After decades of building successful tour companies, many travel business owners are asking themselves the same question: “Now what?”

It’s asked against the backdrop of a changing world and an evolving travel industry. Boomers in the group travel market are being joined by Gen Z and even Gen Alpha travelers. Technology is reshaping every aspect of owning a business, from marketing to daily operations. And finding new leadership is an age-old challenge that confronts every generation and every industry.

But whether you’re a legacy tour operator looking to close an illustrious career or still steadfastly steering your business into a bright future, there are some common problems many longtime operators in the industry are facing. Even if you’re decades away from retirement, it’s never too early to start considering them.

Here are five problems currently facing legacy tour operators — from succession challenges to business development — and some potential solutions worth investing in.

Problem 1: Legacy tour operators don’t know how to attract new customers.

Sustaining a travel business that spans decades depends on the business’s ability to attract new customers. “New” might simply mean new faces within the same target audience, or it could mean that the audience needs to shift to accommodate a new group of people. Both will inevitably be true, especially when it comes to welcoming new generations of travelers into your travel tribe. As Gen Z ages into the world of leisure travel, they’re occupying an increasing share of the market and shaping travel trends for decades to come. Not catering to multiple generations could mean that you’re giving your business an end date.

Solution: Hire and empower younger people.

It can be difficult to trust someone without years of expertise under their belt, but young professionals have the advantage of knowing what younger customers want. That’s why bringing in young professionals can have a profoundly positive effect on your business. But it’s not enough to simply hire younger people; you also have to empower them to share their knowledge and implement their ideas. Giving them some leeway to make decisions and voice their opinions might not only build their confidence, it might also give your business a boost.

Solution: Invest in outside expertise.

Tour operators are used to wearing a lot of hats, but it’s okay if they can’t wear every single one. There are plenty of people you can turn to for assistance with attracting younger clients, from outside marketing agencies to individual contractors. This expertise will look different to everyone. It may look like hiring someone to build and manage a strong digital marketing campaign or bringing in younger guides that can better connect with Gen Z groups. Either way, don’t be afraid to ask for expert help.

Problem 2: Legacy tour operators are struggling with the tech tools they need for digital marketing.

Personal referrals are a powerful tool for attracting customers, but in 2026 and beyond, a travel business without a digital footprint can only sustain itself for so long. Digital marketing is consistently growing in importance, especially if you’re trying to appeal to younger travelers. But many legacy tour operators may feel out of their depth when it comes to developing a website, maintaining a social media presence and targeting customers with email marketing campaigns.

Solution: Be self-aware about your strengths and weaknesses.

In the 1940s, psychologist Raymond Cattell introduced the idea of fluid and crystalized intelligence. Fluid intelligence, which peaks early in life, is the ability to solve novel reasoning problems and adapt to new situations, while crystalized intelligence, which peaks later in life, is one’s knowledge, skill and judgment accumulated through experience. Psychology has a lot to teach us about ourselves, including when it’s easier for us to learn and embrace a new skill and when it’s best to delegate learning a new skill to someone else. Knowing yourself can help you decide if it’s worth extra training and hassle to master new technology, or if you should entrust other members of your team. The answer to that question could save you time, effort and money.

Solution: Build infrastructure before you think you need it.

Building digital assets for your brand is not something you can do overnight. It takes time, investment and a well-planned strategy to create components that align and do their job well. For example, a social media page can only do so much if you don’t also have a website for potential customers to further investigate your products. If you’re thinking that building an online presence for your business is something you can get by without, think again. You can pretty much guarantee that the next owner of your business will to have to spend a hefty sum first thing when they acquire your business to make up for the digital deficit. Start building online infrastructure before you think you need it. It might end up being less work and less expense for your successor to shore up your materials than to create new ones.

Problem 3: Legacy tour operators lack an “heir apparent.”

Many tour operators feel the best person to inherit their business when they retire is one of their children or a younger relative. But not everyone has that “heir apparent” who is an obvious choice, which can sometimes leave legacy operators scratching their heads about succession. Other problems can arise if they have too many “heirs” striving to inherit the business. Here are some solutions for tour operators looking to create a strong succession plan.

Solution: Look outside the box to find your kindred spirit.

Your successor doesn’t have to be limited to family; sometimes the best person to buy your business from you will be found in an unusual place. Consider other people in the travel industry with whom you have a strong connection, whether they’re on the supplier side or the operator side of things. If there’s someone you always find yourself getting along with, or if you’ve noticed someone taking an interest in your business, they might be worth asking. And while it may feel like sacrilege, sometimes the right person to buy your business may even be a competitor. If you have a respectful relationship with someone who competes with you in your corner of the market, they might be interested in buying your travel business and inheriting your customer base.

Solution: Hire a business broker.

If no one stands out as a clear choice (or you’d rather avoid mixing business and family), but you’re interested in your business continuing after your retirement, a business broker might be the best solution. They can find the right buyer for your travel company, and that buyer may very well be the answer to some of your company’s biggest problems. This isn’t necessarily an easy solution, as it’s very difficult for business owners to let go of the legacy their companies have created, but it can be an effective tool to help them profit from their lifelong efforts and even restore their company back to health.

Problem 4: Legacy tour operators are keeping everything in their heads.

Many legacy tour operators have decades of institutional knowledge steering them toward success. They rely on their current relationships with vendors and destinations, their own knowledge of their customers, and their own tools for contract negotiation and day-to-day operating procedures. But this presents a problem if they want the business to continue after they retire: If everything lives in their heads, their businesses can’t function without them at the center. They have effectively become the business.

Solution: Get the business out of your head.

To make sure your company can outlast you, you’ll need to get information out of your head and onto the page — or more accurately, into the computer. If you don’t already have digital records of clients and their preferences, vendors and suppliers, or past trip itineraries, that might be the first order of business. You should essentially be creating documents that could be used for onboarding someone to take your place so that you have a written record of how you do business. If this seems a rather monumental task, you can use AI to assist by asking it to build sample checklists, training documents and standard operating procedures. You can tweak the output as many times as you need to get it right, and it’s easier than starting from scratch.

Solution: Cross-train your staff.

If you’re not a one-man show, your existing staff likely has at least a partial picture of how the business runs. But they’ll need a full picture to be able to keep things going after you retire or sell. Make sure they see what all sides of operations look like. In the years leading up to your retirement or selling, you should also be gradually transferring your most important relationships that maintain the business. You can do this by bringing your staff to networking events and travel conferences, copying them on emails, and taking them on trips to ensure they have a full picture of what you do and who you do business with, from DMO representatives to your guides or receptive operators. It also gives them the chance to develop their own strong relationships with key players in the industry.