New York City Lawyer Would Rather Be a Travel Advisor

by Richard D’Ambrosio
New York City Lawyer Would Rather Be a Travel Advisor

Tammy O’Hara’s love for travel and curating perfect vacations is enticing her to trade in courtrooms for hotel rooms.

According to the U.S. Labor Department, the mean annual salary for a lawyer in the New York metropolitan area is about $172,000, equal to an average hourly rate of around $82. Comparatively, the mean annual salary for a travel agent is about $43,000, an hourly rate of about $21.

These numbers don’t deter Tammy O’Hara, a lawyer who lives in Brooklyn, New York. For the last three years she has been building her business, Million Miles Travel Agency, to pursue her passion for curating memorable vacations, and to one day perhaps make it her full-time vocation.

O’Hara doesn’t feel following a career in travel means forsaking the prospects of a solid income. She believes that, through an effective use of technology and targeted marketing, she can have the best of both worlds.

“This is the type of profession people get into because they love doing it,” said 35-year-old O’Hara. “They lose that love sometimes when they get overwhelmed. I am going to focus on making sure that I am working smarter, not harder, using the tools out there to help me.”

In her second year as an independent agent, O’Hara is on target to double her gross sales. A romance travel strategy she deployed in the first quarter was so successful, she had to increase her annual goals for that target market, she said.

“I’m shooting for $2 million plus in annual sales. You cannot leave that to fate. You have to have a plan, and a way to track it,” she said.

Working smarter, not harder
O’Hara is regularly on AppSumo, exploring and evaluating apps that can help her work smarter, and save time by automating manual tasks. For example, she is about to take on a new and more expensive customer relationship management (CRM) tool because it will eliminate a lot of administrative and communication tasks she performs manually now.

“Once you do that analysis, and realize the time you are saving can be deployed elsewhere, more profitably, it makes the decision easy for you,” she said.

Using Google Analytics and her CRM, O’Hara has determined that her ideal clients are women, 36-54 years old, with annual incomes over $80,000. “They are interested in food, want to go on retreats, and they are willing to pay a fair price to travel,” she said.

O’Hara plans and manages her own client marketing email blasts based on segmentation data she tracks through her CRM; and uses ConvertKit, an email marketing application, for building emails and tracking their performance.

“I have my clients segmented, and I have something like 50 different tags. This way, I know who among my subscribers clicks often on my emails, what they viewed, etc.,” she said. The interests they express determines what kind of content O’Hara’s agency emails them.

Meanwhile, her scheduling software is connected to her Google calendar; and O’Hara uses the web-based, to-do list app called Trello to keep track of administrative and other business tasks, as well as quarterly and current year goals.

“I’ve spent a lot of money to build my agency, but I feel it has really helped me clarify what my business is, and I have seen the results,” O’Hara said.

Catching the travel bug later in life
O’Hara didn’t travel much when she was young. Her parents had limited discretionary income, so travel was restricted mostly to see relatives in their home country, Jamaica.

When she took a few years off between undergrad and law school, O’Hara finally “got bit by the travel bug.” In her senior year of college, O’Hara was an avid Facebook user and would post photos from her trips – mostly cruises, the Caribbean, and Mexico.

Her Facebook friends would comment and ask questions: “Where are you going? You’re always going somewhere. Wow. That’s amazing. Can you help me?” she recalled recently.

Traveling stopped during law school, as O’Hara buckled down with her classes, work and preparing for the bar. She earned her law degree when she was 27. And when she got her first job as an assistant district attorney in Bronx County, she turned back to travel to relieve the stress.

Then, O’Hara was traveling to places like Costa Rica, Belize, even Europe for three weeks, with a focus on going “off the grid,” and finding hidden travel gems.

The first time she had an inkling she might book travel professionally was in 2014, right after she planned a friend’s vacation. “I told myself, ‘This is a lot of work. I can’t imagine people NOT doing this for money.’ But in New York City, you can find someone to pay for anything, from walking dogs to doing your laundry. I Googled ‘travel agents,’ and one of the first things that came up was scam warnings about multi-level marketing companies.”

O’Hara conducted more research, “because as a lawyer, I have to research everything, from laws to licensing, to insurance.” But O’Hara had student loans to pay off, so she put her travel agency dream aside.

At the end of 2015, O’Hara performed more research, including host agencies, and determined she could, at a minimum, make a part-time career out of her passion with the support of a host network.

On February 16, 2016, O’Hara joined a host agency. She filed as a sole proprietor shortly after, naming her agency “Million Miles to Rome.” (She eventually changed the name to “Million Miles Travel Agency.”)

Perfecting her game
Like most new agents, O’Hara took on every client she encountered, so she could perfect her booking skills. “Learning all of that was great, but I knew I wanted to work with clients who aren’t overly concerned about pricing, clients who will go above their budget if I could show them it is worth it,” she said.

But working within a host agency’s restrictions didn’t suit where she was headed. “You have to tailor your business to stay within their rules. So, when I wanted to target clients who would pay fees. My host wouldn’t let me. I also couldn’t really focus on my preferred suppliers for those clients.”

Participating in a travel agency Facebook group, O’Hara learned about CCRA and how their business model would let her be more independent. After more research, she jumped in.

Initially, it was “touch and go for a little bit,” O’Hara said. “You have to do a lot more for yourself. I had to sign up again with all of my suppliers to start fresh because I had a new agency number.”

“But now, I get to choose who my preferred suppliers will be, to match them with my ideal prospects,” she said.

Now, O’Hara has a menu of fees she presents to prospects upfront. “During my initial consult, I finish up by saying: ‘We’ve talked about what you want to do. Here is how the rest of the process goes. I charge a fee. I will send you the invoice. Once you send payment, I will have an itinerary to you in this amount of time.’”

O’Hara says her close rate when she gets a prospect on the phone is 80%, and that even with charging fees, her agency is growing faster than ever, to the point where she needed to bring on her second independent contractor recently.

‘I am not Expedia’
Today, Million Miles heavily books the Caribbean (especially Jamaica, the Dominican Republic, and Puerto Rico), Mexico, Central America (specifically Costa Rica, Belize, and Panama), Western Europe (Italy, Spain, Portugal, and England), and North and South Africa. Million Miles also serves destination wedding couples and honeymooners.

“I feel like I am a grown-up business now. I’ve been through it all. I’ve done my seller of travel applications. Done my E&O insurance. I’ve also transitioned from taking every client, to being selective,” she said.

She regularly turns down clients, especially those who are overly focused on price in their initial communications. “I explain to them: I am not Priceline. I am not Expedia. But what you get from me, you aren’t going to get from them either.”

Operating with two new ICs, O’Hara now has the option of passing price-conscious clients off to one of them. “It’s a way to keep the client in-house, but know that I am going to be more productive for the clients I need to work with,” she said.

O’Hara still works part-time as a lawyer, and she can’t let go of the legal profession just yet – though she considers herself “half way out” today.

Her plan is to be in a position to work solely on her travel business sometime in the next 5-10 years, but she plans on maintaining her license to practice law. She muses that she might even use her legal background to supplement her travel advisor income by offering legal services specifically for travel agents.

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