Our Backwards Approach to Setting Goals for 2020

to Setting Goals for 2020
26th, 2019
Keyhole - Digital Marketing Agency - Joe Dudeck
Joe Dudeck
President + Founder
Setting Goals for 2020 in Buena Vista, Colorado

The week before Thanksgiving, I took a 24-hour personal retreat to a tiny house in Buena Vista, Colorado — about 2 hours west of my home in Colorado Springs — to get further up into the mountains, clear my head, and set goals for 2020.

My Tiny House Away From Colorado Springs

But if you’ve spent any time listening to Season 1 of our Metaphorically Speaking podcast, you know this is not an annual pilgrimage for me. Goal setting has never been my thing. And it wasn’t until this recent trip that I realized why that has been the case for most of my career and the past seven years of running this business. It’s because I hate failing. I hate not accomplishing everything I set out to do. I hate not being perfect. And so, rather than run the risk of failing, it’s been better (or safer) to never spend time defining clear intentions for myself or the business.

But lately (thanks to my podcast co-host, Shannon Jirik), I’ve realized that safety zone brings about its own set of challenges — chiefly the wasted expense of energy running in place. Without taking time to look at where I’ve come from or where I’m going, I end up spending most of my time looking down — watching my feet move without taking me anywhere.

Not that I haven’t had success.

The fact that I’ve kept this business running for the past seven years means I’ve been successful in beating the national average — with a third of new businesses exiting within their first two years, and half exiting within their first five years. And so, the stats alone tell me that I haven’t stood still that whole time. I know I’ve shifted and moved with the times to not only make some money, but also partner with great clients and people along the way.

The problem, though, is that I can’t look back or forward and easily find the mile markers. I can’t clearly see the things that I did — or the things that happened to me — that caused me to change my business over the years. Nor can I quickly identify the visions I’ve had — or continue to have — for the future of Keyhole Marketing.

But I’m tired of that. And so, with Shannon’s encouragement, I created some new history this year and finally set 2020 goals for the business.

But here’s the thing. I didn’t write them from my perspective today, projecting out to what I hope to accomplish. Rather, I wrote them as I stood, or sat, or drank from December 31, 2020 — looking back on all I’d accomplished and all it took to get there.

And specifically, I asked myself the following 33 questions:

Setting 2020 Goals in Buena Vista, Colorado - Journal Entry


  1. How did I make time and space to nurture myself in order to put my best self forward for Keyhole Marketing?
  2. What work responsibilities or clients provided me the most stress in 2019 and what efforts did I take to ensure this stress remained healthy?
  3. What was I afraid of going into in 2020 and how did I verbalize/share those fears in my community — rather than internalize them?
  4. Who mentored me personally or professionally in 2020?


  1. After sensing any gaps or lack of purpose in my work in 2019 and identifying their sources, what did I alter in order to see change happen?
  2. What partnerships did I pursue to expand Keyhole Marketing’s reach?
  3. What long-term goal did I finally start making progress toward in 2020?
  4. What new applications or tools did I research, consider, and implement to better our efficiency, organization, collaboration, etc.?


  1. How many new clients do I hope to, and actually, serve in 2020?
  2. What industries or segments did these clients come from?
  3. What measures did I take to connect with these ideal clients?
  4. What exchanges of service were fruitful?
  5. Any clients I phased out in 2020?
  6. What conversations did I have with certain clients to reestablish boundaries or expectations?


  1. How did I rate our social media presence going into 2020?
  2. What platforms required more attention?
  3. What did I do more of or do less of on social media this past year?
  4. What type of new content did I develop in 2020?
  5. What did I determine mattered most to us on social media this past year — Number of followers? Types of followers? Engagement rates? Consistent stream of content? Other?)


  1. Other than revenues or client rosters, how did we measure Keyhole Marketing’s success?
  2. What social media goals did we determine?
  3. What email metrics did we set?
  4. What website analytics did we track?
  5. How did we encourage more Google reviews?
  6. What data needed to be considered that wasn’t previously a priority?


  1. What did I see my team looking like in 2020?
  2. Did I hire new talent and for what purpose?
  3. How did the roles and responsibilities of our contractors evolve and remain the same?
  4. What did I delegate to pursue other priorities?
  5. How did my time management change in 2020?


  1. What events and professional development opportunities did I attend in 2020?
  2. Were they local or out of state?
  3. What travel limits did I set for myself in 2020?

From there, I built out my objectives and key results, or as Google likes to call them: OKRs.

What are those? You can find out more than you’d likely want to know via this google video, but, in short, it’s a simple way of creating 3-5 desired outcomes that you want (objectives). This usually comes about by asking yourself:  where do I want to go? — or as I did:  where did I already go? And then by listing out corresponding measurable ways you can know if you’re on track to reach them (key results) by asking yourself:  how will I know if I’m getting there?

And want to know the beauty of OKRs? You don’t want to ever fully reach them! In fact, you’ll ideally only achieve 70 percent of your OKRs. Getting 100 percent means your OKRs aren’t ambitious enough. And that’s music to this perfectionist’s ears!

Clearly, I’m not the authority on setting goals, and so I can’t speak with any certainty on how successful my plan will be. But I’m still going to celebrate the fact that I even have a plan going into 2020!

If you’re interested in setting your goals for 2020 in the same way I did, please reach out. I’d love to connect with you and spur each other on throughout the year.

Happy New Year to us!

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