"Work It Girl!" – Tania Doub

Vacation vs. OOTO

It’s not the first time a prospect meeting has reared its ugly head right in the middle of our vacation.   In fact, it feels more like Murphy’s Law than just a random coincidence.  Bad timing, always.  In fact, it’s always the worst timing!

Murphy’s Law. A rule that states, “If something can go wrong, it will.” An addition to this law reads, “and usually at the worst time.”

There have been countless times over the last decade or two where I’ve taken calls from the car en route to the mountains for a ski weekend (with spotty cell service) or popped into the hotel for hours on end with the excuse of “having to use the bathroom real quick,” while my family plays poolside.

In fact, at my last job, the last week of the quarter was not just any ordinary week.  It was March break.  MARCH BREAK for Christ’s sake! It was one of the sacred family vacation weeks when my kids were out of school and we could plan some much needed down time together… and that particular year I was in the process of closing the largest deal in the history of the company with Estee Lauder.  Globally!   We had planned to stay close.  In the U.S. somewhere close to a major airport.  And cell service was a must because I knew the bulk of the contract negotiations were going to happen sometime during that week.

On said day, I had pleaded with my boys to do ski school so that John didn’t have to manage two mavericks speeding down the hill by himself.  Then I had lovingly convinced him that doing multiple runs down the mountain by himself would in fact be “very peaceful” and “just what the doctor ordered.”

Have you ever tried negotiating a contract call in ski boots?  I have.  And it’s very uncomfortable.  I hadn’t bothered to take off the boots because honestly I remember thinking it would be more trouble than it was worth.  But I also hadn’t banked on the call going for 3 hours! Needless to say my toes were purple and numb when I finally finished the call, and that’s precisely the moment I had to jam my laptop into a rented locker and hit the slopes pretending I had enthusiasm and excitement for the afternoon – still in my boots.  Three days later I closed that deal.  I inked the largest deal in the history of the company and got a personal phone call from the CEO congratulating me on the deal.  But anyway, that was then and this is now, and in sales you’re only as good as your last deal…so moving on…

To be clear.  I wouldn’t get distracted for just any call.  These are not calls that could have waited for when I finally remove my OOTO.  They are not calls that could have been rescheduled.  They are not calls that could simply be ignored for another day.

They are THE calls.  THE emails.  With THE prospects.  And THE difference between whether I made my number that quarter. Or not.   Plain and simple.

In fact, just earlier today (on our family vacation) I received an email from a prospect who is forecasted for my quarter and it simply says “Tania, can you provide a pricing estimate? It needs to be received by EOM so that we can hold a place in the budget.” End of month? That’s tomorrow?  “OK. No problem!” So I prop open my laptop and start typing away furiously while my husband and boys come over to my pool chair and excitedly declared “Did you just see our Doub cannon ball off the high dive????” Oops… no.

The truth is, when you sign up for a sales job, you sign up for a life of being on the clock 24X7, on demand.  The reality is, in sales, when they (the prospect) wants to talk to you… you make the time.  Anytime.  Every time.  Because that’s ultimately the difference between closing a deal, making your number, and actually getting paid!

This week was no different.  It’s the week before Labor Day and time for our annual vacation to Maine.  The kids LOVE this vacation.  It’s the final hurrah of our summer before the kids head back to school and we kick back into work mode.  We have been back at this resort three times already.  I guess you can technically coin this trip “The Annual Doub Vacation!” We booked this week in February, over 6 months ago.  The resort is easy.  Arcades, s’mores, tennis, 2 pools, and “the best oatmeal EVER!”  To say we were excited is the understatement of the century!

And there it was.

Segment bought 8 seats to the 2019 U.S. Open.  This is an incredible opportunity to network and entertain prospects and customers in a completely social and utterly exclusive setting.  I can’t say for certain how much we paid for these seats, but I’m pretty sure they far exceeded the average ticket cost of a sporting event.  The date? Thursday, August 29th.  Right smack dab in the middle of “The Annual Doub Vacation!”

While not mandatory to attend, it’s most definitely the social setting to make connections and use it as a sales tool to advance my deals.  While I sent out multiple invitations, I was laser focused on getting only 2 companies to attend.  One was a customer (whom I had just closed a deal with just 3 weeks ago).  And one was a prospect.  Both were on my key target account list.

I remember hypothetically mentioning it to my husband over dinner the night I found out.  Slowly trying to get him acclimated to the idea of me sabotaging our family vacation while I outwardly tackled the debate in my own mind.  “Segment bought tickets to the U.S.Open this year.  It happens to fall right in the middle of our vacation.  What would I do? Not go, right? Yeah, of course I wouldn’t.  It’s our vacation.  But I could use the opportunity to get my prospect there and that could seal the deal.  It’s a big deal.  What would you do???” To which he casually smiled and replied, “I know you will do the right thing…”

Well what the heck is that supposed to mean!?

OK.  I thought to wait at least a few weeks before I made any hasty decisions.  I figured I would simply send out my invites and whatever happens, happens.  Except then I got to work just moments later.  In those few weeks, I managed to google “airports in Maine” and map out every flight route from PWM (Portland), to BGR (Bangor), to RKD (Rockland) to PQI (Presque Isle) to New York airports including LGA (LaGuardia) and JFK (John F. Kennedy).  I called our hotel and adjusted our vacation dates so that we leave Saturday (instead on Monday) and return Wednesday (instead of Friday).  And I had mapped out Uber rates from our hotel in Maine to the various airports so that I could sneak out (if need be) for a quick day trip to New York.  As the days crept closer, the RSVP’s started coming in… they were all “YES.” And just like that, I was sneaking out on part of our family vacation to go to the U.S. Open.


Except fast forward to this week, and in a random twist of fate, all that planning and the 3 “YES” RSVP’s later…Murphy’s Law had finally reared its ugly head.  And this time it was in my favor.  Each of my invitees had a different – and unrelated reason – they unfortunately could not attend, after all.  Each of them apologized profusely and we made other arrangements for alternate meetings and network opportunities in the coming days.  Segment filled the seats with alternate prospects.  And most importantly, I didn’t have to abandon my family vacation for a tennis match.  (By the way the weather forecast totally cooperated too! The sunniest days of that whole week turned out to be Saturday through Wednesday; our adjusted vacation dates.  I guess I did the right thing after all, didn’t I, John?:))

When duty calls, I run.  If it’s work-able, I find a way to make it work.  It’s the way I’ve always been.  Even if it means turning my life upside down because of it.  I wish I could say I had a job that allowed me to just shut it off.  But I don’t.  What I can say with certainty though, is that the job that I have is part of the reason we have been able to plan ski weekends, pool getaways, Maine trips, and even a trip to Disney I announced to the family after I closed one particularly intricate deal  – to which my kids responded “DO THAT AGAIN MOM!!!”

Sitting here with my laptop and phone nearby, this time I hear “MOMMMM!” And I look up to see my boys waving to me as they jump off the high dive.  Then I hear Johnny’s voice, “Christian, close your eyes! It won’t seem so high!” And a loud screech as they plunge 10 feet into the water.  I see the big jump off the high dive this time.  And it’s glorious.

I realize, in that moment, that whether I’m working or not – my boys know my rhythm.  And I know theirs.  It’s the perfect summer vacation after all!

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