6 Questions to Help You Avoid Regret and Live with Greater Clarity in 2016

I hate regret. It’s an awful feeling. As I look back on this past year, if I’m really honest, I have some regrets. There are some things I did well, but there are also some things I wish I could go back and do differently. There are areas of my life I wish I’d given more attention, and others I wish I had focused a lot less on. My disdain for regret is one of the reasons I have a love-hate relationship with the end of the year. The end of the year is a time to look back as we prepare to move forward. This is not always a painless exercise. It takes courage to look in the review mirror and honestly assess what we see, but I believe it’s absolutely necessary if we are to live next year better than the last. And that of course is the beauty of a new year. It is a chance to start over. The beginning of a new year bring with it the opportunity to learn from our mistakes, to turn the page and to begin a new chapter.

So for those who like me want to live this next year better than the last, this post is for you. And to make this personal and prove I’m not just blowing smoke, I’ve also included some brief reflections in italics on how I am applying these to my own life in the coming year.

Here are 6 questions to help you avoid regret and live with greater clarity in 2016:


1. What would you do if you knew you couldn’t fail?

Fear can be a powerful motivator, can’t it? It can be used to get people to watch a show, buy a product, click on a link, read an article, give to a cause or submit their vote. For better or worse, fear is powerful. It can just as effectively move us to action as it can paralyze us in our inaction. If we’re not careful, it can be the very thing that keep us from doing the things we were created to do. What would you do if you knew you couldn’t fail?

Personally, if I knew I couldn’t fail, I would do a lot more writing. So this year I’ve made it my goal to push past fear and keep taking risks with my writing. Specifically, my goal is write and share one article per week and to complete and publish one e-book. (Did I really just share that publicly? Gulp. Moving on..)

2. What hills are you willing to die on?

Each of us has an endless variety of interests and opinions, but very few hills we are willing to die on. These are the beliefs, ideas, convictions and passions that you count worthy of your life’s greatest investment. What is your hill? The answer to this question brings a tremendous amount of clarity about what really matters to you. It is the thing that stands above all other things. If you can get clear on this, it’ll become the filter through which you make crucial decisions about what you will say yes to and what you will say no to in the coming year. What hills are you willing to die on?

This probably doesn’t come as a huge surprise to those who know me, but my hill is Jesus Christ – his gospel, his church, his kingdom. This last year I gave too much of my time and energy to other hills. Some of those hills are good hills, but not good enough to be worthy of life’s investment. They aren’t the hills I’m willing to die on; and dying is precisely what we’re all doing a little bit each day. So this year Megan and I are refocusing on Jesus’ great commission to make disciples. For us this means prioritizing relationships with a small group of people as we seek to learn from them, invest in them, and participate in God’s blessing work in our city alongside them.

3. What do you need to add to your stop-doing list?

This is an idea I stole from Jim Collins and it is interconnected to the previous question. Once you know the hills you are willing to die on, it’s time to start living like it. For most of us this is going to require making time – something most of us are already short on. I imagine this is why so many people opt out of New Year’s resolutions or at least give up on them so quickly. We are all incredibly busy and adding more things to our already full to-do list doesn’t seem feasible most days. This is why it’s so important that you identify the things that you are going to intentionally and mercilessly cut out of your life. Everybody’s got a to-do list. Now it’s time to make a stop-doing list.

I believe this particular point is so important that I’ve committed to continue working on it throughout the next month. My list is far from complete, but it’s been helpful for me to think about this categorically in my own life. What do I need to stop doing personally, vocationally, relationally, habitually, maritally, etc? In other words, what good (or perhaps not so good) things do I need to cut out to make room for the best?     

4. If you could relive 2015, what would you do differently?

This one takes real courage to answer honestly. And if you’re tempted to point out that there’s nothing you’d do differently because you live your life in a “no regrets” sort of way, I’m going to go ahead and call your bluff on that one. None of us live life as mistake free as our carefully curated Instagram feed and YOLO hashtags would have others believe. The truth is last year you made mistakes and so did I. We all did. And the only way to ensure we don’t repeat last year’s mistakes is to acknowledge them for what they are and learn from them.

The biggest mistake I made last year was in the area of friendship. This last year I walked through some pretty significant depression and anxiety and as I did I made the massive mistake of isolating myself from some of my closest friends. I didn’t make time for them. I didn’t reach out. I was distant and largely unavailable. This year I’ve committed to not repeat that mistake. This year I’m committed to being a much better friend.

5. Instead of asking what will be most important tomorrow or the next day, ask what will be most important on your last day?

When people come to the end of their life their greatest regrets rarely have to do with work and almost always have to do with relationships. Rare is the person who wishes they could rewind the clock to go back and hustle a little harder, put in more late nights at the office, or sacrifice more for that extra bonus or promotion. Many people, however, would do almost anything to go back and invest more time and attention in their loved ones. This is a lesson that you can either choose to learn now or later. It’s your choice.

This year one of my goals is to consistently make memories with my family. Specifically this means quality time with Megan, monthly daddy-daughter dates, a vacation together in the fall and working far enough ahead to take Saturdays off.

6. What do you really want? 

If you could suspend reality for a moment and dream a dream, where do you want to be 5, 10 or 15 years from now? What would your life look like? What kind of person would you be? Do you have that picture in your mind? Can you see it?

Now what daily habits can help you start moving in that direction?

Ours is a culture of fast food, instant oatmeal and high speed internet. We are not accustomed to waiting. We want what we want and we want it now. If we can’t get it, too often we give up on it or assume it is unattainable. As Craig Groeschel rightly points out, we often overestimate what is possible in the short term and greatly underestimate what is possible in the long term. What do you want? If you can get clear on that and are willing to practice some daily habits to work in that direction, I think you’d be surprised at what is possible.

One of our goals is to be completely debt free fifteen years from now. We can’t get there quickly, but we can get there in time, if we are intentional. For example, we’ve made some daily habits to help us get there, such as: not eating out too much, driving old cars that are paid for, going without cable tv, not buying expensive toys, not taking on new debt or financing things we don’t need, practicing generosity and investing a percentage of our income. It’s only been in the last few years that we have begun these habits and we didn’t begin them all at once. We added them one by one. It hasn’t provided us with instant wealth or some of the luxuries I’m sure we’d enjoy, but they are small habits that are moving us in the direction of where we really want to be down the road

How about you? Where do you want to be? What daily habits can you start practicing that will help you start moving in that direction?

On Purpose

There are some who will say they’ve given up on New Year’s resolutions and goal setting a long time ago. It is usually spoken with a smirk, as if they already know something you too will eventually figure out. They might add they are just a realist, but let’s be honest, a realist is just a cynic who is trying to make himself feel better. Don’t take the cynic’s way. Aside from being hit by a bus or some other unfortunate event, you ARE going to live 2016 and either you are going to live it well or you are going to live it poorly. You may not accomplish everything you hope to this year but I can guarantee you will accomplish exactly 0% of the goals you don’t make this year.

Twelve months from now you’re going to end up somewhere. It might as well be on purpose.

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