If you go on a vacation and take your clients with you (in the form of emails, texts, etc.) then that’s not really a vacation. A vacation for a Financial Advisor should be more than that.

The Dream Vacation for a Financial Advisor

I get it, customer service is one of the “levers” we can pull to be competitive and add value to our clients. I am not saying that you should ignore your clients when you are “off” but I am suggesting you put together a process and a team of people so that the answer doesn’t have to come from you. 

Then go on your dream vacation and feel great about it. 

Now that I have the business model that I do, I can honestly say I have never come back from a trip regretting it. My team will tell me if anything went wrong, how they handled it, and if I need to follow up in any way. Most times, emergencies aren’t REALLY emergencies and the world keeps spinning without you there. 

What Makes for a Great Vacation for a Financial Advisor?

Incredible vacations all include the same core elements. 

Planning the perfect Financial Advisor Vacation

Countless articles say that the most enjoyable part of the vacation happens before it even started! That tells me that you need to plan with a purpose. Visualize yourself on vacation, you don’t have to tell your spouse what you’re imagining. 🙂

Pick a date that’s a few months out and think about it for a few minutes every day. (I am not opposed to spontaneous vacations, for the record.)

There are two things to think about on vacation, and there’s one thing you should NOT think about. 

Budget For Your Vacation

Think about your budget. What do you want to spend?

I have a savings account set up that’s dedicated for vacation savings. Every week, I put two and a half percent of my take-home pay into this account. It’s a small percentage, so it doesn’t cut into my grocery bills (even though my wife insists on shopping at Whole Foods), but it adds up nicely over time. 

We go on a vacation once a quarter with a larger one planned for once a year. Each vacation is budgeted for a year ahead of time. 

This way, I know whether my vacation savings account is on track. When I get unexpected income, I put half of it towards fun stuff like vacations. The rest goes into my retirement account where it accrues interest so that I can keep doing fun stuff when I’m retired. 

The Vacation Mood

Think about what mood you want to be in on vacation. If you’re going to relax, then go somewhere relaxing. If you want to be inspired, go somewhere inspiring. 

Whatever you want to accomplish on this next vacation, write it down. Then, plan accordingly.

When my wife and I celebrate our anniversary together, that’s one mood. I plan that vacation very differently from the others. Once a year we do vacation for the kids, something like a Disney trip. When I plan that vacation, I make sure we spend a lot of time in Epcot because even though I love my kids, I like having fun too. 

There are other vacations when I need to just relax and rejuvenate from work projects or non-profit volunteering (saving the world is stressful sometimes, okay?!) For me, that’s when I go to a beach or getaway to my house in the Poconos. 

Do not think about other people

Alright, your jerk of a neighbor just got back from Tahiti with his mistress. 

Vacation is not about comparing yourself to him. Vacation is about experiencing life to its fullest. And Chad doesn’t know how to do that, so you shouldn’t be comparing yourself to him. 

So many people I know plan their vacation around what other people will think, and then they come home disappointed. 

Let’s be clear about something. Your next vacation is for you. Go where you want, do what you want, with whomever you want. Make it about you and don’t worry about what other people think. 

You have nothing to prove to anyone. If you want to take your wife/husband to the local bed and breakfast for an overnight, then do that. 

You have Mr. Retainer’s permission to not care what other people think. 

Vacation with the Right People

When you leave for vacation, remember to pack everything, particularly the people you want to be with. Think back to the mood you want to set. 

This year I did a weekend getaway with my father-in-law and some friends. We went to CigarFest for a few days. It was short but fun. We shared stories, laughs, and some good cigars. 

A month before, I went to the Bahamas with my wife and kids. It was totally different but just as memorable. We spend each day baking in the sun on the beach, laughing, and splashing in the waves. 

This year, I’m taking my wife on a fun getaway (if you tell her, I swear…) That vacation is going to be filled with romantic nights, good food, and even better wine. 

Last of all, once in a while, I’ll take a trip by myself. These trips are usually mixed with business, but not always. When I go alone it’s usually to be introspective. 

I’ll look at my dream journal, revisit where I was, take a look at where I am, and envision where I want to go. These trips are perfect for planning life in quiet solitude. 

Vacationing with the different people creates a different mood, so choose accordingly. 

Have the Right Vacation Attitude

When you go on vacation, think of a bar of soap (unless that brings back bad memories). If you try too hard to have fun on vacation, you won’t. 

Vacation should have just the right amount of adventurousness. Every vacation I go on, I force myself to try something new. Once it was sushi, another time it was skydiving. 

Face a fear. Try a new food. Talk to someone you wouldn’t normally say hi to. 

You’ll also need to be flexible. Rental cars get switched, plans get canceled, restaurants close. When you go on vacation, expect that things won’t go exactly as planned. Be at peace with it and greet every challenge or unexpected answer with a smile. 

End Strong

Studies prove that the best way to enjoy anything is to ensure the ending is pleasant. When you go on vacation, make sure your last activity before you leave is fun. 

Don’t end with a hangover, tempting as that may be. End with the best dinner, the most fun activity, some one-on-one time with your spouse or best friend.

Just make sure the ending doesn’t suck. 

If for some reason it does, then go back to setting your expectations and being flexible and focus on the good! (Hey, this is supposed to be a fun article. 

Unplug on Your Vacation

Unplugging is now a buzzword. However, there’s a very good reason for that. Most people think they’re connected, but in reality, they’re just distracted. Unplugging allows you to recharge, to relax, and to enjoy life. 

I say it’s time for financial advisors to enjoy life a little more. It’s time for a Vacation for a Financial Advisor, and that means you.

Rules for Vacation

Create rules for your next vacation. Think about the things that annoy you when you go away. Either readjust the way you think about those things or set a parameter to not allow those things to go on vacation with you. 

Rule 1. No checking email while on vacation.

Rule 2. No checking business texts while on vacation.

Rule 3. No answering work calls while on vacation. 

Rule 4. Any time spent thinking about work on vacation will be limited to Strategy and Big Picture Vision. 

Rule 5. Vacation is for Fun.

Rule 6. I follow all the vacation rules. 

Prepare for Vacation

Let your team know you are leaving. If you have clients you talk to on a weekly or regular basis, let them know, too. 

If either your staff or your clients resent you for taking time off, be prepared to part ways with them. You don’t need that kind of negativity in your life. 

Trust Your Team

The biggest problem I see with financial advisors and business owners is that they worry too damn much. 

When you leave for vacation, trust that your team will look out for you. If they don’t, then you didn’t hire the right people. Adjust accordingly. You may just have a classic example of the wrong people in the wrong seats. 

Trust Your Processes

If your team tried but didn’t come through, there could be a couple of issues. The first is that you likely didn’t leave them with the right processes for success. The second we already addressed above. 

Take a Few Days When You Get Back

When you get back from vacation, spend an extra day or two at home with the day off. This will help you to adjust to being home. 

It will also give you some time to revisit the memories you just made. 

Lastly, and most importantly, it gets your team used to operate without you. This is what you want so that you can scale your advisory. 

Top Locations for Vacations for Financial Advisors

The Classic Beach Trip

Most vacations for financial advisors consist of trips to the Jersey Shore or Laguna. There’s a good reason for this. For millennia, people vacation at the shore. 

The ocean is calming, relaxing, rejuvenating. 

The beach is my go-to vacation when I am feeling tired or wiped out. 

Vegas or the Nearest Casino

Some financial advisors work in the industry because they’re addicted to money. If that’s you, then the casino is the place to be. 


The European vacation is a classic. Big Ben, Parliament. 

There’s so much to see in Europe, I suggest you go to a travel blog and let them guide you through the process. I am hardly qualified. 

The Staycation

There are probably a lot of great places within a short driving distance of your practice or your home. 

I find the local restaurants and hotels to have some of the hidden treasures of fun. Hop on TripAdvisor and look for the best-rated places in your area. Do a short weekend getaway and have fun!


The last style I can think of is an exotic vacation. These are the crazy vacation where people go away for a month. Like Chad in Tahiti. 

My top spots include Fiji, Nepal, and Newark. 

My Challenge to You: Plan Your Next Vacation

Email me where you are going and when you’re leaving. Plan it today for within the next year. I don’t care if it’s a weekend road trip to a winery with your wife. The Vacation for a Financial Advisor starts now.

Do it. 

Reward yourself for your hard work and implement some of our advice to make the next vacation one that’s unplugged. 

If you send that in, you’ll get a free 15-minute coaching call with me, and you’ll be entered to win a 3-month coaching package at no cost to you. Just send a note to concierge@retainerbasedacademy.com and we’ll make it happen. 

Make sure to check our Youtube channel!

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