“Give me $100 at the beginning of the week,” said my friend Leonard. “At the end of the week, we’ll look at your list. If you’ve achieved everything on your list, I’ll give you the $100 back. If you’ve achieved only 50% of the things, I’ll give you $50 back.”

According to Leonard, this is something that has worked successfully for another friend of his, to stay on target with his personal goals around fitness, self-care, wellness, etc. Apparently for Leonard's friend, money was his strongest motivator. But as strange as it may seem for an entrepreneur and die-hard capitalist like me, at the end of the day, money doesn’t really motivate me.

All the same, with the new year approaching and a list of self-care rituals that I habitually ignore, now seems like the time to figure out what WILL motivate me to get on the stick about my own well being.

For parents and entrepreneurs alike (not to mention those of us who are both), self-care can be the hardest thing to justify making time for. There is no outside source of punishment or reward, and at the same time, every minute of time you take for yourself feels like it's in direct competition with the things you have to do for other people — your kids, your investors, the users of your product, your team. It’s easy to de-prioritize self-care generally, but especially those daily things — meditating, working out, even getting a full night’s sleep every once in a while — that don’t result in an immediately visible result to you or anyone else. And yet it is arguably MOST important for those of us with ultimate responsibility for keeping the ship afloat (be it our families or our companies or both) to care for ourselves like we would care for any other person whose well being we’re responsible for.

I tend to get a lot of grief for using a business mindset to tackle personal problems. But I stand by the fact that solid problem-solving techniques work because they work — on any kind of problem, whether professional or personal. One of the best things we implemented in 2019 at Nanno was a workflow management system called OKR (which stands for objectives and key results). We set a single main goal for the team for the quarter, and then set priorities every week for what we will each do to reach that goal by the end of the quarter. On Mondays we have planning meetings where we decide on the “sprint” for that week — the specific things we’ll accomplish that week — and on Fridays we have a “wins” meeting where we show off what we’ve accomplished.

The primary purpose of OKRs is to help your team focus on your company’s most important goals — which is obviously hugely important — but for me, the real value has been the creation of a culture of transparency and accountability. Our team sets goals together, and then we evaluate our progress toward those goals together. Working toward a single high-level common goal helps us celebrate each other’s wins and makes us extra excited to show off our own. And when we’re falling short of meeting our goals, it’s motivating (in a good and bad way) to know that we’re going to have to come clean about it at the end of the week.

“I think,” I said to Leonard, “the thing that motivates me most is being a good role model for my kids.” This is the standard against which I measure almost all of my actions and motivations (more on this another time). And if it’s important to me to set a good example for my team at work through transparency and accountability, it’s twice as important when it comes to my kids.

So here is my plan for helping myself and my family focus on and achieve our personal goals for 2020.

1. Have a family meeting at the beginning of the year where everyone sets their goals. For this year, since my kids are still young, I think our family’s goals will all be routine-based — I want to meditate and do yoga every day, get to Krav Maga class at least once a week, and do some form of intense cardio (other than Krav) at least once a week. For my older daughter, there are a handful of chores she has to do every day and she needs to be more religious about practicing her violin. For my younger daughter, she has some chores too, and needs to focus on making sure she’s reading every day. I think for us, those daily and weekly goals work better than more abstract long-term goals, but with older kids, setting a longer-term objective (monthly or quarterly) might be a good way to help nurture long-term planning and tenacity. The important thing is that everyone fully buys into their goals and feels excited by the vision of what life will look like when they’ve been achieved.

1. Set up a reward system for things everyone will share if EVERYONE meets their goals. With a team approach to goal-setting, we are no longer toiling in isolated obscurity on tasks that only benefit us. We are working together to achieve group success — at which point we as a group will have something to celebrate. Not only is this motivational for each of us individually, but it also provides a strong incentive for everyone to help and encourage each other to meet their goals. We will decide together what the specific rewards will be, but I’m thinking experiences we share as a family would be good — whether it’s a day trip to the museum or zoo, or a longer weekend trip when we’ve achieved all of our goals for a longer period of time.

2. Celebrate wins, big and small. In the first week or two, while the idea is still fresh, it may be tempting to dismiss short-term wins as too “easy” to really warrant celebration. But by creating a habit of rewarding successes, even small ones, we condition ourselves to relish the victories of everyday life wherever and whenever we find them.

3. Track metrics. Ok, this might be where you decide I’m going too far with applying business tactics to personal life (and it’s ok if you skip this one if you decide to try this yourself). But in my opinion, setting measurable goals and tracking them religiously is the only way to truly know whether you’ve achieved anything. Personally, I’m a lot more likely to feel like I haven’t achieved as much as I’d like, even if I have, than vice versa. But by tracking quantifiable metrics, you can truly know how much (or how little) you’ve accomplished. Especially with things like wellness and self-care, which are otherwise so abstract, setting up a system to track metrics will make your success more tangible and therefore more “real” to you. For daily and weekly tasks like the ones my family will be focusing on this year, a simple monthly checklist is probably sufficient, but for longer-term goals, you might need to be a little more creative in deciding on “key results” that indicate that you’ve achieved your objective.

4. Always be improving. I’ve always thought that a major downfall in New Year’s resolutions (and fad diets) is that once you slip up once, or for a period of time, it’s easy to throw in the towel and declare defeat. The nice thing about an improvement mindset is that it acknowledges that nothing is going to be perfect (or stay perfect) right out of the gate. The goal is to improve over time. So maybe you don’t get everything done perfectly the first few weeks. But if you’re quantifying, you can start to track incremental improvements on a week-over-week or month-over-month basis — and of course, reward yourself for the improvement when you start to see it.

Implementing a new project management system has definitely made me feel more connected with my team at Nanno, and I’m optimistic that it will have the same side effect at home. Rather than feeling like the days slide by leaving half of our daily tasks undone (and wondering whose fault it is), I look forward to helping teach my kids how to set and achieve their goals, by leading by example and by building a “culture” where everyone helps each other succeed.

And if, as a byproduct, I happen to provide my daughters a role model for a mom who devotes a little time and attention every day to her own wellness and self-care, then all the better.