My brother and I were chatting on a recent car ride about how crazy the curveballs that life throws you can be. I sort of joked that I hadn’t really had a life plan since I was 23 and I’ve mostly been winging it since then.

He pointed out that it’s best to never get attached to anything since plans change all the time.

This got me thinking about some things in my life that did not go according to plan.

College 

Sometimes, I’m kind of delusional. I applied to several ivy league schools after high school. I was rejected by all of them and wait listed at a top liberal arts college. I wound up at some no-name state school in the middle of the woods.

I hated my first year of college. I had no idea what I was doing with my life. School in the middle of the woods without a car was really boring. Then I accidentally took the wrong class in the spring of my freshman year and the rest is history. I switched majors to theater. I made a ton of friends who I’m still really good friends with. That South Jersey area is still where I’d probably like to wind up one day.

Relationships 

Once upon a time I was dating a guy studying to be a pastor and we were going to get married and move to upstate New York and plant some churches. I was all in on that plan. Then everything fell apart and I wound up in San Francisco (if you missed that post, you can read it here).

If all of that hadn’t happened, I never would’ve learned that there’s a big difference between how you “have” to live your life, according to the people around you, and how you have to live your life. Like – you need some food, and some shelter, and pretty much everything else is negotiable.

IRA 

When I first went to open an IRA, I just thought, “I guess I’ll open this retirement thing.” Turns out, I had to have several thousand dollars saved up first (this isn’t true these days – there are plenty of low deposit or even no initial deposit IRAs). So I had to work at that plan a little and it was one of my first experiences with saving money with a purpose.

Grad School 

I’ve wanted to be a theatre professor since I was in college. I looked like the coolest job to me – you get to spend all day talking about theatre and you can put on crazy performances in colleges because it’s about learning different styles of performance more than making money most of the time.

So I’ve applied to doctoral programs twice and didn’t get in either time. The first failure led me to spend a year in England working on a Master’s degree instead and learning all sorts of fascinating things. The second failure led me to the job I have now, which is pretty terrific.

Sometimes when things don’t go according to plan, Plan B – or C or Z – the alternative isn’t always so bad.

Has life ever thrown you a curve ball that worked out well?