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How I Closed a Five-Figure Deal for $100 in Dubai

This blog post was first published on Upside as part of a promotional partnership. Use code COWORKAHOLIC to get $100 in Gift Cards when you book your first trip!

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Business Travel Takes A Toll In A Variety Of Ways

Being a business traveler can take a toll on folks in a variety of ways. For some it’s time spent away from loved ones; others bemoan the effects on health and overall wellness. If you’re traveling for a company, however, it’s rare that a toll be financial. For employees with either a company issued card or reliable 30-day reimbursement window of payment, chances are you’re not losing sleep over cash flow, making payroll, or lowering business development costs.

Well…as a freelance consultant business traveler (or Coworkaholic), sometimes I don’t have the luxury of those options. And, I’m certainly fronting the bill when reviewing coworking spaces, attending networking conferences, or producing events like coworking safaris. Most of my work can be virtual, but when the project is big enough – like putting a coworking space in a 650 room hotel – you gotta close the deal in person.

The “Points & Miles Game”

That’s why I love to play the “points and miles game” as my mom puts it. By maximizing how I earn on paid client travel, in addition to a bunch of other crazy, fun ways, I can travel for almost free. Without worrying about how much I had to spend, I find that it’s way easier to close the deal or network with charm without the risk of losing my shirt looming over my head.

If I’m not using Upside to get the lowest overall price on a trip like this, I’m hustlin’ all my points and miles to cover the cost. The best example of that? A trip in May 2017, when I took a speaking gig in Barcelona and tacked on a stop in Dubai to close a deal for little to no extra cash. The challenge was how to get from Chicago to Dubai to Barcelona back to Chicago on a speaking engagement flight stipend of only $1,000.

First Up? Airfare…

First priority was finding cheapest airfare that worked with the prospect’s schedule. It just so happened that Swiss was running really affordable flights between DC and Dubai, with a connection in Zurich, especially with longer than usual connections, like enough time to perhaps go to Barcelona.

Lucky for me, I have clients in DC, so my round trip ORD-IAD ticket was covered. I booked the rest through Swiss, earning me MileagePlus miles, while also enjoying Star Alliance Gold benefits like lounge access, preferred seating (sometimes) and priority boarding. I booked IAD-DXB round trip (with a “long” connection in ZHR) then ZHR-BCN round trip (codeshare flight on TAP).

Second? Hotel, Food, Transport & Client Entertainment…

Next up was tackling the costs of a hotel and client entertainment/meeting costs, with a little sightseeing while catching up with a college friend. Thanks to the (since ended) SPG/Uber partnership – RIP – I had racked up a TON of SPG points thanks to a (too) generous earning ratio and bonus for when ubering while staying at an SPG property. Those transferred quite nicely at the 3x ration to Marriott Rewards (mind you it’s all different now post Marriott/SPG merger….sorry!).


Thanks to my United Gold Status, at the time, I got a Marriott Gold match. That allowed me to book the cheapest award rate possible at the JW Marriott Marquis Hotel Dubai and was welcomed warmly with an upgraded room and access to the lounge, which is still the best Marriott lounge I’ve seen yet.

Sure the upgraded room was nice, but lounge access made the world of a difference. This meant that I didn’t spend anything for food, except for one breakfast with my friend under the Burj Khalifa and a coffee at The Dubai Mall. I was also able to host my future client for our meeting and post-business drinks/get to know you time that one must partake in to get a signed contract.

Taxis are also quite cheap, (and the Uber/SPG partnership had already ended) so all in this deal cost me 40,000 Marriott points, $20 in taxes and around $100 for taxi, tips, breakfast and postcards. Then, it was off to Barcelona for the retreat!

Not too bad of a ROI when you can score a mid five-figure contract…from a different trip that was already paying your airfare, right?

4 Tips For Maximizing Your Travel ROI

1. Check your work (and personal) calendar to see if the timing works to add an extra day or two to your travels. If the stars and flights align, you can fulfill your responsibilities for one client–while making time to see another who may very well live in another city or country. If you’ve already trekked halfway across the world, it’s a lot easier and cheaper to add another stop to your itinerary as opposed to having to plan a separate trip.

2. Resist temptation to burn those points and miles as soon as you earn them. You never know when you’ll need a last minute flight or hotel room. Make sure to always have enough points and miles to cover a round trip flight and at least a one night stay for an emergency. You never know when you might need to take a meeting in person, last minute. Or perhaps your business partner books a Basic Economy ticket and becomes violently ill when departing an industry event, forcing them to miss their flight home. 7,500 points for an extra hotel night and 10,000 miles for a one way ticket is far less painful than paying what would have cost more than $600 (not counting that lost Basic Economy fare).

3. Take advantage of status matches to get perks you might not otherwise be eligible for. Airlines, hotels and rental car companies all have preferred partners and those come with reciprocal benefits. While we’re all still getting accustomed to a post SPG/Marriott merger world, there’s no way I could have hit Platinum in either program if it hadn’t been for my status on United. Earning Gold status with Marriott and SPG just for being Gold on United? Not bad. Getting Platinum because I only needed 25 stays after becoming Gold rather than working up to it the hard way with 75 stays? Even better!

4. Spend the extra time to do the math because a slight change in habit can pay off in spades. I spent a ton of money on Uber when it made sense to do so. When their partnership with SPG ended, I re-evaluated my spending on ground transportation. Sure it took about an hour or so of number crunching, but I realized that more than half of the time, renting a car would not only be actually cheaper, but I’ve been able to rack up over 100,000 miles while also driving some pretty sweet rides.

Do you travel for freelance work? Share your greatest business travel wins in the comments below!

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