The Vacation I Almost Skipped (What My Team Taught Me)

I almost skipped vacation this year. I just couldn't delegate enough. Here's how I managed to step away and what I learned about my team in the process.

Take a Break

Belle CommunicationsI almost didn’t take a vacation this year.

Since I have the luxury of being able to work from anywhere, I encounter the problem many entrepreneurs face: never fully unplugging. For this reason, I have learned to not count time away as “vacation” unless I’ve unplugged from work completely. And although I had hoped to fit some vacation time in earlier this year, due to new client opportunities, things didn’t really go as originally planned.

And so, my next opportunity to take a vacation was rescheduled for much later in the year than has been typical — the first two weeks of October. This two week hiatus made sense in theory because Daniel and I were already going down south for a wedding and it would mark our six year anniversary. From a business perspective however, the timing was less than ideal.

The Problem

For agencies, September/October marks the beginning of when we typically have requests for new business proposals looking into the new year. Brands reevaluate their current agencies and begin to allocate budgets for the coming year. Business development is one of my primary responsibilities and not one that I typically delegate. See the potential problem here?

Suffice to say as I neared closer to the beginning of October, when my schedule two weeks of real, honest-to-goodness vacation were slated to take place, I started to get uneasy. One of the reasons our clients love working with us so much is that they know they can count on us — I would feel horrible to give an impression that I wasn’t available at the beginning of a new relationship or when major decisions are being made.

Mind you, I have confidence in my team’s ability to cover for me (I’m thrilled to report they exceeded my expectations by the way) and I believe I’m quite good at delegating at this point. It’s just that I am typically leading the prospective client research and proposal build out process. It’s one of my primary roles and I really enjoy it. Not to mention it is one of the tasks that, although I typically would have the team help in research and ideation, I had not previously delegated the “lead” role.

All things considered, I was still determined to disconnect for two weeks if at all possible. I know from past experience that there is just no substitute for extended, unplugged time away. I always come back refreshed, energized and buzzing with new ideas. There had to be a way to make this work …

The Plan

In order for me to take this time away, I had to extend more trust and rely on leadership to help lead some new business proposals. This meant I also had to construct a game plan for situations I would typically handle on my own like determining when and if we’d submit for RFPs, how we’d finalize 2016 client PR plans and contributions to ongoing client strategy. In other words, top level outputs.

This would also mean, although I was still involved in the kick off and strategy before I left, the finalized proposals ultimately rested on my managers. To up the ante, this is the time of year when we get last-minute requests for proposals and often choose to band together as a team to execute them quickly and secure new business. In fact, as I was flying out and checking my email for the last time, I saw a request for a last minute proposal. My dreaded worst-case scenario.

Thankfully, we anticipated this potential challenge and my team executed correctly. Before leaving, we made the strategic decision that last-minute request for proposals (less than two weeks notice) would need to be postponed until after I returned. This meant we would require at least three weeks to complete a proposal. Typically, we turn things around in a week, so this was definitely an adjustment from the norm.

Although we could have rushed to make these requests come together while I was out, that’s just not how I want to run our business right now. So, at the risk of turning away a couple last-minute request (which we did in cases that were not the right fit for us anyway) we chose to adjust expectations with prospective clients to best allow us to research and tailor a proposal to their needs.

The Result

Nothing blew up. No one died. Clients weren’t angry or neglected. New business prospects were fine with our lead times. I was able to take a vacation and completely unplug because I had a plan and trust for my team.

This challenge ultimately helped me recognize that areas where I typically lead were, in fact, possible to delegate (or postpone) as needed in order to unplug. I also realized, although I prefer to handle my core responsibilities because I truly enjoy them and they are my strong suit, the rest of my team is willing and more than capable to rise to the responsibility and shine.

The BIG takeaway

When you have the right players on your team, they will step up, lead and rise to the occasion when given the opportunity. I experience new instances of this phenomenon every time I give up more of the reigns and allow my team to support our agency. I wouldn’t have seen this if I had not given them the chance to truly support me and our agency through the tangible opportunity of my being unavailable for two weeks.

So the next time you doubt your ability to delegate and unplug, ask yourself whether you really trust your team. Where there’s a plan, there’s a way. After all, aren’t we on this entrepreneurship adventure to be empowered to pursue our passions and enjoy life more than the 9-5 grind? Vacation shouldn’t be negotiable. Cheers!

Take a Break

Kate Finley

Founder + CEO of Belle
Currently thriving in Puerto Rico