Set your win condition

Align your actions with your win condition to avoid burnout and achieve long-term creative success without freaking out about doing things you like instead of spending every second "being productive".

Hi,

We finished conference season not too long ago, and wow was it sobering to see so many people I love and respect burned out beyond what I thought possible last time I saw them when they were already burned out beyond what I thought possible.

The exhaustion wasn’t just physical; it was emotional. We’re talking about the kind of burnout that comes from chasing a goal you’re not even sure you want anymore. Worse, it comes from never really wanting it in the first place.

Don’t get me wrong, we all wanted to be entrepreneurs, maybe even influencers, but did any of us really want to own a media empire that pulled at our every last nerve every waking hour of the day (and plenty of our sleeping ones, too)?

It feels like we’re cast adrift on an ocean we never signed up to sail and now the only choice is to navigate the choppy waters and find land before we either drown or die of dehydration.

Too many of us are following a plan that doesn’t align with the success we actually crave because we never even knew we had to plan for a thing that hadn’t even been invented yet.

Burnout is almost a given at conferences, but this year there was a deeper issue. I talked to so many people who had been grinding for a long time, expecting that at some point it would get easier, only for the opposite to happen Many of them had a plan, but their win condition was either undefined or at odds with that plan.

I’m definitely not immune from this kind of things. In fact, I feel like I’m acutely aware of noticing this in other people because I’ve been through it multiple times recently.

It wasn’t easy, and it still isn’t. When people asked how we planned to make money, we shrugged. The truth was, we didn’t know. We just hoped it would work out. Looking back, had we been a little more strategic at the beginning and projected forward to our win condition, we might have avoided this whole mess entirely.

What is a win condition?

A win condition is the ultimate goal that makes all your hard work worth it. It’s not necessarily about hitting specific revenue targets or achieving fame.

It’s about what makes you feel fulfilled in your work.

This is such a powerful exercise because it cuts through all the noise and settles on how winning feels to you. It probably has nothing to do with having a million followers, either. It’s probably about having the security to live your best life.

Nobody’s best life is lifestreaming their every thought to their followers, not even the Kardashians. Sometimes, you just wanna have a think and a poo in peace.

One major key to finding happiness in your business is to pick a win condition that’s aligned with what you truly want, not what the industry or society says success should look like. Many people make the mistake of setting a win condition based on external validation, like money or fame, when their real desire might be more personal, like more time with family or space to pursue their creativity.

Once you have your win condition, you can work backwards to the platform, audience, and assets that help you get there. Then, you can work forward to find the actions that can best help you get to your win condition without betraying your values.

If you haven’t ever thought about this before now, trust me you’re not alone. I talk to creators all the time who’ve planned and prioritized their whole adult life who have never set a win condition for their career.

My personal win condition looks a lot like my life now. I want to be able to take any weird idea in my head and find enough people excited to make it happen that it will make me money. I want to do very few things, and have my whole day free to dicker around with people that inspire me, without having to worry about the money piece of it all because there is always more than enough and its growing all the time.

I’ve slowly been able to expand doing that kind of thing from a mere 10% of the time a decade ago to 60% of the time these days, but it wouldn’t have been possible if I couldn’t visualize my win condition.

When your win condition doesn’t match your actions, you’re setting yourself up for burnout and frustration. You might feel like you’re constantly hustling but never getting closer to what you really want. Worse, if you don’t know your win condition, you could create a plan at odds with what you really want out of life, which is my nightmare situation.

After talking with thousands of creatives in my career, I think that they mainly have a KPI misalignment issue. There are hundreds, maybe thousands of different data points that we can track in our business at any time. Tracking any one of them closely will send us tumbling off in a different direction. While these raw data points track various aspects of our business (like website visits, email opens, or social media followers), KPIs are carefully chosen to align directly with what matters most to success.

KPIs are specifically chosen to highlight performance in areas that most critically impact success, ensuring clarity and alignment across the team. Tracking too many metrics can lead to information overload, but carefully selecting a few KPIs allows organizations to focus on what matters, make actionable decisions, and efficiently monitor progress without being distracted by less relevant data.

Most business track no more than 3-5 KPIs at any one time, and reevaluate every quarter.

Creators often struggle with defining the right KPIs because we’re not just businesses; we’re people, too. People often have different needs and desires than businesses, so it’s hard to parse which ones really align with our wants and needs.

This leads to creators either tracking the wrong things because somebody told them what was important to them and it sounded nice, or getting overwhelmed and tracking nothing then wondering why they aren’t getting anywhere.

If that sounds like your life, then you’re not alone. Many creators track the wrong KPIs, focusing on metrics that don’t align with their win condition. It’s not that they aren’t productive. They’re measuring the wrong things.

The key to sustainable success is aligning your KPIs with your win condition. For me, I’ve had three KPIs that worked for years:

1. Quality conversations had in a week: I aimed for 10 meaningful interactions where something valuable was exchanged.

2. People added to my mailing list every month: Since I launched a lot, I needed to constantly refresh my prospects so I could keep growing.

3. Projects finished in a year: As long as I was completing projects, I wasn’t too concerned about income goals, but if I finished something, I knew it would be okay.

These KPIs worked because they aligned with what I actually wanted to achieve. I knew that if I had good conversations and kept finishing projects, the money would follow.

Defining your win condition

Realigning your actions with your win condition isn’t easy by any stretch. You may find that old habits die hard or that you’re tempted to revert back to traditional measures of success. The key is to stay focused on your true goal. Don’t be discouraged if it doesn’t happen overnight.

Winning is kind of like meditation. We all know that it’s impossible to clear your mind for long, but the process is the point. It’s okay to take small steps toward realignment, and it’s normal for the process to take time.

Some may fear that shifting their KPIs could hurt their business in the short term. For example, if you stop obsessing over sales and start focusing on conversations with customers, you may initially see a dip in revenue. But over time, this realignment can create a more sustainable business model that’s rooted in the things you actually care about.

If you’re feeling burnt out or like your work isn’t moving you toward success, it’s time to reflect on your win condition. Here are some steps to help realign your actions with your true goals:

1. Reflect on your most rewarding experiences: Think back to moments in your life where you felt a deep sense of accomplishment or fulfillment. What were you doing? Why did it matter to you? These moments often reveal your real win condition. For example, if you felt most alive while traveling or mentoring others, your win condition might be more about freedom or impact than financial success.

2. List what you truly enjoy doing: Write down the activities that bring you joy, even during challenging times. These are the things that energize you, rather than drain you. If you consistently find joy in brainstorming with others, or spending time outdoors, those activities are likely more aligned with your win condition than, say, endless hours of marketing.

3. Set KPIs that align with your win condition: Once you know what’s most important to you, set 3-5 KPIs that reflect that. If family time is your win condition, track hours spent with loved ones, not just projects completed. If creating a community is your goal, measure quality conversations instead of just sales. Aligning your metrics with your values helps reduce the cognitive dissonance that leads to burnout.

It’s easy to get caught up in what the industry says your KPIs should be, whether that’s sales, social media followers, or revenue. ON top of that, it’s very easy for external pressure to push you further away from your win condition, especially if you don’t have one. The challenge is to resist these external markers of success and focus on the internal metrics that matter most to you. Your journey may not look like anyone else’s, and that’s okay. In fact, it should be different.

Picking your hard

It’s also important to recognize that sometimes your short-term actions might not fully align with your win condition, especially if you have immediate financial or professional obligations. As I said above, I only get it right about 60% of the time and I’ve been deep in it for a long time.

I’ve done lots of things that didn’t align with my win condition for years in an effort to get where I could move toward my win condition with better alignment. The goal is to ensure that the majority of your efforts align with your long-term vision as often as possible.

For example, you may take on projects that pay the bills even if they don’t perfectly align with your win condition. That’s okay, as long as those projects don’t steer you too far away from what you ultimately want for too long. Just make sure you’re always moving toward your win condition, even if it’s in small, incremental steps.

Every path is hard. The universe is full of hard choices, and it’s up to you to pick the ones that align with what you truly want. For Monica and me, that meant choosing the hard work of building a community and shipping. We could have chosen the hard of running a coaching business, but it wasn’t the hard we wanted.

If you pick a hard that aligns with your win condition, the challenges will still be tough, but they’ll be worth it. When the hard you pick leads you toward something meaningful, it makes the struggle more bearable.

If you’re feeling burnt out or unproductive, I suggest rethinking what productivity means to you. Blow up everything you think about success and productivity, and focus on the 3-5 things that you actually:

1. Like doing: Think about what activities bring you joy. This is about finding the work that excites you, even when it’s hard. What do you enjoy enough to keep going when things get tough?

2. Do consistently: The key to success is consistency, but not in the way you might think. It’s not about forcing yourself to grind every day; it’s about finding the things you naturally do consistently. These are often the activities that don’t feel like work because they align with who you are. If you’re always finding time to garden, walk, or brainstorm with a friend, those might be the things that drive your success more than any productivity hack.

3. Really make you feel successful: Success is personal. It’s not just about hitting big milestones or revenue goals. Instead, focus on what makes you feel accomplished on a daily or weekly basis. The key is to find the metrics that make you feel like you’re winning, even if they don’t match up with traditional notions of success.

It could be “birds watched in a day” or “hours strolled through town” or literally anything. That is not a success issue. It’s a KPI misalignment issue, and it’s driving us all crazy right now.

We spend so much time “prioritizing” and “setting intentions”, but have you ever sat down and thought about your win condition? What is this all for? Is it for freedom? For prestige? For money?

What does it even look like when you wake up after getting “everything you always wanted”? The reason people are almost unanimously disappointed when they “win” is because they realize their intention was misaligned with their reality.

Take a second to think about what “winning” feels like and how you move through the world once you get everything you want. Then, really look at your priorities and ask “Are these things really going to get me to that win condition?”

Either way you will suffer for what you love. Life is little more than choosing your hard, but often it’s possible to pull forward bits of our win condition over time.

I’ve been semi-retired for years because I realized my win condition was about freedom, and the ability to explore whatever I wanted whenever I wanted, and largely, I already had that.

I don’t want to retire. I want to (mostly) do whatever I want whenever I want to do it. Ten years ago that kind of thing only happened on weekend, and then when I started my business for years it only happened never. Instead of doing what I wanted, I was stuck going to shows every weekend, and then hammering out projects during the week.

By the time the pandemic came, I was pretty good about doing whatever I wanted for half the week, but the other half would be filled with shows.

After the pandemic, when shows stopped being important to my business, I had developed the structures so I had could do mostly what I wanted,

Since I enjoyed the work, it wasn’t much of a struggle for me to do it, but that still wasn’t much freedom. I still had to write, and then launch/pack books.

After getting saddled with long COVID, I’ve not been able to do that much, so now I have fulfillment houses that mainly pack my books, and I do very, very light launches mostly contained to my email list.

I have a lot of financial obligations that I’m on the hook for, but by and large I nailed it.I don’t have many meetings during the week, unless it’s with somebody I want to talk to, and there’s only about 5-10 hours of work a week I’m forced to do.

Some of that is because I physically can’t do shows anymore and doing more than 1-2 hours of work is exhausting. Much of it is because I like to be able to go see a movie and disassociate for long periods of time. I read a book or two every day, and many interesting articles, which is a neat way to spend my time.

Most days, the biggest hinderance to me doing what I want is taking a shower.

This is my win condition. I have some money in the bank to help with any emergencies, am working on projects I love with people I love, and I have few obligations weighing me down.

I was sold a bill of goods about being an entrepreneur, and I feel like I finally made good on it. I can still only do it 60%-80% of the time or so (thus the semi) part, and I can’t just stop right now, but my retirement will look mostly like what I do now. So, I’ve already won.

Aligning your actions with your win condition is the key to avoiding burnout and finding long-term creative fulfillment. It’s not just about the hustle. It’s about identifying the goals that truly matter to you and measuring success on your terms. Pick the right hard, track what truly matters, and create a life where your daily efforts move you closer to the success you truly want.

What do you think?

• What’s one area of your career or life where you feel your KPIs might be misaligned with your true win condition?

• How do you define success for yourself, and how has that changed over time?

• What “hard” are you currently facing, and do you feel it’s aligned with the win condition you truly want?

Let us know in the comments.