I'm wrapping up this post at the San Francisco Airport, where I'm headed to Bangkok for the rest of the year. And as I wait to board, I'm thinking about how there's always another level.
I was speaking with a client recently who had just made a major career shift—he left a high-paying manager position at a respected Series E startup to launch his own agency. In the first few months, he's already signed over $150,000 in new business.
By any measure, this was a huge success. But he described himself as being "in a lull". What did he mean?
None of his new clients had yet used his work in a way that demonstrated his prowess as a marketer and advisor. He craved a testimonial, a “big win” he could point to.
This sense of dissatisfaction is common among the high-achieving founders and leaders I work with. They have incredibly high standards for themselves, which serves them well in building great companies and products. But it also means they sometimes struggle to celebrate incremental wins along the way.
There's always going to be the next goalpost to reach, the next challenge to tackle. As soon as we achieve one milestone, our mind instantly jumps to the next one. I see this in myself too - as I've made the leap to coaching full-time, I'm checking off important steps like announcing the end of my sabbatical, recording a bunch of podcasts, and finishing my book on pivots.
But of course, now my mind is on the next goal - signing my first few clients, refining a my unique coaching methodology, onboarding support team members.
The reality is, we need to take time to acknowledge and appreciate the progress we've made. Each small step builds the foundation for eventual success. Not every win needs to be an IPO or a record-breaking launch or a big pay day. Sometimes it's just finding your next client, shipping a great feature, or fixing a long-standing problem.
You need to stay hungry and push towards those big goals, but taking an incremental win along the way keeps you fed and energized to do more.
Here are a few ways I recommend celebrating progress and giving ourselves credit:
- Verbalize wins, even small ones, to others - this makes them feel more real. Call a friend or family member and share good news.
- Take time to reflect on how far you've come. Read old journal entries, look back at early work samples, remember where you started.
- Savor the win, don't just check the box. Go out for a nice dinner, take a short trip, buy yourself something meaningful. Take a moment to appreciate the good feelings.
- Document and publicize these milestones for your team or even on social media if that's your style. Positive reinforcement helps solidify achievements.
- Share credit with your team, family, and supporters. Recognize you didn't do it alone and spread the love—their appreciation will make your win feel better.
- Keep perspective by reflecting on people who achieved success later in life. You're still early in your journey. There's still time.
Life is a long game, with many challenges still to come. But progress depends on celebrating the milestones along the way. When we take time to appreciate our incremental wins, we build energy, motivation and resilience for the long haul.
Keep swinging big.
—Jason
