Tracking Improvement in a Creative Profession

4 min readOct 20, 2021


How do you know that you’re improving? We discussed this question with a group of entrepreneurs and corporate innovation professionals during a recent roundtable that I host about all thing’s innovation. We had a fascinating and illuminating discussion, so I wanted to capture some of it in a post to share with a broader group.

I qualified the question by saying that commercial success can’t be used as the only measure of improvement. The essence then became how does an entrepreneur, creator, or innovation leader know whether they are getting better at their craft? Many professions have accreditations and ongoing required education that signify how much you know about a professional craft, and whether you are continuing to grow your knowledge about the craft. The accreditations and certifications qualify how much someone knows about their profession, and as a result provide a gauge for everyone else in the world. Professionals in many areas even have letters after their name representing their level of knowledge and experience about their craft.

Entrepreneurs, creators, and innovators don’t have the same structured education and professional accreditation and certification thresholds that other professions do. The determiner of most professional prowess and capability is how well someone knows and executes their craft. Does an architect design appealing, sustainable, and functional buildings? Does an accountant conduct proper accounting practices and principles? Does a lawyer provide sound legal advice and direction? Being great at a craft for these professionals and getting better at it over time is paramount to their success and fulfillment. But how does someone who is in a very creative, fluid, and often fraught with failure profession know whether they are good at the skills of their craft and are getting better over time?

The roundtable discussion started with most people having quizzical looks on their faces and saying things like “I’ve never thought about this before” and “I don’t know how I would determine whether I am improving or not.” As the discussion continued, we started to unpack some of the layers as to how entrepreneurs, creators, and innovators can determine if they are indeed getting better at their craft.

Here are some of the themes that started to resonate:

  • Purpose: It is critical for creators and innovators to understand what drives and motivates them. It isn’t probably the same things that drive and motivate people in other professions. Understanding why you have chosen to be a creator of some sort is the first step in knowing why you are doing it and how you then might be able to measure whether you are getting better over time.
  • Clarity: This is likely a result of purpose. The group ended up with a consensus that one of the ways to know if you are getting better in such a loosely defined craft of entrepreneurship and innovation is clarity. What previously seemed out of reach, blurry, or practically impossible now seems clearer and closer. The clarity comes from the relentless pursuit of a problem and an appropriate solution with a ton of experimentation along the way. Much like an investigator or scientist will use process of elimination to gain clarity, so do entrepreneurs and innovators.
  • Confidence: Continuing the cascade affect, confidence is an outcome of greater clarity. When a problem becomes clearer, so too does the solution, and we become more confident. Entrepreneurs and innovators almost always start out with a lack of confidence, because things are so uncertain around what they are trying to do. Confidence at the early stages of a new entrepreneurial or innovative endeavor is often hollow confidence because not much is known or figured out yet. But as clarity increases, confidence increases.
  • Decision making: Faster and better decision making is where we ultimately ended up with the discussion. Improved decision making was the most impactful way of identifying whether an entrepreneur or innovator was getting better at their craft. Good decision making is a result of the above measures and is also representative of someone’s skills and expertise getting better. The speed at which entrepreneurs and innovators can learn, take in new information, and make decisions is paramount to being successful. Decision making is a skill just like any other skill, and the ability to make decisions quickly is imperative to entrepreneurs and innovators.

These are some of the areas that our group captured as a snapshot into how entrepreneurs, creators, and innovators can determine if they are improving at their craft. I’m sure we overlooked several more during our limited time together. What are other ways to track whether someone in a fluid and multi-dimensional profession like entrepreneurship or innovation can know if they are actually getting better? Let us know your thoughts with a comment.

-Ryan Frederick, Principal at AWH. We are helping companies fuel growth through technology.




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