Managing Money Stefanie O’Connell on Living the (Affordable) Jet-Set Life

by Roger Kamholz September 04, 2018

Photo courtesy of Stefanie O’Connell

Early in her career Stefanie O’Connell was giving her all as an aspiring actress but still found herself treading water financially.

When she faced a sudden (and sizable) dental bill she simply couldn’t afford to pay, she had a budgeting breakthrough moment. It jolted her into a realization: She had to better educate and empower herself when it came to money, or else the cycle of struggle was never going to change.

Fast forward to today, and O’Connell is educating thousands of fellow millennials on being smarter with money — especially when it’s scarce —through her writing, TV appearances and more. The author of The Broke and Beautiful Life advises on how to manage a tight budget, particularly when it comes to affordable travel. Life and Money by Citi caught up with O’Connell recently to tap into her thoughts on getting away for less — while making the most of being there.

Where have you been lately that has inspired you?

I went to Barcelona in March, and I took a cruise from Barcelona to the Canary Islands and Morocco. I’ve been thinking about getting back to Spain ever since and exploring the rest of the country. I love the culture, I love the cuisine and it’s a beautiful landscape.

I particularly liked the city of Barcelona because it has that cosmopolitan vibe, but it has really old culture and classic, incredibly unique architecture. Little pockets of inspiration are around every corner.

How do you immerse yourself in a destination when you are abroad? 

The first thing: consider your housing. If you are staying in a hotel, it’s probably geared toward tourism. There is nothing wrong with tourism, but if you are trying to have an immersive travel experience, you are probably going to be looking for more of an apartment in a residential neighborhood rather than a tourist neighborhood. If you stay at a hotel in Times Square you are not going to have a really local experience, compared to if you stay at, let’s say, a short-term rental where I live, in Harlem.  

Do some research online for “hipster neighborhoods” — it sounds silly, but those tend to be really cool centers of various cities, and I’ve used that strategy a lot to find things that are maybe a little outside of that mainstream tourist area, and to find the cultural centers and local hangouts.

Coffee shops are a great center for local experiences. You will by nature connect with people who are local there. You can speak to those people about what they would recommend. When you are traveling, so many amazing things can happen when you connect with people.

It’s a little less structured, but when you have the time to immerse yourself, you can have these unique experiences that you might not get from a very strict itinerary.

How else do you approach your trip planning?

Think about what kind of experience you want to have. How much time do you have available? Does that give you flexibility or do you need to be a little bit more regimented? Depending on your answers, you can start to think about the kind of experience you want. And then you can start doing research based on those experiences.

Like I said, for a more immersive experience, I would look into local neighborhoods. I would look into local activities. Search keywords like “off the beaten path” and “local hotspots” — those things can all turn up really great results.

Travel guides are a great starting point, but check out sites where you can actually see reviews, because you’ll find a lot of hidden gems in reviews. You’ll find things like, if you go on Tuesday to this museum, there are free hours between 3 and 6 p.m.

Search keywords like “off the beaten path” and “local hotspots” – those things can all turn up really great results.
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What piece of travel-planning wisdom has been a game-changer for you?

When I’m looking for recommendations for my travels, I’ll post on social media. People who have been to those areas or know people who have been to those areas will connect you with somebody there. That person then becomes a major resource for you.

I’ve said things like. “I am thinking about traveling to Colombia.” All of sudden I got like three messages from people connecting me to their friends in Colombia, who then took me around, who let me stay with them and who recommended things to do. So, I got both the insider’s guide and a whole bunch of free stuff, just because I was connecting through my network.

We tend to overlook how far our network expands, but even one degree of separation is a huge swath of people all over the world. If you can leverage that, you’re going to be doing really well.

How do you look to make a work trip in part about yourself, so it’s not all about business?

Once I have fulfilled my work obligations, I will either use my miles, or pay for it if I don’t have the miles, to take a little side trip. For example, about 10 years ago, I was in Manila for about two months. I had this four-day window between engagements, and I was like, ‘Oh, let me see what else there is to do while I’m here.’ I looked up flights from Manila to Boracay — an island that’s part of the Philippines — and they were so cheap! And it was one of the most beautiful destinations I’ve ever been to. It was amazing because to go to Boracay from New York would be completely cost prohibitive. But because I was already halfway across the world, the vacation was, all-in, maybe like $400 for accommodations, flights and food.

I am always trying to find those opportunities when I have a moment to say: Okay, how can I really maximize this and leverage the opportunity I have already been given through work to do something that is personally rewarding — even if I’m in a city?

Last week I was in Seattle for about 24 hours for work — and that’s a long flight because I live in New York City. But once I got there, I went for a run. Then I did my business meeting and then I flew back. That simple hour of my time to go take care of myself physically, but in that different space, was so rewarding. It allowed me to see and experience that city, even if just for a moment, just maximizing those little windows of time, whether it’s one hour or it’s a week.

What are some things you do to make yourself a better traveler? During or after a trip, do you keep a journal to document and reflect on the things you’ve done?

I am a money tracker; in my day-to-day life I track every dollar I spend. That doesn’t change when I travel. I like to charge as much of my spending as possible on my credit card, because that gives me the full written statement when I get home. But that record also serves as my guide in a debrief kind of way. Where did I go right and maybe where did I go wrong? It also helps me plan for the future. How realistic was the budget I set? Can I afford to splurge more? Do I need to think of more cost saving strategies? My spending record is really valuable.

Oddly enough, my spending record can be a little bit nostalgic for me, too. So, I have all these spreadsheets…I’m such a geek! I have spreadsheets for the last five to seven years of my spending. I was looking something up from a couple years back and I saw all these expenses from Egypt, where I visited two years ago. I just had this total nostalgic moment of being transported back to the pyramids. I even was looking at my spending and re-living the memories through it. So, it was an oddly pleasant experience to have that record to go back to. And of course, along with my spending record I have all of my photos and all of my videos, and together that helps me paint a very holistic picture of where I was, what I was doing on any given day.

How realistic was the budget I set? Can I afford to splurge more? Do I need to think of more cost saving strategies?
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6 Affordable Travel Tips from Stefanie O’Connell

According to Citi research, 38% of consumers say the most stressful part of their travel planning is the budgeting. So if you can reduce the cost, then you can reduce the stress, right? Here are six of O’Connell’s smart strategies for managing travel expenses.

1. Pre-pay as many expenses as possible.

“It’s much easier to stay grounded in your budget when you’re still in your home and still planning your trip. So that’s when I pay for bigger items like the hotels, flights and any activities. Then I am not at risk of getting swept up in the moment to, like, upgrade to the presidential suite because I’m in Paris and who cares.”

2. Plan trips around friends and family.

“I ask myself, ‘Who do I know who lives in and around the cities that I want to go visit in the United States and beyond?’ Connecting with those people, seeing if they are available to play host and will serve as a local guide, can help to break up some costs.”

3. Opt for public transit.

“That can also contribute to a local experience. If you are taking the Metro or the Tube, you are going to have a much more local experience than if you are constantly sitting by yourself in a taxi.”

Who do I know who lives in and around the cities that I want to go visit?
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4. Travel during the off season.

Coming up on August, I’m eyeing a trip down to the Caribbean. I’m going to check the weather before I go. But by going during the wet season, I can cash in on those summer deals and summer savings — because it’s not high season.”

5. ‘Splurge’ on lunch.

“I know that is extremely specific, but what I mean by that is, a lot of really nice restaurants that might be really expensive for dinner will have the same kind of menu for a much lower price if you do that around lunch time. I’m kind of a foodie which is why my focus immediately goes to food. If you re-think your timing and make lunch the main meal of your day, then you can really save a lot of money and enjoy your splurge at a much lower value by just adjusting your timeline for how you are indulging in things.”

6. Earn miles while you travel, and at home.

“I’m a big fan of my rewards. I travel a lot both personally and for business, so I rack up my miles through travel. Plus, that way I don’t have to worry about converting cash all the time. But I also rack them up through my everyday spending, because I use my travel credit card to pay for pretty much everything that I can. That way I can really maximize and build up miles for that next trip.”

Nice restaurants that might be really expensive for dinner will have the same kind of menu for a much lower price if you do that around lunch time.
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Roger Kamholz creates content for Citi’s Global Consumer Bank. He has written about dining and travel for more than 10 years, and also has a soft spot for Barcelona.



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