So you want to go on a trip, but you don't know where to start. Your mind is creating barriers--it's not the right season, you don't have enough PTO to go on a long enough trip, you don't have a partner to go with, etc. As a lifelong perfectionist, I get it... what's happening here is that you know nothing is ever going to be as neat and tidy as it is in your brain, so you find little ways to self-sabotage (like procrastination).
First things first. The trip is NOT going to be perfect. Even my most carefully laid plans face hiccups. The bar that advertises itself as walk-ins only recently changed to reservations only. The day trip gets rained on, even though it's historically the sunniest month of the year. Southwest Airlines goes bonkers and cancels nearly all its flights. A lot of elements are simply out of your control. Travel is not so much an escape from life as it is an accentuation of it, both the highs and the lows.
As it's difficult for the anxious, perfectionist brain to relinquish control, I recommend making contingency plans for when things go haywire. When I'm making itineraries, I ensure that everything is planned out, and all dining and activities are pre-booked when possible; in addition to what I have planned, I scout out alternates in case something falls through. For example, some of my favorite bars don't take reservations for such and such timeframe, so I'll always select one or two alternatives nearby that I can hit up if need be. I've also learned to not schedule any highlight activities--such as a show, big tour, etc.--the day of planned arrival, in case there's a flight snafu. It's happened to me several times that I've lost money on something because I arrived a day late. (A word of caution on making your itinerary. It's easy to get so caught up in the details that nothing actually ever gets planned. I often approach my blogging with this same mentality--consistency must be maintained across every single page, I have to select the optimum font, etc.--but then recognize that, in the grand scheme of things, those details don't matter so much. So don't get so overwhelmed by planning that you procrastinate and get stuck. Just get started and things will fall into place as you go along, and if you end up at London's second-best restaurant instead of its first, it's going to be alright.)
Alternately--and I only do this for trips that aren't super big-ticket--I arrive in a new locale with NO plans. This frees me up to be spontaneous, to not feel the pressure to make things perfect, to be more casual and laidback. (Similarly, I'll often forsake nice clothes and makeup on a trip, which ensures that I'm not caught up trying to get the best, most curated photo of myself.) Or you could do a blend: go ahead and make that itinerary with contingency plans, but carve out time--whether it be several mornings, or a day, whatever pleases you--to go with the flow. Maybe even choose a word or a phrase that you want as the theme of your trip; I've seen people doing this for New Year's Resolutions this year and think it's the best idea. This gives you guidance without being so structured that you feel you've failed if you don't live up to every single plan.
Lastly, let me bring up something I'll call "embrace of mediocrity." Scrolling through social media, it's easy to get the idea that travel can be perfectly executed, all the time. This is blatantly false, of course. Acceptance of this fact, and even embrace of mediocrity, can help you to feel more confident in planning that trip. This is a bit counter-intuitive, but this hustle culture long touted by influencers intimidates people into inaction. Embrace of the mediocrity is not about not putting in your best effort, it's about propelling you to set yourself realistic tasks, to be more action-oriented. When I was writing my undergrad thesis, someone repeated to me some wisdom from an advisor: "The best thesis is a done thesis." Indeed, if we shift the focus from the perceived value of something (how well did I plan this trip) onto it being done (I have planned this trip), we are going to knock out our goals with a lot less fear and a lot more motivation.
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