.

ANDY CROWE:  Right.  You know?

BILL YATES:  Less than a mile?  More than a foot, less than a mile.

ANDY CROWE:  I’m like, how many car lengths?  Just give me something.  Give me something.  So this whole idea of communication, you know, you need to know who you’re listening to and whether they know what they’re doing.  Now, we’ve done this enough, and going back to docking, we’ve been around enough dockhands.  There’s a few of them that I know, and I know I can listen to them, and they know what they’re talking about.  They know, when you’re casting lines to them, they know exactly in what order and what to do with those lines.  Some of them don’t.  You would think that everybody would, and it’s not true.  Sometimes they stand there holding the line and don’t know what to do with it, don’t know what you’re going to do.

So it’s interesting.  It’s interesting.  But communication is incredibly, incredibly important.  And that’s just in the stressful.  You know, most of sailing is very mundane when you live aboard.  It’s a lot less stressful, and communication still matters.  You know, we still have to coordinate all of these things.

Deciding Who Needs to Know

BILL YATES:  Mm-hmm.  It’s so funny.  I’m thinking back to stories that you’ve told me of some of your experiences, and like some of the long passages that you and Karen have done.


BILL YATES:  There have been periods where you have to take shifts.

ANDY CROWE:  Yeah, yeah, yeah.

BILL YATES:  You know, you sleep, and I’ve got eyes and ears on everything, and then we switch.  And you both have a code.  You both have realized there are certain events or certain risks where I need to, you know, wake up the crew.  It’s all hands on deck kind of thing.  And I think of with projects, for the project manager that’s hitting that alarm too soon and drawing the whole team in.  It’s like whiplash for them; right?  You know, they’re just like, wow, you know, what’s going on?

ANDY CROWE:  Right.  Everyone doesn’t need to be exposed to everything.

BILL YATES:  Yeah, yeah, yeah.  You know, I see that with people that are earlier in their career.  They don’t have that figured out yet.  And they think, oh, I need everybody looking at this with me.  We’ve got to solve this problem.  It’s urgent.  And then they find out, oh, that wasn’t so urgent.  That could have waited.

ANDY CROWE:  You know, we’re I guess in year six now, if I’m doing my math right.  And early on, that was very much our experience, that we wanted each other to be looking at every single thing and kind of checking, doing sanity checks.  And now it’s so nice to know, if Karen’s at the helm temporarily, that I don’t have to worry.  I know her judgment.  We’ve seen so many things that I don’t have to wonder if she’s going to make a bad call or whatever.  And there’s no scenario where I want somebody to let me sleep through a crisis.  If I’m resting, get me up.

BILL YATES:  Yeah, yeah.

ANDY CROWE:  If you need to get me up, get me up.  Yes.  We had a weird situation on a recent passage where you would be surprised – actually, it’s not just surprising, it’s shocking how frequently you are about to intersect with another vessel in the middle of the ocean.  You’ve got this vast ocean, and all of a sudden here’s somebody, and if you don’t do something, you’re going to hit them or come very close.  And there’s enormous number of right-of-way rules and all of that.  But, you know, you can guess based on the size of the vessel and some of those things whether or not that vessel’s aware.  But you don’t always know if they know the rules, and they understand how this works.

So, we had a crossing that we had to go from Fajardo, Puerto Rico, which is on the eastern side of Puerto Rico, to Providenciales, Turks, and Caicos.  And we timed it out, and I predicted it was going to take 72 hours.  But you’re way offshore, you know, way, way offshore.  And we started making this crossing, and we started having meeting situation after meeting situation with boats.  You know, again, that’s something that my wife as the first mate knows the rules.  She understands how those work.  But as captain, you’re responsible, full stop, for everything that goes on. 

So, there were a few where she’s having to get me up and say, “Hey, wait a minute.  We should have right-of-way.  We should be the stand-on vessel in this case.  But they’re not seeming to do it, and I’ve tried to hail them on this channel, and blah, blah, blah.”  So, then you get involved and start making judgment calls.

But yeah, 72 hours, I think it took us 68, so we did a little bit better than planned.  But it’s three hours on and three hours off, and you’re going 24/7.  The risk really in a situation like that is you’ve got this enormous piece of canvas up.  And as long as the weather stays predictable – and the Caribbean’s very, usually very consistent.  You can kind of set your watch by which way the winds are going to be blowing.  The trade winds go through there, and they’re coming from the east.  And so, you can predict all that.  But then they’re predictable until they’re not.  You know?  And then you’ve got this enormous sail up that has a mind of its own.  That can be a little bit scary.

Keeping an Even Keel

BILL YATES:  I want to hear a little bit more about how you deal with risks like that that occur because I’m thinking of some of our project managers who they’ll hit those periods of the project where people are working a lot of overtime.  Maybe they’re not getting a lot of sleep.  Maybe they have a passage in their project similar to this where, you know, I’m on, I’m off, I’m on, I’m off.  I don’t even know what day it is anymore.  I remember you and I talking about the travel we used to do, and it was like, I can’t remember what state I’m in.  You know, you’re in the hotel, and you call down, “Where am I?”  It’s kind of embarrassing, but it’s like, I’m traveling too much.  There are times in our projects that are a bit like that.

How do you and your crew, and your project team, how do you guys keep an even keel?  How do you know when you’re about to hit that threshold of becoming dangerous?  And how do you go, “Okay, now is the time.  I recognize it in myself, or I recognize it in you.  Let’s have a transparent conversation and go, we need to stop.”

ANDY CROWE:  Right.  I tend to obsess about some elements of this, like the weather and certain maintenance aspects on the boat.  I will do a deep dive on the weather.  We’ve got some great tools that will forecast what the winds are going to be doing, what the seas are going to be doing, if there’s going to be rain, if there’s going to be lightning.  Had a bad encounter with lightning years ago that I don’t want to repeat.  So, I pay attention to all those things.

BILL YATES:  So you’re checking those risks.  You’re trying to anticipate those hard times.

ANDY CROWE:  Oh, I’m mapping out those risks nonstop.  There are plenty of times where we will plan an anchorage based on which way the winds and seas are going to be worked up.  We’ll pick the anchorage, and we’ll just hide out for a couple of days, wait till things settle back, you know, get more normal or calm down.  Yeah, definitely.  And then there’s – it’s interesting, Bill.  There’s maintenance stuff that you have to do, a lot of stuff.  Just the marine environment is tough on a boat.  And so there’s engines that are constantly needing babying.

And, you know, we blew a radiator hose on this last passage and didn’t have a spare.  So, you have to get very creative in how you deal with that situation; you know?  Keep the engine going, and trying to cut out the bad part and splice it together, and it’s just trickier.  Whereas if you’re home, you know, you just go pick up another radiator hose.  But no.  So, then it gets you thoughtful.  Boaters have kind of a generous list of spares that they keep on board.  And for whatever reason, I didn’t have a spare radiator hose.  I should have.  But, you know, you add that to your risk register going forward.  I do now.

Know Your Project

BILL YATES:  That’s it.  I think of early in my career I was managing projects with this particular type of software.  And I was naive.  I was thinking, I really don’t have to know the inner workings of the software.  I don’t have to get that deep into the code.  That’s up to the, you know, the pure software guys, the computer guys.  They’re doing that.  I’m kind of the liaison here.  I’m the project manager.  I don’t have to go too deep technically.  Until something breaks, or until somebody calls in sick, or you’re at the customer’s site.  Your IT support’s not there with you, and something ain’t working. 

So I can relate to that.  I think there are times when, early in my career, I kind of fooled myself thinking, I don’t have to know that list of spares.  I don’t have to know how this engine works.  Until it breaks, and I’m the only one that can fix it.

ANDY CROWE:  If you go back to around maybe the late ‘90s, year 2000, there was this movement in the project management world that a PM didn’t need to be a domain expert.


ANDY CROWE:  And that took on a nearly religious fervor amongst practitioners that they really liked this, that now project management becomes its own sort of profession and its own domain, and that you’re a project manager, and you have business analysts to do all of this stuff, and you have technical teams to do all this.  I can tell you after spending a career as a project manager that the more you as a PM know about a particular domain, the better off you will be regardless.  And so, I mean, yes, that extends to captaining a boat as you might guess; you know.  But I’m not a believer in this idea of, oh, I’m just a project manager, and I can manage any kind of project.  Yeah, let me know how that goes for you.


ANDY CROWE:  When somebody’s telling you to shrink wrap a piece of software that sucked.  And you don’t have the technical ability to necessarily, now, that’s not exactly the way that went.  But you know, I went to engine school in New Jersey, Somerset, New Jersey, to learn how to take this thing apart, these big diesel engines.  And that’s something that I did not have any training in formally.  And now we got in there and started diving into the deep end of that pool really quickly and spent several days out of our comfort zone, well, at least out of mine, I can tell you that.  But it really was transformative for me.

And so now, this is just random, but one of the things that matters on a boat is the sounds, the sounds that engines are making, the sounds the sails are making.  You can tell when things are okay.  Every system has this particular set of sounds.  And that becomes so important to me.  But again, those are things that you develop over time, and it’s expertise.  And it may not translate to another domain, or it might.  You never know.

BILL YATES:  Yeah, yeah.  That’s so funny.  I’m thinking of the phrase “agile smells.”

ANDY CROWE:  Yeah, yeah, yeah, yeah.

BILL YATES:  It’s like, okay, you kind of get a sense for when the team’s clicking along.


BILL YATES:  And then something doesn’t smell right, you’re like, okay, what’s off?

ANDY CROWE:  No, that’s exactly, exactly the way it is.  And sound becomes incredibly important to me.  And my happiest moments are when there are no engines running, there’s no generator running.  We’ve got solar power recharging the boat’s house batteries.  We’ve got sails generating our velocity.  And, you know, those are good times.

Kevin and Kyle

KYLE CROWE: Velociteach is an award-winning project management training company founded by Andy Crowe, author of The PMP Exam: How to Pass on Your First Try. This book has become one of the most respected books worldwide on the PMP exam.

KEVIN RONEY: You can prepare for your PMP and PMI-ACP exams. With our Velociteach exam prep bootcamps, we offer a comprehensive, accelerated learning program that includes live instruction from subject matter experts and all the study tools needed to pass these rigorous exams.   Take a look at our SELF STUDY, SELF-PACED ONLINE, or LIVE INSTRUCTOR-LED class offerings.

KYLE CROWE: Knowing what to study should be effortless. That’s where Velociteach can help! Easy to read, easy to understand, exactly what you need to pass.   And with the Velociteach no-risk guarantee:  Get Certified or Get Your Money Back!

Isolation and Self-Sufficiency

WENDY GROUNDS:  Andy, I’m just thinking about spending such a long time on the boat, just the two of you, you and Karen.  You’re in a remote place, or you’re just in the middle of the ocean.  Do you ever feel isolated?  And you only have yourself to count on, if something goes wrong.  You have to be really self-sufficient.  So how have you countered that?

ANDY CROWE:  Yeah, no, it’s definitely true.  One passage that stands out was, when COVID kind of hit its peak, the Caribbean shut down, and we had to sail 1,100 miles nonstop from St. John back to the U.S.  And that was, well, St. John is the U.S., but still it’s not the mainland.  So as we were doing that, you know, we had to prepare.  We had to think through resource management.  And then you’re exactly right.  We lost an engine underway that we had a problem.  And it was a problem that at that point in time I could not fix.  So that was pre-engine school.  That was one of the motivators; okay?  I don’t want this to happen again.

But we lost an engine.  And so then, you know, you’re out there.  You’re bobbing up and down in the ocean, and it’s just you and your first mate.  And there’s nobody that’s going to come help you.  There’s no way to get in touch with anybody who can come help you.  Realistically, we do have an emergency beacon that I guess, you know, we could activate if we had to, but that’s sort of a nuclear option.  Then you’re getting helicopters and rescue boats, you hope.

So it’s interesting.  The isolation, Wendy, it’s funny.  The isolation to me is one of the more appealing parts sometimes.  You can just be away.  You can unplug.  But it gets intense when you are 100, 200 miles offshore.  There’s no land in sight.  There’s no vessels in sight.  And there’s no airplanes flying overhead.  And you have to keep the boat going, you know, you have to be able to handle problems as they come up.  You’ve got to take care of the safety and security of your crew.  You’ve got to make sure everybody can stay fed.  Hey, we fish, and we’ve had very good luck with that.  That’s been kind of fun.  I wasn’t a huge fisherman before this; but, boy, I enjoy it now.

So yeah, the isolation and the self-sufficiency, this boat is made for that kind of passage.  But still the amount of planning that goes into it is intense.  And God bless my wife for taking a careful look at provisions and thinking through menu planning and, you know, here’s what we need, and here’s what we have room for, and here’s what we have refrigeration for, and boom, boom, boom.

The Broken Steering System

ANDY CROWE:  One of the, I guess one of the most alarming things that happened to us – and goodness, there’s a list, you know.  But our steering system broke in the Atlantic in between Hilton Head Island and Charleston.  We were headed from Hilton Head to Charleston.  And we heard this strange noise – again, back to sounds – and the steering got really easy.  The wheel got really easy to turn.  And I was unclear on what was going on.  I opened up a cabinet, and all of these chains and cables and pulleys had just collapsed.  They were in the floor.  And this was a system I didn’t have any experience with.  I had seen it.  I barely understood it.  And now, you know, we couldn’t steer the boat.

Well, there’s an emergency, it’s called an “emergency tiller,” and it’s a bar that you shove in at the stern of the boat, and you can sort of leverage.  And I got us close enough to land that I could get a cell signal, and I called a guy I affectionately refer to as my sensei.  He knows everything, every inch of that boat.  He’s just a really, really good resource.  And I called him, and thank goodness he answered.  Told him what had happened.  And he walked me through a multi-step, multi-hour process for resuscitating this enough to get back to Charleston.  It was really crazy.  And you know, that emergency tiller in the rear, I can’t think of anything more physically taxing.

BILL YATES:  Yeah, I was picturing, I mean, how much does the sailboat, how much does it weigh?

ANDY CROWE:  So it’s 38 tons.


ANDY CROWE:  So you’re dealing with almost 80,000 pounds.  It’s a very heavy piece of equipment.  I didn’t understand.  I knew about the emergency tiller.  And I knew where it was, I knew what it was, and I knew what it was for.  Never once thought that I might actually need to use it.  And then once I did activate it and get back there, I realized this is not something I could do for any length of time.  This is awful.  You know?  And certainly, you don’t have easy, fine control.  A wave comes in and hits the rudders, and it yanks it out of you.  You know, you’re lucky not to go in the water.  So it’s no fun.

How to Prioritize

WENDY GROUNDS:  Andy, you told us you’re a planner, and I guess you have to prioritize how you’re planning, what tasks you’re doing.  So, when you’re setting on a journey, how do you prioritize?  What’s top of your list?

ANDY CROWE:  Yeah, top of my list is always going to be weather and conditions.  Always.  And it’s funny because you can have good winds, favorable winds, and unfavorable seas.  It’s unusual, but it does happen.  And I’ve made that mistake before and said, “Oh, the winds look great.  Let’s go,” and then regretted that.  So, I spend a lot of attention and time getting the right weather window and making sure. 

Otherwise, it’s going to be bad for everybody.  Then, you know, you’ve got fuel management, things like that.  If you’re able to run your engines, then you want to make sure that you’re not going to get in trouble, depending on the length of the passage.  We pay a lot of attention to this is how long we’re going to go.  We’re going to try and anchor.  We’re going to try and anchor in daylight hours, ideally.  All of these types of things.

So no, I do, and I’m sort of fanatical about maintenance, and especially with engines and things like that.  There’s regular maintenance you do almost every day on an engine, and I will do that a lot of times the night before a passage just to have everything ready, make sure that we’re in good shape for it.  So yeah.  But Wendy, clearly weather is the big one on a sailboat.  The big cruise ships, I don’t think they think about it the same way.  I know it matters to them, but it doesn’t matter the same way, and that’s a huge one for me.

BILL YATES:  Weather is – it’s humbling. And it’s something we can’t control.  And I think for many project managers, they have to, on the construction side especially, they have to come to terms with that and just treat it like another risk and know, okay, this is top of my list in terms of my planning.

ANDY CROWE:  Yeah, I don’t think of it as just another risk because you’re so exposed to it on a sailboat.  You’re so impacted by it in so many ways.  So, it is the big risk.  And it’s funny, there’s a saying that I like that the most dangerous thing to have aboard a sailboat is a calendar.  You don’t try and sail to a schedule if you can help it.  So, you know, if you have to be in Puerto Rico on a particular date, you may well get in trouble.  That’s a tricky passage, passage there called the Anegada Passage that’s infamous, really difficult, and you have to time it just so.  If you are meeting friends there, or you have a flight booked, ask me how I know, you can really get into trouble.


ANDY CROWE:  So, weather becomes not just another risk.  You’re so in touch with it and so impacted by it that it becomes everything.

BILL YATES:  Yeah, yeah, yeah.  I’m thinking of project managers that are wired like you and I are who want a plan, and they want – man, they want it in ink.  Okay, this is the day we’re going to be in Puerto Rico, or this is the day we’re going to launch this next phase of the product.  But they have a customer, let’s call the customer “Weather,” that brings another dynamic.  You know, the customer says, “Oh, this is so awesome.  I know I identified the top eight requirements. And I just identified two more.  I just was on my competitor’s website, and now I’ve got two more requirements I want to add to this.”


A Flexible Schedule

BILL YATES:  In terms of being flexible as a project manager, because I love having a plan from A to Z, and Z is not going to move, how has sailing helped you embrace a whole ‘nother level of flexibility in terms of your schedule?

ANDY CROWE:  Yeah, it’s changed me.  It truly has.  Now, I think Karen is more naturally – she’s more Type B.  She’s more in the moment.  And I’m the one that’s, you know, got all of the maps and charts out and planning and thinking about where and when and how long and looking at weather and things like that. 

We tell each other, two or three times a week we remind each other, hey, we’re going to be flexible.  We’re on a sailboat.  You’ll go insane if you’re wired like I am, and you’re constantly trying to stick to a schedule and because there are too many variables out of your control, really an astonishing number.  So, it’s best to be in the moment, to relax.  Now, that doesn’t always translate to the way I manage projects, you know?  But it’s the reality.  You are so impacted by your environment and things out of your control when you’re on the water that there’s no good option.

BILL YATES:  Yeah.  I think for some project leaders they need to hear that and go, okay.  Looking back on it, there’s some projects where my customer said, “These are the top requirements I want to hit,” and they stick to it.  And there are others where, boy, they were just wired differently.  They wanted to change things up, and I wasn’t willing to.


BILL YATES:  And maybe I could have had better results if I’d been more open to change.

ANDY CROWE:  Well, that’s a good – that’s a good way of looking at it.

Managing Regulatory Compliances

WENDY GROUNDS:  You are dealing with many different small islands, different regulations.  Each one has their own rules, and you’re passing through.  So how do you deal with that, with the maritime regulations, international standards, and all of those regulatory compliances that you have to adapt to?

ANDY CROWE:  Right.  Yeah, there’s a couple of things there.  There’s a big framework for maritime law.  And I went through a process of getting my captain’s license, getting my 100-ton master’s license.  You get schooled in that law very, very thoroughly and then tested very comprehensively.  And it’s everything from, look, what are you allowed to dump overboard?  You know, you’ve got a chicken bone, can you throw that in?  You got a cup of used oil, can you toss that in?  No.  You know, so there’s a lot to know.  And it would probably surprise you what you are allowed to put in the water, but the ocean’s a big place, and what it can handle and what it can’t.  So there’s things like that.

And then each island does have their own rules and their own paperwork requirements.  And in the Caribbean, which I have grown to love, there are some islands that you go to, and you’ll go to Customs and Immigration to check in, and they may be there, and they may not.  They may be coming back this afternoon, and they may not.  You got to kind of learn sort of what to expect.  There are wonderful books that are resources on this kind of thing that will tell you what to expect and kind of how to prepare.  So, we go in hopefully pretty well armed in terms of how to navigate that.

The marine regulations, you know, they get rather intense, and it covers everything from what I was saying earlier about intersecting with another boat, and who gets out of whose way, and in what circumstances, all the way down to, you know, safety and security of your deck crew, and how to take care of people, and what you’re allowed to do as a captain, and what you’re not allowed to do.  There’s quite a comprehensive lot of things to learn there.  But it’s been good.  You know, the more, Bill, back to our conversation about domain expertise, the more I’ve learned, the more at ease I’ve become.

Do Your Research

BILL YATES:  You and Karen have done tremendous research, too, I know, as you were getting into this.  Looking back on it now, you probably think it was the tip of the iceberg.  But you were finding blogs, you were finding writers and other people that have been there, done that, that you were able to find out, okay, what should I expect when I hit this island?

ANDY CROWE:  Yeah, well, so this is the trick.  Most of these, and there’s YouTube channels that get out there, but what they’re doing is they’re sort of selling a fantasy, and they don’t show the gritty aspects of having to climb down into a hot engine bilge and deal with some problem.  And you’re cramped, and you’re trying to not get burned while you’re trying to troubleshoot.  They don’t show that very often.  They show people frolicking in beautiful waters.  And that’s part of it.  It’s part.  But it’s all mixed together; you know?

So yeah, I feel like the blogs we read and the YouTube channels that we watched before we started this put sort of an unrealistic element in my mind.  And then you get out there, and you get exposed to what it really is.  Now, it turns out I am wired for that.  I love the maintenance and the fixing and all of that stuff.  But a lot of people give up this life very quickly because of that.  So on our blog, which is SailingWithGratitude.com, we try and tell the whole unvarnished truth. 

We don’t do a lot of video, a little bit.  But we try and just tell what it is because somebody, somewhere, is going to google something that puts them there, and maybe it’ll help.  Maybe they’ll see how we had to navigate solving a problem or how we had to figure something out.  That’s part of it.

BILL YATES:  It’s so interesting.  I think even at Velociteach, I just reached out to the instructors the other day.  I’m going to be teaching a class, and it’s the first time I’ll be at the location for this customer, this client.  And a couple of guys have been teaching there, so I was asking them, hey, how do you get in?  You know, they have security badges.  Do they have to meet you and escort you in?  What hotels should you stay in?  Is it walking distance?  Just some of those logistics.

And some of our project managers are, you know, they’re dealing with different cultures.  They’re dealing with different time zones, different compliance, different laws and regulations.  And there’s so much research they need to do in asking multiple sources, like you guys found.  You know, there are some sources that were spot on; others were fantasy land.  And trying to find out, okay, when we show up in Peru and meet with the customer, are we going to have everything that we need?  You know?

ANDY CROWE:  Absolutely.  You know, and it reminded me when you were telling that, I spoke two or three years ago at the Federal Reserve in Atlanta.  Getting into that facility, I was unprepared.  I had no idea what I was in for, and how difficult, and how many checkpoints there were in the security.

BILL YATES:  Yeah, mm-hmm.

ANDY CROWE:  And, you know, they’re looking through every compartment in the car and running mirrors under my car to look, I guess, for explosives or something.  And it was an intense experience.  And I almost didn’t make it in time for my talk because I didn’t factor that in.

BILL YATES:  I just spoke last week at a healthcare facility.  And I didn’t think about the regulations walking into that.


BILL YATES:  And I’ve got PowerPoint on my laptop that I’m planning on using for the presentation.  And then it was a bit of a, “Ho ho, whoa, whoa, whoa.  Let’s talk about that.”  You know, “I don’t need to be on your network.  I don’t have a flash drive, I promise.”  You know, there are projects where you show up assuming you’ll have access to a network or assuming you’ll have access to files of the customer, that kind of thing.  No, you can’t even bring your laptop in here.

ANDY CROWE:  Right.  Well, and it’s funny, back to the Caribbean, how many places, restaurants, customs offices, immigration facilities, all of this that have signs, enormous signs that are highlighted on the door that say, “If you’re not wearing a mask, you may not enter.”  But then you go in, and nobody’s wearing a mask.  You know, so there was a period of time where that was true.  But over and over you see that where, no, you can’t come in here without a mask.  And then I’m thinking, oh, every time I think, oh no, I don’t have a mask with me anymore; you know?  I’ve got to figure this out.

BILL YATES:  It’s so funny, Andy, I’m thinking back.  You shared a story with me.  This was before you started Velociteach.  You were doing consulting with a company, and you guys showed up with the wrong equipment.  It was equipment of a competitor, and they gave you a look like, yeah, you’re not coming in here with that.

ANDY CROWE:  Oh.  Yeah, no, I’ll tell that story.  We showed up to work with Dell, and we didn’t have Dell laptops.  And they asked us to leave.  And yeah, it really surprised me.  I was just a dude at this point in my career.  I wasn’t anybody special. And I walk in there with the wrong laptop, and they were like, “Yeah, you’re going to be leaving.”


ANDY CROWE:  And this was a decent sized company that I was working for.  They had just done a technology refresh maybe a year earlier.  We’d all gotten new laptops of a different brand.  And so, yeah, no, it’s a funny story now, you know, and it makes me very aware, you know, that, hey, there’s sensitivities you better be tuned into.

BILL YATES:  Yes, there are.  Yeah, I was up in New York walking into Pepsi Bottling Group.


BILL YATES:  And I had to be careful what kind of beverage container I had with me.

ANDY CROWE:  Yeah, no joke.  I worked for Coca-Cola for years, and they take brand loyalty extremely seriously.  There’s no joking or laughing if you walk in with a Pepsi bottle.


ANDY CROWE:  They don’t like that.

BILL YATES:  It’s like the best thing I could do for not just our project team members, but our organization was to give them a heads-up, too. 


BILL YATES:  You know, it was like, “Okay, I just got slapped.  I don’t want you to make this mistake, too.”  So, you know, communicating that back to them.

ANDY CROWE:  I like it.

Benefits Realization for Andy

WENDY GROUNDS:  So we recently did a podcast on benefits realization; and how, when you finish your project, have you realized the benefits?  So how do you feel?  Have you found that sweet spot?  Are you living and realizing the benefits of your sailing?

ANDY CROWE:  Wendy, this adventure, and I don’t know how long it’ll last.  You know, when I started it, I negotiated with my wife that we would do this for two years.  And now we’re…

WENDY GROUNDS:  I remember that.

ANDY CROWE:  Now we’re in year six.  She says one year, but I think it was two.  I should have gotten it in writing.  And now we’re early in year six.  Now we’ve got a grandbaby on the way.  Now we’ve got a lot of other things.  And so I don’t know how much longer I could continue to pull this off.  But the benefits for me are that it’s changed me, and it’s changed me in some interesting ways.  And one of those has been to learn to be flexible.  That is not how I’m wired.  So, I’ve had to learn to be flexible.

Another is I didn’t know that I loved working on engines.  I just didn’t understand that about myself.  And now I do.  And now, you know, it’s not like I’ll do anything, but I know my limits.  So if I can work on something, I enjoy doing it.  And if not, okay, I’ll turn it over to somebody who knows what they’re doing.  So yeah, I think in addition to some great photos and some cool stories and all of that, it really has changed me pretty profoundly.  That’s the benefit.

BILL YATES:  Andy, there are so many lessons learned from the life that you’re living right now where you’re running the company and also running a ship.  This sailing adventure you guys have been on, like you say, it’s been life-changing.  There have been some phenomenal lessons that have taken your approach to projects and all the challenges that come with them and gone, “Huh, okay, there’s something, something new.”  You’re always learning, always growing, and I appreciate your attitude that you’ve had throughout this sailing adventure.  Thanks for sharing that with us today.

ANDY CROWE:  Okay, thank you, Bill.  Thank you, Wendy.


WENDY GROUNDS:  Here’s to 200 episodes of conversations, learning, and inspiration, and to many more to come! Thank you all for being part of this incredible journey with us.

You can visit us at Velociteach.com, where you can subscribe to this podcast and see a complete transcript of the show.  You’ve also earned your free PDUs by listening to this podcast.  To claim them, go to Velociteach.com, choose Manage This Podcast from the top of the page, click the button that says Claim PDUs, and click through the steps.  And until next time, remember to stay curious, stay inspired, and keep tuning in to Manage This! 


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