To-Do or Not To-Do, That is the question

A few months ago, I made the decision to be better and to do so publicly. I realized that it had been years since a similar effort led to me writing for publications. And in my regular practice of speaking with others about their aspirations I was reminded that perhaps I needed to revisit my own. As I decided to commit to improvement, I began by asking myself four question: 

cant to can

  1. What are all the areas where I could improve?
  2. What am I prepared to dedicate to improving?
  3. What would I need to most confidently pursue improvement?
  4. What is the metric I will use to measure whether I’ve been successful?

Those who have known me for a while won’t be surprised by the fact that I had to start with a set of questions that led to data points that would measure the results. I’m a creature of some pretty repetitious habits. They work for me much of the time–and I believe they help others. 

What are all the areas where I could improve?

What I considered: I don’t think I’m being self-critical when I say I have loads of work to do on myself. Don’t we all? I considered possible areas of improvement that ran the gamut from improving my fitness and financial health to my fashion choices and cooking. There was a litany of possibilities all of which were worthy and each of which could have improved my life in some way. 

What I did (and why): I decided to tackle my fear and loathing of being on video. When I think about how I can best model behavior for others I wanted to emphasize that at any age we can make an improvement. It was also important to me to tackle something with professional implications that I know is shared by many others. I’ve recognized for some time that discomfort meant that I was ignoring one particularly useful way to reach and support others. So, dealing with the camera whether your presence on video with your peers or in creating content on your own was what stood out for me.

What am I prepared to dedicate to improving?

What I considered: No matter the change we want to make there are important decisions to be made about the time we will set aside, the financial resources we might allocate and perhaps the social capitol we are willing to use or emotional toil we are prepared to weather. Some change is easy, but the stuff that is tied to how we see ourselves, in particular some of our less positive self-perceptions can be a bit of a slog. Understanding what you will set aside to accomplish a task makes a big difference. For example, if I decided that my goal was to run a half marathon I would need to set aside time each day to build up my endurance, money for footwear and food, perhaps a running coach to help my develop a plan and maybe even tickets to a destination half-marathon location.

What I did: I was very fortunate to be on the road where I was able to catch-up with someone I hadn’t seen in years. Ryan is the founder of BetterOn which helps people work on their executive presence. As I spoke with him, I became more confident that his way of working and supporting others could help me. He was smart, funny and deeply empathetic. I knew he had the skills and I would enjoy getting help from him. He was the right person to take me on this journey. I could commit several hours each week to doing homework, speaking with him about

how it was going and recording my progress.

What would I need to most confidently pursue improvement?

What I considered: I’m amazing at creating structure and accountability for things related to my work or hobbies. I am much adept in other areas of my life. For the hardest things I require external support. I love being on a team with someone working towards a common goal. So, I needed to be in sync with a teammate. 

What I did: Ryan and I planned out a schedule for the six weeks where he could review my homework and we could meet and discuss what I had done on the online platform and how I was feeling as result. I knew that the cadence would help me build some habits and instill confidence.

What is the metric I will use to measure whether I’ve been successful?

What I considered: At the time I was really thinking about completing the course. My promise was to do this work and prove to myself that I could be better. That we all could decide to be better at any time.

What I did: About half-way through the process I began to gain a bit of confidence and to see goals differently. IF I gained comfort and understanding in video, how could I have an impact in ways that reached people beyond my writing. I started to think about the kind of stories I could tell or situations I might share that would have a greater impact via video. Moreover, I need to create goals that would lead me to regularly posting videos on a schedule. Having to write for the Post means I need to keep up my writing practice. Is there something like that which can do the same for video production?

So, I started thinking about solo ideas and a video series that I could create, I considered the tools I would need to do them well (ie. the lighting, the recording space or a better microphone) and the cadence of publishing (ie. every three weeks) and the possibility of recording with someone as an accountability partner. I’ve also gotten feedback from Ryan and shared with a few close friends to get their reactions to my ideas.   

While I am much more confident now than I was when I started I understand that continued progress can’t be taken for granted. I’ve failed at sustaining change before and failure will no doubt always be a part of my life. That’s risk is inherent in the goal of being better. Nonetheless, this is preferable to not believing that you can improve.

So, here I stand in this middle space unsure of how this will resolve. Nonetheless, I appreciate the journey and the choice to-do.  I hope that you too decide to take on the to-do of your choosing.

Russ Finkelstein [] is the opposite of your High School Guidance Counselor.  A career coach, social entrepreneur, and advisor to founders, he is currently the Director of Coaching with the Roddenberry Fellowship and a Coach-in-Residence with StartingBloc Fellowship. He was a founder of the noted careers website and was chosen as a Generation Z & LBBTQ Influencer by LinkedIn.


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