1,000 Days
Have you ever found that when you look back on your life, certain patterns emerge?
I guess that’s why they call hindsight 20/20.
For as long as I can remember, I’ve enjoyed starting things.
In second grade, I wrote and hand-illustrated my first “book,” a tale of a dog and a grand adventure. I’ll never forget the first time I saw that book on the shelf of the Jackson Elementary School library. ❤️
My junior year in college, I co-founded a longboard skateboard company called Pancho Longboard Company. Along with my co-founders Joe and Eric, we turned an idea hatched in a marketing class into a Southern California-based skate and apparel brand. We were always a small operation, but at our peak, we had a manufacturer in British Columbia, and products in skate shops across seven states.
The next stop was taking a job at a marketing agency serving nonprofits called Masterworks, where I would hold seven different roles over 18 years, mostly building or growing teams, including our digital team, experience design team, media team, analytics team, strategy team, and a consulting group we called strategic innovation.
As time went on, I learned that if I were to start and run each team out of my own skills and experience, these wouldn’t be very effective or very good teams.
So I had to learn to lead leaders – people with tremendous talent, drive, experience, and leadership capacity. Leaders like Josh, Mark, Steve, Ray, Amy, Allen, Bryan. To partner with them. To encourage them. To discern with them. They were the real stars, and I got to experience the joy of coming along and building with them.
Looking back, I noticed a pattern every time we started something new. It usually took two to three years to get traction – where what we were doing finally clicked with the mainstream, not just select early adopters.
At first, there was a lot of unknowns, testing and experimenting to see if we were on the right track. Then we’d start to see the shape of things – like, okay, we’ve got something here.
But often it felt like we were speaking a different language than everyone else, and we had to find the words that would resonate.
Finally, sometime around the two-year mark, it felt like the pieces really started to come together – our work clicked, and momentum began to build quickly.
It was like the first two years were experimentation, figuring things out, and building with the early adopters. We could do great work in those early years, really innovative stuff, and grow, but it was always around that 2-3 year mark where it really started to take off.
1,000 Days
Last year, I was talking to my friend Dan Serdahl. Dan works with entrepreneurs and church planters and has significant experience helping leaders start new things. We were having dinner, and I shared this pattern – that it seemed no matter who it was or what the “new thing” was, it seemed around the two year mark, it really started to gain traction.
Dan immediately resonated, sharing that he’s seen a very similar pattern. He had noticed that it took a couple of years, but around the 1,000-day mark, things would start to happen in an accelerating way. They began to see momentum build from the compounding efforts of the past 1,000 days.
I did the quick math = 1,000 days is 2.7 years, or 33 months.
I think Dan’s right. Whether it’s two or three years, it takes time, discipline, experimentation, and building on early wins to compound everything together and see momentum build.
💡 Takeaway: Any new work takes time. Look for promising signs along the way, but recognize that if it’s worth doing, it will take effort and time to bear fruit.
Are you doing a new thing, whether that’s within an organization, or on your own, or even something outside of work?
Where are you in your 1,000-day journey?
I asked Dan what he’s noticed about those 1,000 days. Here’s what he had to say:
1️⃣ It’s a longer runway than you think.
2️⃣ You will remain in “discovery” mode longer than you expect – and you “should” celebrate it.
3️⃣ Not everything is “up and to the right,” aka linear momentum: it’s more often cyclical, PLUS linear.
4️⃣ It’s SUPPOSED to take longer than you think to reach momentum.
First, you are overcoming friction to gain initial traction. Traction is not the goal – velocity is. That’s why an entrepreneur, no matter how successful they may feel (or not!), wisely stays in discovery/discernment mode much longer than one might expect.
Something big happened in my world this week.
1,000 Days of Imago
This week – June 2, 2025 – marked 1,000 days since going all in on Imago Consulting.
When I founded the company, there were some very clear things that I wanted:
💜 To help nonprofits and businesses.
💜 To drive sustainable innovation.
💜 To create health and flourishing, both for me and for those I work with.
💜 To spend half of my time writing, researching, speaking, and…
💜 To spend the other half of my time working with leaders and organizations to help them grow.
But there were a million details. How much of our work would be around fundraising? How much would be about subscriptions and recurring revenue? What exactly would we do to help those organizations grow?
I remember telling people, I felt like I was just starting a game of chess, and I really wanted to know not just what move to make next, but what move I’m going to make six moves from now. If I do this, and then that, what will that lead to, and then what would I do then?
Above: 1,000 days ago – stepping into the unknown. Excited. Anticipatory. So many questions ahead, but at peace.
The past 1,000 days have been a journey. Building. Experimenting. Setting goals. Staying disciplined. Looking ahead, but making one move, one decision, at a time.
And we’re seeing the momentum build.
The Rise of Sustainable Giving launched a few months ago, and more than 10,000 leaders in the first 10 weeks heard the call to build recurring, reliable, and resilient revenue.
The Sustainable Giving Podcast just launched, and in one week, more than 10,000 leaders were introduced to the message of sustainable giving.
The Sustainable Giving Workshop was announced for September 10-12, 2025 – Part workshop. Part summit. Part retreat. ALL experience. (Capacity is already filling up, with the biggest discount expiring on June 15 – learn more and save your seat today.
And perhaps most importantly…
The Sustainable Giving Growth Assessment, our flagship offering and my absolute favorite thing we do, is taking off. The Growth Assessment is a 10-week, 10-part deep dive that results in an action plan for transformation, leading to a strategic roadmap for growing sustainable giving.
Coming alongside charities and helping them create a roadmap for sustainable revenue growth brings me immense joy, and I love seeing leaders discern and implement the strategies that will foster health for their organization.
Can we Help you Grow Sustainable Giving?
The book. The podcast. The workshop. The Growth Assessment.
My favorite way to help, for the right organizations, is our flagship offering, the Sustainable Giving Growth Assessment and Action Plan.
We partner with organizations to dive deep into their specific context, and create a roadmap for cultivating sustainable giving.
The Growth Assessment is the primary way we achieve this.
In the Growth Assessment, we dive into 10 different growth areas – including program design, program growth, and program cultivation. We conclude with a deep dive analysis, breakthrough insights, and concrete recommendations to unlock growth in sustainable giving.
Through interviews with your team, reviewing your current activities, assessing your donor experience, analyzing key metrics and patterns, and understanding the team’s unique strengths, we develop a tailored set of recommendations for measurable results and growth.
If you’d like to explore whether a Sustainable Giving Growth Assessment and Action Plan might be for you, you can learn more here, and contact us if you would like to explore fit.
Your 1,000 Days
Where are you in your current 1,000-day journey?
You might have been in a role longer than 1,000 days, but we’re all involved with newer initiatives or responsibilities – what are those?
I believe we’re all on a 1,000-day journey in some area of our lives.
If you are in your first 1,000 days… some final encouragement for you:
Push through “the dip.” Anything worth doing is going to get hard at some point. Probably really hard. I wrote about the dip, a concept from Seth Godin in The Intersection of Overconfidence and Self-Doubt. If it’s worth doing, it’s worth pushing through.
Develop discipline. Use this time to develop the habits that will serve you for years to come. Keep moving forward, one foot in front of the other.
Give yourself what I call “forcing functions.” Make commitments that force you to step up. For example, when I founded the company, I knew I wanted to write more, so I committed to one article a week, via The Wave Report. You are now reading the 144th consecutive weekly Wave Report. It’s been hard work, but I’m so glad I did.
Get wise counsel. Seek out trusted counsel from multiple sources, and weigh all the advice you get against who you are and what your vision is. “Where there is no guidance, a people falls, but in an abundance of counselors there is safety.” Prov 11:14
Seek to understand yourself and your unique gifts. Every person is unique, and their approach to things should reflect that uniqueness. The better you understand yourself, your gifts, and weaknesses, the better equipped you will be to make decisions that leverage who you are.
🎙️ Bonus: I recently talked about this 1,000-day concept with my friend Taylor Shanklin on her Talking Shizzle podcast. Check it out at “Talking Shizzle: Unlocking the Power of Subscriptions for Business and Charity Success.”
Until next week… Surf’s Up! 🌊
- Dave
About the Author | Dave Raley
Consultant, speaker, and author Dave Raley is the founder of Imago Consulting, a firm that helps nonprofits and businesses who serve nonprofits create profitable growth through sustainable innovation. He’s the author of the book The Rise of Sustainable Giving: How the Subscription Economy is Transforming Recurring Giving, and What Nonprofits Can Do to Benefit. Dave also writes a weekly innovation and leadership column called The Wave Report, and the co-founder of the Purpose & Profit Podcast — a show about the ideas at the intersection of nonprofit causes and for-profit brands. Connect with Dave on LinkedIn.
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