It only matters if you don't want to work for the rest of your life.

Honestly this is what it all boils down to. Do you want to work for the rest of your life? No? then live within your means and invest. Debt isn't a bad thing but it will keep you employed longer than you might like and investments are one of the only ways you are going to keep up your desired standard of living....or possibly even improve your standard of living.

I get it though - when you are in your 20s or even 30s retirement seems like a freaking lifetime away - let future you deal with that, am I right? You are just starting out your career or making the kind of money that you can really start having fun with...why get all boring and start socking it away for the future? well...because future you is staring at you with grumpy face right now telling you to get your shit together and do it because it will make the whole song and dance SO MUCH easier for the long haul. Ok ok....it's future me staring at 20s me with grumpy face shaking her head saying 'seriously...HOW...HOW...did you manage to spend all your money AND THEN SOME so I now have to pay off your debt and save even more just to make up for it?'....20s Jen hangs her head a little but I can see her slight sassy smile that regrets nothing. When I talk to 20 somethings who are already on top of their finances and investing I simply applaud them. It's not the only way, but it's a damn good way to kick off adulting.

Now that I am in my mid/late 30s and connect with many in their 40s and 50s the relationship with money has evolved as much as any other relationship in our lives. We now want money for the long run, we don't want the thrill of wondering if it will be there for us or not, we want to know that we have a lifelong relationship, we are in this together, and through ups and downs there is trust that no one is leaving the other. This means we have to pay attention to our money now. However, as with any relationship, it varies from person to person. Some are lucky in money love, others work really hard at it, some do 'ok', and others neglect it altogether and will be perpetually seeking that feeling of comfort with money until they are ready to settle down and commit to the relationship.

So if you don't want to work for the rest of your life you have to live within your means and invest and if you want to do that in a way that just feels right (a.k.a doesn't suck) then you need to commit to your relationship with money. Show it respect, give it some attention and it will respect you back and stick around.