Reinventing Your Life? Here’s How to Deal with Failure (and It’s Going to Happen)

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When we’re making changes in our life, failure is inevitable and can even be a good thing even if it doesn’t feel that way at the time. Here’s how to deal with failure, overcome obstacles, handle setbacks, and come back even stronger.

Who remembers my wildly successful weight loss challenge from 2015? You know, the one where I tried out a different weight loss plan each week and then blogged about all the weight I lost?  Don’t bother trying to find it in the archives, by the way. I just deleted the whole series.

If you don’t remember it, don’t feel bad. Maybe you weren’t one of the 30-40 people visiting my blog each day during that time. Or maybe you don’t remember it because even though I turned my life inside out for four weeks in an effort to lose weight, I ended the challenge not even one pound lighter. What a good time that was!

I’m thinking about that series now because I’m going through a blog clean-up and deleting posts that didn’t benefit my readers. Deleting those posts caused me some serious pain. And even now, a bit of chagrin. After all, I spent six weeks on the series. In fact, I was so disheartened after the challenge that I didn’t blog again for a month. I had this vision that the challenge would benefit me personally – I would totally lose at least 10 pounds! – and on the blog – my weight loss success would bring me a ton of new readers! Instead, I failed in front of my 40 readers. And the fact that I still had only 40 readers was just salt on the wound. Salt that was apparently making me retain so much water that I couldn’t lose weight no matter how much I tried.

But the thing is, I did blog again. I spent time learning how to be a better writer. I spent even more time learning how to be a better blogger. I kept going and I even found a way to lose weight that worked for me.

It’s especially important for midlife women to remember the importance of persistence in the face of failure because midlife is a time of change. We’re aging; often in surprising and distressing ways. Our children are growing up which can also be a little surprising and distressing. Many of us are contemplating career changes. We’re frequently looking at ways to shake up and reinvent our lives during our second half.

And with change; inevitably comes failure.

It’s so easy to read articles about the benefits of failure and to nod your head in agreement, isn’t it? Yes, yes, of course, if you’re not failing at something, then you’re not thinking big enough, am I right?  And I’ve read so many stories about successful women who have overcome hard times and persevered that their struggles simply seem like a plot point: here’s the part where she gets down to her last $10.00 in the bank before she finally sells her first mop. And now she’s a millionaire!

But it’s so much harder to actually live through a time when you tried something and failed at it. Your struggle isn’t a lesson you needed to learn or a dip in the road before you triumphantly reach your goal. When you’re actually in the moment, you don’t know how things are going to end. This might be the dip in the road before the fall off the cliff. And the moment isn’t scary. It’s terrifying. Or heartbreaking. Or so mortifying that you just don’t ever want to surface in the real world again.

Midlife is a time of change. And we sometimes fail when we try new things. As midlife women, we need to become comfortable with change and failure if we want to thrive.

If you’re currently feeling depressed and downhearted because you took a risk and it didn’t work out, there are some things you can do to deal with your failure and get back on track. Here are some things to try when you’ve failed and need to move past it.

Take Some Time Off

Sure you’ll want to keep going toward your goal, but you’re allowed to take a break. If you took a chance on a dating app, only to meet a bunch of frogs and no princes, it’s fine to take a bit of break if want. My blogging break after the series that failed helped me clear my head, come up with a new strategy, and get back into the game with renewed effectiveness. A small break can help renew your enthusiasm and refuel your energy.

Midlife is a time of change. And we sometimes fail when we try new things. As midlife women, we need to become comfortable with change and failure if we want to thrive.

Remind Yourself: You Had a Setback, but You Are Not A Failure

If you’ve tried something new and it hasn’t worked out the way you wanted, congratulations! If your identity for the last twenty years has been as a mother or wife or working in a field that no longer excites you, then you’ve developed a sense a competence around that role and when you move to the next thing, you’re going to sometimes feel incompetent and lost. And you will make mistakes. How could you not? You’re doing something new.

But, after decades of feeling competent, it can be very easy to feel that your mistake means that you’re a failure in your new role and you should just go back to your old ways. Don’t fall into that trap! You’re not a failure! You had a setback and that simply means you need to continue on.

Take this Opportunity to Examine Your Strategy

I recently read an article about how Jeff Bezos took the failure of Amazon Auctions, which was an attempt to create a part of Amazon that was an eBay-like auction site, did some tweaking and turned it into Amazon Marketplace, the wildly successful part of Amazon that allows third-party sellers to sell via Amazon.

Instead of scrapping the whole idea when it failed, he looked at what worked and what didn’t and turned it into a new idea that worked really well.

Midlife is a time of change. And we sometimes fail when we try new things. As midlife women, we need to become comfortable with change and failure if we want to thrive.

You can do the same with your failed idea. (This is where a break comes in handy; it’s much easier to be objective when a bit of time has passed.) For example, Midlife Rambler became a successful blog only after I took some blogging classes and learned how to write blog posts that met the needs of my readers. As it turns out, millions of people don’t want to read the random musings of a fifty-year-old woman. This was hard, but necessary information, to learn.

Midlife is a time of change. And we sometimes fail when we try new things. As midlife women, we need to become comfortable with change and failure if we want to thrive.

Just Keep Going

Perhaps the most important tip for overcoming failure is this one. Don’t let failure make you stop.

It’s more important than ever to start trying new and possibly scary things. At midlife, whether you like it or not, change is coming. Our children are growing up and moving on and soon enough, our careers will start winding down. If we don’t also change then we’ll become stagnant and depressed.

And so here’s the thing you must remember as you go plan the next half of your life. There’s no better feeling than when you master something that was previously hard and scary. When you take a trip alone for the first time and realize how freeing it is to plan your own selfish itinerary. When you run your first 5K after years on the couch. When you learn to speak French as an adult. These are the moments we’ll be learning to savor during the coming years.

P.S. My absolute favorite story of a woman who learned a new skill in midlife is this Twitter thread about the Mother-in-Law who secretly learned to play the violin at 64. If she can do that, you can do anything you want to do. You can read the whole story here.

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Katy Kozee | Midlife Rambler

Hi! I'm Katy and I started Midlife Rambler when my youngest child was a senior in high school. I was staring at the coming empty nest and wondering what was next for me. Does that sound like you? Then you’ll love our community of fun, feisty women. We’re looking forward to finally focusing (just a little) on ourselves and talking about all the things we enjoy: fashion, beauty, travel, entertaining, and being the best possible you.

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