What’s one thing you wish you had started doing earlier in life?
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There are a lot of things I wish I had started doing earlier in life. I’ve always described myself as something of a late bloomer. As a kid, low self-esteem meant I was shy, awkward around girls, and probably a little late to the party when it came to dating and some of the other milestones that come along with relationships.
The Timeline of Fatherhood
I don’t want any of this to be taken the wrong way. I have zero regrets whatsoever when it comes to my boys. I love them dearly and I can’t imagine an alternate universe where they either don’t exist or aren’t the exact people they are.
Take my first marriage, for example. I was 26 when I got married—not terribly old, but not terribly young either. As far as age goes, I think that was a pretty good time for me to settle down. But X1 and I were married for seven years before we finally had Kid 1. Granted, that was a conscious decision; we liked our lives the way they were and weren’t looking to have a child terribly soon. Still, sometimes I have to wonder what my life would look like if I had started a family a little bit earlier.
Likewise, I have no regrets regarding Kid 2. In fact, back when I was with his mother, I really thought everything was going to work out, and that was going to be my second (or even last) shot at happiness. She and I had talked about having two children together, preferably one boy and one girl. We got halfway there with Kid 2. But I was 40 when he was born, and I learned real quick just how much I had aged in the seven years between Kid 1 and Kid 2. Having kids isn’t easy, and as the parent doing the heavy lifting with a baby, you really don’t sleep much. Evidently, seven years was just long enough for me to completely forget what that felt like.
Even so, being an older dad came with its own advantages. I do think that, even though I was a little more tired and maybe a little more grouchy at times, I brought a level of patience to being a parent that I didn’t always have in the beginning with Kid 1. I was never grumpy or angry with him, but I didn’t have the experience of raising Kid 1 to carry me into raising Kid 2. That helped immeasurably. Looking back in hindsight—and knowing what we know now about Kid 2 and his autism diagnosis—it certainly explains some of the frustrations we had with him earlier on with things like sleeping through the night. But it’s absolutely different the second time around. Both of my boys are unique individuals, of course, but learning on the fly is one thing, and learning some new tricks with years of experience under your belt is a whole different matter entirely.
The “What Ifs”
If I’m really looking at the “what ifs,” though, the answer to what I wish I’d started earlier is easy: Sierra. I would’ve asked her out about seven years earlier. I do think that if I had gone out with her back then, I would’ve ended up on the sidelines, just like her ex-boyfriend “The Meathead” is now. I was just like him in a lot of ways, but I didn’t have the initiative, drive, and motivation back then that I have now—traits I think would’ve been a turnoff for her anyway. I still remember to this day the first time we hung out and I told her I was looking to do graduate school, and her face just lit up.
Don’t get me wrong; I am so grateful for where Sierra and I are today because I think the universe lined up the way it did for a reason. I don’t think either one of us could be bringing what we are to the table if we hadn’t had the experiences of the last seven years. But still, sometimes you gotta wonder.
Striking First
More than anything else, I wish I had cultivated more confidence from an early age. I wish I’d realized earlier on that I was going to have to stick my neck out on the line and take the risk of rejection in order to experience the exhilaration of victory.
The thing about building and maintaining confidence is that it’s forged on a string of successes—or victories, if you will. When you never put yourself out there, yes, you protect yourself from the fear of rejection, but you also cheat yourself out of a chance to achieve victory. Some people are comfortable playing it safe for their entire lives. I just wish I hadn’t been one of them. I wish I had taken those chances at a much earlier age.
It took me too long to realize that you simply have to put yourself out there; you have to just go for it every now and then. Yes, you’re going to fail. But you’re also going to succeed, and there is nothing in the world quite like that feeling. There is nothing like that burst of confidence straight to your psyche.
Rebuilding a life takes grit, consistency, and a lot of ‘Option C’ thinking. Having crossed the 1,000-day milestone, I’m now charting the territory beyond. The mission remains the same: No glitz. Just the work. New to the blog? Start your journey here to see the blueprint and the ‘Tricorder’ perspective behind the rebuild.
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The article “From Late Bloomer to Going For It: Lessons in Confidence and Timing” first appear on Rebuilding Rob.


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