I shall begin this post with full disclosure of two things:
- I'm not over 50 (I even have a few weeks during which I can say, "I'm not over 40")
- I sometimes operate in a way that some may consider risky, or possibly even nuts
But I have been asked to discuss how one should go about making a later-stage career change. And I like that someone is considering such a thing. So I've given it quite a bit of thought.
My two cents (actually, it's more like 11):
If you're getting up every day thinking, "I am not living my calling. I have more to offer. I know exactly what I want to be doing and I'm not doing it?" I think you should strongly consider a bold, well-thought out move.
If you just don't really like your boss, or hate the food in your office lunchroom, or think the lady in the cube next to you talks too much? I'd actually think long and hard before you go all crazy and launch your day job.
There, I'm being conservative in my advice.
But really? It's the truth. I think that, for those who have a deep longing, a clear dream or a master plan that you've just not yet executed (because you're tired, or scared, or it never seems to be "the perfect time")? You are in a much better position to make a dramatic, late-career shift than someone who just wants to get away from the jerk that takes your parking spot every morning.
Assuming you are in the former category? Let's proceed...
I'll argue that you can begin planning pretty much anywhere. The key is to just get moving. And keep moving. Your second job has just become planning your next career move. Treat it as such.
You need a plan. It doesn't have to be some 754-page blueprint with every possible contingency detailed out to the most finite detail. But it does need to map out such things as:
- The roadmap required to get where you wish to go (think schooling, funding, training, etc.)
- The benefits you know in your heart will come from making this shift
- The risks involved in making this shift, and how you can mitigate them
- The moolah required to make this move -- startup costs, and how you're going to cover the living expenses as you ramp up
- The people in your network who will likely be helpful in helping you make this transition - Now's the time to dial 'em up. (Please tell me you're using Linkedin. Please.)
- How the key people around you are going to respond to this change. Seriously, change it tough for people, especially those who aren't choosing the change. You've got to think through how your core peeps are apt to react...and how/if this will impact your road map. Prepare for resistance, especially from those who really, really wish they had the guts to do what you're about to do, but don't. These are the ones who will likely try and make you feel like a fool for proceeding. Just be ready for that. Is all.
I'd also spend lots and lots of time online, researching and communicating with people who have made similar career shifts, and have done so successfully. No better way to make you realize how doable this is than to chat with those who blazed the trail before you. These folks will also be happy to share with you the "wish I'd have know then.." stories that may help you avoid unexpected pitfalls in your own transition.
You can do this. And just think about how cool your kids and grandkids will think you are when you pull it off. Good luck, and if anyone makes this move, I want to hear from you.