It’s Always Sunny

My wife Twyla planned a dream vacation to Hawaii for our tenth wedding anniversary. It was like a 10-12 day trip, and most of it would be spent on a cruise boat going from island to island. Almost every night, while we ate dinner, adventure and slept, the ship would move on to different ports across the Hawaiian Islands. We would have breakfast, rent a car, explore till around dinner time, return to the ship, and repeat the pattern in a new port the next day. It was a fantastic trip but one that almost got de-railed on the first day. The drama of that day would create a motto that now not only governs my family but has informed my leadership ever since. That motto is, it’s always sunny in Lahaina.

On our first full day of adventures, after getting on the boat in Honolulu the night before. We were on the Island of Maui and had plans to spend the day in the city of Lahaina. We were going to go to the beach, eat some yummy food and attend an authentic Hawaiian Luau. As a bonus, Twyla had booked us a jeep where the top could come off. It was a huge surprise to me and was intended to be the cherry on a fantastic day… then came the rain.

It just started to pour, and a thick fog had rolled through the part of the island we were on. See, we had to drive to Lahaina from where the cruise boat had docked. We also only had some printed google maps and some basic information. We had cells phones, but the plans were way too much for us to have data back then. So we couldn’t just look up the weather or easily make other plans. As the rain poured, the drama picked up in the car.

There were tears, arguing, hunger grumps, frustrations, wanting to call it quits, talk of the vacation being ruined, and it was only the first day.

It was all intense, and we eventually ended up driving up to the top of this volcano/mountain that was supposed to have a killer view. Only to not be able to get out of the car because the wind, fog and rain were so thick that it was safer in the car. The tension in the car was so thick you could cut it with a knife. I was grumpy, my wife was grumpy, and the last thing we wanted to do was go to a Luau in the rain, but we paid for the tickets. So after a quick trip to the boat to get warm clothes and pants, we finally drove to Lahaina.

Did you know that the weather can be drastically different just a few miles/kilometres away because of the ocean, currents and shape of the island?; we sure didn’t. The closer we got to Lahaina, the more the sun came out, and as we entered the city, we saw one of those standard city welcome signs that read,

“Welcome – It’s always Sunny In Lahaina”

The sun seemed to break through the clouds at almost that exact moment, and the temperature jumped rapidly. I started to sweat, no-cook in my jeans (because it was cold and rainy). It was just simply gorgeous. It was so hot I had to buy a pair of shorts. At the shop, the lovely girl mentioned that not only had it been cooking hot that day, but that they had been in a drought for a few years and were desperate for rain. I mentioned that it had rained all day around the other parts of the island. She just shrugged and said something to the effect of “ya, I know, but it’s always sunny in Lahaina.”

We had planned this first day for months. Twyla and I researched options, planned our lunch stop and had dreamt about this day for a long time. But as soon as we saw the rain, it threw us into chaos. The fighting and arguing lasted almost the whole of that day. We both were ready just to go back to the boat more than once, call it in, and write it off.

The question is, why? Why did we let some rain derail our whole plan?

I think we can say the same thing in leadership sometimes.

  • Why do we let that one person drive the agenda?
  • Why does one decoration out of place wreck the party?
  • Why does one critique fester in our hearts?

We often put hours, weeks or even months of work into the things we do in leadership. So much energy goes into what we do, and then, at the last minute, something throws a wrench into the process. We freak out because we like to control and don’t like the unknown. I know I sure felt this way back in Hawaii. The heart of our need to control is a trust issue.

  • Do we trust the work we have put in?
  • Do we trust our team to do their jobs?
  • Do we trust that sometimes we can’t control the weather?

In our house, the rule is simple. If we have a plan and something comes up at the last minute, the weather changes, or for some reason, we don’t “feel it” anymore. Twyla and I look at each other and say, “it’s always sunny in Lahaina.” I have also started to apply this same principle to my leadership and work as a Pastor. There are all kinds of variables that I can’t control. But what I can control is my ability to trust that no matter what comes up, “it’s will always be sunny in Lahaina.”

Because here is the deal, we could have gone to Lahaina as planned, and it could have rained. But so what it rained? So much fun was lost because we didn’t trust our plans. In fact, the next day, it did rain, and we spent the day chasing the sun, eating tacos, getting lost and having fun. I ended up driving on a road that has become a memory I’ll never forget. All because we planned to be in Lahaina, and we were. We just rolled with what came and stuck to the plan regardless of the rain.

The leadership principle is that unforeseen and uncontrollable stuff will always come up. But will you trust the work that has gone into the moment, and when needed, can you flex your expectations and roll with the change. Because I promise you if you push against it, you will just be frustrated and a drama-filled leader.


First, I want you to think of a time when you planned an activity, launch or project that didn’t work out the way you wanted. Now hold that moment as you work through these questions.

  1. As you reflect, how much work and energy went into that activity, launch or project?
  2. How did it make you feel when things didn’t work out?
  3. Did you hold on to those feelings, or did you let them go? If you held on to them, why?
  4. In hindsight, how could you have responded to the change? Was there a better practice, response or process that you see now that you didn’t see then?


I want you to take some time to think of a motto you could use in your life, both personal and in leadership, that could help you remember “it’s always sunny in Lahaina.” Then share that motto with your group or someone you trust.

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