Gosh… I Really Need to Get On a Plane

A man is looking out from a plane window

The first time you went to a restaurant without your parents and paid with your own cash, the first time you took your friends on a ride with your (parents) car, the time you moved out from your parents house to live on your own, your first meaningful job – all of those are defining moments in your journey to become an adult.

I remember all of these moments quite clearly even though decades have passed since. In each of these moments I felt both scared and excited. I also felt empowered and free. It felt awesome!

The first time I was sent to meet customers abroad by my employer I felt exactly the same. It was a decade after I made it through all the aforementioned milestones, and I already was a ‘responsible adult’ by any standard – and yet – funny enough – I was surrounded with the same level of excitement and I felt like ‘I’m doing it like grown-ups do’. 

As part of preparing for my first business trip I asked my colleagues tons of questions, trying to prepare for every scenario. They were seasoned travelers so they found my excitement quite amusing. Most of them told me:

“Dude… after a trip or two you’re going to hate it. The logistics are a big headache, filling the expenses report is terrible and the pile of work that we’ll be waiting for you when you’re back is gonna be huge. Trust us – don’t go on business trips unless you have to”.

Luckily I didn’t listen to them. I truly believe that most business trips can be fun (unless you are spending more time abroad than in your office) and in this post I’ll share some of my personal stories and provide you with tips on how to make the most of it. Even if you’ve been to several trips already – I recommend hearing me out, because you might find a new way to extract a bit more ‘fun’ out of your trips.


Wait – I thought Covid killed the concept of business trips

Well… it did – for two and a half years. But good news – business trips are back!

Yes… the business world is probably not going back to what it used to be in that sense. Companies have learned that you replace many of these trips with Zoom calls, and hence business trips are not fashionable as before (especially these days as businesses are trying to conserve expenses). However, at the end of the day (and any industry veteran can tell you that) – there is nothing like a face-2-face meeting with a person for building true, long-lasting relationships.


My first business trip

Instead of just listing tips, I thought of sharing my personal story of my first business trip (don’t worry – the tips will come afterwards.. :-)).

I’m taking you back to 2006. I was an R&D manager back then, working for a corporation serving enterprise customers. My boss told me that the sales team needs technical support with two important customers and I am going to join them for these two meetings.

“Ok…” – I said. I was excited and worried at the same time.

“Great.” – said my manager and continued – “Here is the thing, though – one of them is in Atlanta and the second is in a small town in Michigan. You are meeting the first on Wednesday and the second on Monday afterwards.”

“Ok… how do I get from Atlanta to Michigan?” I asked.

“A flight, of course” – he answered.

“And what am I gonna do between the meetings?”

“I don’t know. We’ll set you up with a nice hotel. Don’t worry”.


It was my first business trip, and I was afraid to ask too many questions because I didn’t want to look too dumb. However, it kept bothering me – what exactly am I gonna do all these days in between? Recall – there was no Netflix and Youtube was just warming up. And besides – how much time can you spend online anyway? There is a real world outside that I have never seen. Why can’t I get a taste of it? If I’m gonna cross the ocean and spend a week in the US – I want to do more than just running 3 hours of meetings and passing time in hotels.


I checked the distance between the two places. It was a bit more than 900 miles. I started doing some math. I got 4.5 days to cross this distance. Why not do it by car and experience the US the old-fashioned way?

The more I thought about it – the more my level of excitement was rising, together with another voice in my head which told me I’m crazy, and better play it safe. It was my first business trip, after all.

Eventually my excitement won. I decided to go for it.

I talked to my manager and I told him I want to rent a car instead. I proved to him that it’s gonna cost less to the company overall. He thought for a few moments and then said:

“Fine, you are an adult. However, if you don’t make it to the second meeting on time – there are gonna be consequences”.

I nodded and went immediately to the administrative officer in our office. “Cancel the flight ticket. Get me a car and a GPS (there was no Waze or Google Maps back then)”.

And so I did it –

I drove all the way from Atlanta to Michigan, and I also made a rule – avoid any highways unless I see that I don’t make it to my daily destination on time. Each day I booked the hotel for the next day and that was my daily goal.

I experienced the mid-US in a quick, but satisfying way. Did you know, for example, that Kentucky & Tennessee are very beautiful and green?

Did you know that some of the diners on these side roads are serving amazing blueberry pancakes? 

Luckily, phones didn’t have cameras back then, or otherwise I probably wouldn’t make it in time…


Looking back – it was one of the most fun experiences I had.

And now, let’s go back and evaluate the ‘safe’ alternative for a second – if I would have taken this venue I would be meeting the first customer, and then spending one or two days in Atlanta (which is a nice city, I have nothing bad to say about it) and then taking a flight and spending the other days in a small town in Michigan, waiting for my 90 minutes meeting with my other customer and immediately afterwards start my journey back home.

Which option sounds more fun to you?

Yeah… I took a risk. But it was a calculated one. 

Remember – this blog is about adopting an entrepreneur mindset when doing your job. Thinking out of the box and taking calculated risks are part of it. In this case I was able to execute a solution in a way that was a win-win for both my company and I.

My company spent less money for the same results and I had some fun doing my work.


Of course, most of the business trips don’t span over such big distances, and this was a unique opportunity. Nevertheless, most business trips do offer opportunities for personal enjoyment other than just doing your work. You just need to look for them.

And with that in mind go ahead and read these tips for making the most of your business trip:

My tips

Be professional

Yeah… sorry to get back down to earth for a second – but before getting to the fun part – let’s not forget the context. When going on a business trip – you are assigned with some business goals. Most likely it’s around meeting customers or meeting colleagues from an offshore office.

Stay focused on the target and be professional. Do whatever preparations are needed to maximize the chance of meeting these goals.

That includes:

  • Setting up your calendar and schedule
  • Booking a hotel which is less than 1 mile away from your meeting place (try not to rely on public transportation).
  • Learn about the dressing code and fill your suitcase with proper clothes
  • Master the ‘why’ of the business trip. Why are you going on this business trip and what would you consider as a success?
  • Double check your itinerary and finalize your travel arrangements. Make sure you’re not going to be late to any of these meetings/gatherings. 
  • Any other specific arrangements which are unique to this business trip and will increase the chance of success


Remember, failing to meet these business goals will make your managers think twice before sending you again on a business trip. So meeting the business goals of the trip must always be your first priority.

Join forces with someone you like

One of the main reasons some people are trying to avoid business trips is that they don’t like the loneliness that accompanies such business trips. Loneliness is indeed a big downer if you don’t like to be alone (personally, I embrace being on my own from time to time – but it’s not for everyone). 

So if doing this trip on your own is something that can potentially ruin your experience – try to either invite a colleague to join you, or check if by simply changing the time of your travel you can join one or more of your colleagues.

Of course – it must make business sense. For example – don’t join a colleague on a flight to a different destination and then make excuses of why it’s the right thing to do. Recall – be professional before anything.


If you can’t join forces with anyone from your workplace, try to see if you can hang out after hours with one of your customers. Does it make sense to invite them for a beer?

If the relationship is not too formal – then it might make total sense. I’ve been with customers who were more than happy to take me around town and show me some unique places that I’d have never found on my own. It was really awesome.

If done right – this is one of these things that create great long term relationships. 

In order to avoid out-of-pocket expenses, try to check beforehand what is your company policy around that and how ‘generous’ you can be with your customers. If possible – agree on that in advance with your manager.

But if, for some reason, your company is unwilling to pay you for after hours activities with the customers then it might be very well worth it to do it out of your own pocket. I’m not suggesting buying them a 200$ dinner with your own money, but spending 50$ on a great evening is not too bad.

Learn about your destination

Most places on earth offer sites worth visiting. It could be a great restaurant. It could be a short hike on the outskirts. It could be a unique landmark. It could be a museum. It could be a great place for shopping. It could be a park. Most probably – it’s a mixture of the above.

Unless your customer resides in a real dump – there is probably something worth seeing or visiting.


Do your homework and understand what you want to see and how it’s gonna fit your schedule. 

I used to wake up early and visit a site or two before the first meeting. If you are not a morning person, or the site is not open at these hours – then you can do it after the last meeting of the day.

If your schedule is very tight and your days are completely full, see if you can take the flight back on the next afternoon rather than right after the last meeting.

Most workplaces won’t ask you to take a day off in such a constellation, so you’ll be able to do a ‘quickie for the soul’ right before heading to the airport.

Consider extending the business trip to a short vacation

You flew into a different country, with a different culture. Can you tell when is the next time that you’ll be here again? 

If you are uncertain when or if you’re going to be here again anytime soon – consider extending your trip with a short vacation.

Listen to this – I was once sent to Tokyo to meet some customers. I always wanted to visit Japan, but it certainly wasn’t on the top of my bucket list. But hey – an opportunity showed itself and I’m coming to Tokyo!

“Only god knows if I’m gonna be here again anytime in the near future.” I told myself. So of course I extended my stay and walked the whole city back & forth.

Be highly involved with the travel arrangements

Many workplaces will try to save you time and arrange the trip for you. The intention is good, but the appliance of that is usually not great.

When I handed it over to others to arrange the trip for me, I got a shitty spot on the plane, I got crappy hotels or locations that simply didn’t make any sense.

You need to understand that the person who is responsible for taking care of your travel arrangements is also doing so for many other people in your company and very often they just want to get this task off their table. The result… as I noted… is mediocre at best.

Release this person from this responsibility. Tell them you highly appreciate their time, but since you are picky you prefer to do it yourself. Ask for the budget constraints and the company policies and work within that.

Only book highly rated hotels and with many reviews. As noted above – I recommend the hotel to be less than 1 mile from your destination so you can walk there. In many countries the public transportation is simply unreliable or just inconvenient – so why not do some exercise and walk to your destination?

Stop on the way. Eat a local breakfast. Absorb the air and the atmosphere. Watch the people.

You can’t do that if you’re grabbing a cab or a subway, right?

If you have been to this destination many times already (for example – I’ve been many times to NYC), and you’re confident that you can time the public transportation properly – then fine. Find an accommodation a bit further in a place which is a bit more exotic and that you have never been in before.

For example – in 2014 I was doing fundraising in NYC. I stayed with friends in Harlem. I went jogging in Central Park in the afternoon. It was very nice and different from my usual NY experience.


As for flights – do what you can to improve your flight experience. Personally, the flights are what I dislike the most about business travels. Therefore, I invest a bit of time optimizing my experience in any way I can.

For example – sometimes your workplace will be willing to pay for extra leg room on the international flights. Embrace it. It will make your flight experience much more convenient.

Needless to say – choose the seats yourself and based on your personal preferences (window or aisle). Nobody wants to be placed in the middle seat, but if you hand over your travel arrangements to someone else – there is a good chance this is exactly where you’ll end up…

Also – choose carefully the airline company. You may have a personal preference already, but if not – choose based on reviews and time of departure. 

Don’t forget to assign your frequent flier number if you have one.

If you are going to the US and you have a connecting flight (and you are not a US citizen) – don’t underestimate the time you’ll spend in the line for the immegration officer. I once missed a flight because I was stalled for too much time (more than 1.5 hours) in the immegration waiting lane. Plan for at least a two hours gap from the time you land in the US and until the departure of the connecting flight.

In short – take control over whatever your company allows you to and within the budget constraints.

And by the way – if the company’s budget is too limiting for the experience you’re after – then consider paying for some upgrades with your own money if the gap is not too big. It will result in a much better experience.


Expenses report

In many companies – filling the expenses report is quite a nightmare. Today there are advanced systems that aim to make it easier, but it’s uncertain whether your company will use such one.

So first – as part of planning your trip – understand in advance what you need to do in order to be reimbursed properly and as fast as possible. Different companies have different policies and systems to enforce these policies.

If your company requires you to keep all original invoices then it can be quite a pain, but with a bit of discipline it’s not that bad. Photograph each invoice after receiving it, just in case you’ll lose it.

I would recommend managing a spreadsheet and at the end of each day – just fill up the expenses for this day. It will take you 5 minutes, and will save you tons of time for when you’re back (when you won’t remember anything).

If you are bored on the flight back – you can start working on the expense report. Worst case – it will bore you so much that you might be able to finally get some sleep on the flight. 🙂

But anyway – with a little discipline – you can greatly minimize the headache involved with filling up this report.


Handling the work that piled up on your desk while you were gone

Well… you know what they say – the best way to tackle a problem is to avoid it altogether.

If you don’t want to have a huge backlog of tasks that you’ll need to work on when you are back then you need to make sure it’s not piled up to begin with. You can try to achieve that by setting proper expectations with your team in the following manner:

  1. Delegate, delegate, delegate. One of your team members always wanted to be a team leader? Great! This is their time to shine. Ask them to handle your stuff and only reach out to you in case they believe the price of reverting their decision is too high.
  2. Provide guidelines as to how to prioritize and how to handle various tasks. The guidelines should be handed over to the person who you are delegating your work to, and also to the other team leaders who need your input.
  3. Prepare a backlog of tasks in advance. The backlog should be big enough so if someone does get stuck – they can pull another task to work on in the meanwhile.
  4. Reserve a one hour window per day that everyone can reach out to you with questions. Resolve conflicts at this time and adjust the guidelines if needed.


Most business trips last one week or two at most. If you grow your team properly – they should be able to handle this period without needing you by their side at any moment. With proper guidelines, proper priorities, big enough backlog and one hour per day for resolving burning issues – things should progress just fine.

And if not – then when you are back you’ll need to put some effort in making everyone more independent.

And sometimes, yes, there are gonna be some tasks waiting on your desk. On such occasions you’ll need to work a bit harder for a day or two, but I think it’s worth it.


Be grateful to workplace

It’s a great feeling to walk abroad knowing that someone else is paying for (almost) everything. Be grateful for that.

Never abuse it. For example – if your daily allowance is 70$ but you spent only 35$ never fill up a report a higher amount. I’ve worked with people who always filled the top amount each day even though they used much less.

Never treat a business trip as a way to increase your salary. If someone ever finds out – it can really stain your reputation.

Just be grateful.


Invest in gifts

When you’re going on a business trip, it’s not only the people from work who are going to miss you. There is also your family. This is becoming meaningful especially if you leave your husband or wife at home with the kids.

Doing it too often – and it might increase the tension in your personal life. You don’t want that.

Therefore, be generous with gifts. Always bring something back to your loved ones. Show them that you appreciate their effort.

If you have kids – bring them something as well.

Doing it properly – and they will be happy with you traveling (well… the kids at least), because they’ll be getting something from it as well. Just don’t be surprised that when you come back they won’t be rushing to hug you, but rather running to your suitcase 🙂


To summarize

Business trips can be a pain in a@#s or a big adventure. It’s all about your approach and state of mind.

If you prepare accordingly, take control over the preparation and adopt out of the box thinking – then you can make tons of fun in your business trips aside from creating deeper and meaningful relationships with your customers or colleagues.

I know I’m eager to get back on a plane!


That’s it for today!

If you found this post/series useful – please let me know in the comments. If you think others can benefit from it – feel free to share it with them.


Thank you, and until next time 🙂

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