Why I’m Scrapping The Five-Year Plan

“Where do you see yourself in five years?” was a questioned I heard a lot five years ago.

Back then, I envisioned myself working at an entertainment firm or in a large law firm.  As I made my way through the interview rounds, this prophetic question was the one constant I faced in life.

Upon hearing this question, as I sat in front of the interviewer in a freshly pressed suit, I oftentimes would think, “Well, ideally, in five years I’ll be married with a child or two.  We’ll live in a nice house and be surrounded by good friends.  My babies will go to church on Sunday.  I’ll live within 30 minutes of my parents.  I’ll be active in my community and life overall, will be good.”

In law school, they teach you not to answer the question that way.  As it turns out, generally speaking, most law firms don’t care about your personal life, at least when you’re a new associate.

So, time after time after time again, I’d say, “Five years from now, I envision myself being someone who attracts top-notch clients to the firm.  I imagine that I will be close to becoming a partner at that point in my career.  I want to be someone who has my own book of business and someone with whom clients trust, respect and want to work with.  I see myself as a leader in the entertainment industry, completing research into emerging trends and writing law review articles that are valued by my peers.”

Oh, how life has changed in the last five years.

Thank God.

In the corner of my condo sits a 5-foot tall tinsel Christmas tree.  I’m getting ready to leave Miami for the holidays, meaning I won’t be home to enjoy a fresh, pine-sceneted, real Christmas tree.  So, I settled for the next best thing:  An obnoxiously silver Christmas tree from my personal shopping mecca, Target.  The thing is gaudy and tacky and I love everything about it.

The presents sitting underneath my obnoxious tinsel Christmas tree speak loudly to how the last five years–or more accurately, year–have unfolded for me.  When I look underneath the tree, the bulk of the names scrolled on stickers attached to packages are those of people I didn’t know five years ago.  They are the names of new friends.  They are the names of new business acquaintances.  They are the names of ten children living in Haiti.

When I peak underneath my Christmas tree, what I see is the truest testament to what, unbeknownst to me, has been the mantra for my life:  Go with the flow.

If my best friends are reading this (hey, guys!), they probably just spit out their coffee upon reading that.  I know that if my mom is reading this, she also is probably on the floor laughing.  My dad is a little bit more gentle with my feelings, so he’s probably just sitting in front of the computer looking confused.  Each of them is probably saying out loud, “You think ‘Go with the flow’ is a phrase by which to describe your life?”  Fine, I’ll admit it:  In the grand scheme of things, “Go with the flow” and Alicia Jessop have never been synonymous.

I’ve been a planner my entire life.  In fact, I take planning to new levels and to places even the biggest of planners probably doesn’t even know exist.  You can ask any of my best friends about the email they get from me EVERY summer where I lay out about 50 activities we are going to engage in before Labor Day.  “On June 1, we’ll go boating.  On June 8, we’ll have a park day at Wash Park.  June 15 is a brewery bar crawl and let’s climb a 14er on June 22.  Oh, and we need to cross off every happy hour spot we’ve been wanting to try, so Thursdays are happy hour night and on Tuesday, well on Tuesdays, we’re joining a kickball league.  On Wednesday, I’ll have a bar-b-que at my house and we’ll play lawn games.  See you all there.  This is going to be the best summer ever.”

Being a planner for most of my life, I generally know the types of responses I will get when I fire off this email to my close circle of friends.  There’s my fellow planner friend, Megan, who says, “Awesome!  Looks good.  Let’s add X, Y and Z.”  There are my friends who have just come to accept that I’m neurotic and respond with, “Sounds fun!  I’ll come out as much as I can.”  And then there is my one friend, Brit, who’s honest.  Without fail, she zings me back an email saying, “Come on.  I’m exasperated just reading that.”  I laugh when I read her response and for a brief moment think, “She’s right,” but instead write back, “Brit, if we don’t have a plan, how are we going to get ANYTHING done this summer?!”

And therein lies my obsession with planning.  If there ever was a spokeswoman for the line, “Proper planning prevents poor performance,” it should be me.  (If you’re my agent and reading this, if we could get to work on that endorsement deal, that’d be legit).  For most of my life, I’ve lived under the belief that if I didn’t have a plan, everything would fall apart.  I wouldn’t have a job.  I wouldn’t have a roof over my head.  And arguably most importantly, my friends and I wouldn’t have fun.  To me, not having a plan–and not just a plan, but a well-crafted and immensely detailed plan–led only one place:  To destruction.

I operated under this belief until relatively recently.  I can’t pinpoint exactly what changed in me, other than to say that everything changed.  For some reason though, planning just stopped being important to me.  Instead, I decided to just start going with the flow.  And guess what?  The world didn’t end!  I have a roof over my head.  I eat every day.  And my friends and I are still having a really, really good time.

In going with the flow, my plans changed.  Clearly.

I’m not practicing law anymore.  I traded entertainment for sports. I’m a professor!  I’m living a life built up by three things I didn’t ever really see happening.

I don’t live within 30 minutes of my family, but I have a job that lets me see them for a good chunk of time each year.  I don’t rock my own babies at night, but my heart is full with love for a nation’s worth of babies.  I still haven’t found “the one,” but I’ve found love and hope to find it again.

All of these things happened without one thing:  A plan.  The life I’m living right now looks nothing even remotely close to what I envisioned for myself five years ago.  Yes, what I’m doing currently involves things that at some point in my life I obviously envisioned.  The difference, though, is that nothing I’m doing now is part of a hard and fast plan that I had.

The best part of all of this, is that I’m happier than I’ve ever been.  Ever.  And that’s what they don’t tell you about failing to plan.  Sometimes, failing to plan leads you to true happiness.

What I mean by that is this:  When you relax your plans, you ease up on your expectations.  When you ease up on your expectations, you give way for life to unfold for you in the way that it should.  When you hold onto your standards but give up on deadlines, perfection and specificity, a world of excitement and surprise has an opportunity to design a life for you filled with joy.

If anyone told 25-year-old Alicia that the thing gripping her heart the most right now was a group of orphaned children in Haiti, she would have said, “Yea, ok.  Right,” and moved on.  She wouldn’t have listened, not because she was a jerk, but because it would’ve seemed so far-fetched.

If anyone told 25-year-old Alicia that she’d write for Forbes and The Huffington Post and gain access to some of the greatest sports leaders in the world and dawn credentials for events like the Super Bowl, she would’ve said, “Yea, ok.  Right,” and moved on.  She obviously would’ve liked the sounds of this, but it would’ve seemed so far-fetched.

If anyone told 25-year-old Alicia that the most joy she would find in her career would be at the front of a classroom in Miami, she would’ve said, “Yea, ok.  Right,” and moved on.  She would’ve remembered the first time she was in Miami–when the city seemed so big and intense–and not have been able to see a path that would lead her to becoming a professor out of law school that didn’t seem so far-fetched.

When I look at life these days–whether it’s Christmas presents under my tinsel tree for new friends and babies in Haiti, the opportunities I’ve been given to cover sports stories or the chance I have to impact future sports leaders at the University of Miami–one thing becomes very clear.  And that thing is this:  My life began when I laid down my plans.

It did.

These days, I don’t stress about what’s next.  And for someone who lived the way I did for most of her life, some days, that’s hard.  Really, really, really hard.  Then I remember this:  The best laid plans can be destroyed, but some of the best gifts in life are surprises.

As 2015 approaches, I’m working, like many others, on resolutions.  And as it inches closer, what I’ve settled on is this:  I’m scrapping the five-year plan.  Actually, I’m scrapping the plan entirely.  I am done pretending like I’m a prophet for my life who knows what tomorrow holds.  Rather, what I am going to focus on is the person I can become.  Instead of making plans for my life, I’m going to work on being the person I want my life to be defined by.

Am I joyful?  Am I giving?  Am I kind?  Am I honest?

Am I happy?

If any of the answers to those questions are “No,” I know it’s time to change.  I know it’s time to shift what I’m doing and move forward.  I know it’s time to get on with things and to take myself and my life down a new path.  I know it’s time to perhaps go somewhere and do something that I never planned.

Sometimes I wish I had a time machine.  Sure, I wish I had a time machine so that I could go back in time and take back some of those decisions I’d later come to regret.  Sure, I wish I had a time machine so that I could go back in time and see historical events and walk alongside history’s greatest leaders.  Today, though, I wish I had a time machine to zap me back to a place that I really didn’t want to be in the first place: Those stuffy law firm board rooms.  If I had a time machine, I’d want to get back there, because five years later, I finally have the best answer to that age-old question.

“Ms. Jessop, where do you see yourself in five years?”

“It’s funny you should ask that, sir.  It’s funny, because I see myself somewhere you probably don’t expect me to be.”

“Oh, really?  Indulge me.”

“Certainly.  Well, after giving it some thought, I know where I see myself in five years.  And when I look forward and when I look at my life and the person I want to be holistically, what I see is this:  I see myself scrapping the five-year plan entirely.  And in doing so, I plan on doing something different, something that maybe isn’t the most rewarded or even respected in this industry.”

“And what would that be, Ms. Jessop?”

“I see myself living.”