Want to Make 2019 Your Best Year Yet? Stop “Should-ing” on Yourself!

Last week, I had the privilege of launching the second Arts Agency Capacity Building Consulting and Coaching Program & Mastermind.

Funded by the city of San Antonio’s extraordinary Department of Arts and Culture, this unique, high-touch program brings together Executive Directors and Board Presidents from a wide variety of organizations to leverage their unique impact in order to increase revenues, stakeholder engagement and overall capacity; creating the possibility to transform their organizations (and themselves as leaders) as they learn from and support each other over the course of six months.

As a result of the the sheer volume of coaching sessions I facilitated, I quickly began to see some patterns emerge. One such pattern reminded me of a dynamic I often bring to light to help clients get unstuck and move forward.

Do you ever say or think:

“I know I should….______, but I’m just…_____”

Here are some examples:

  • “I know as the board president I should be out talking with my corporate clients, but I just haven’t done it yet.”
  • “I know I should be more confident as a leader, but I just can’t seem to find my way.”
  • “I know I should spend more time with my family, but I just have so much work to do.”

Anytime you hear yourself saying (or thinking) the word “should,” I invite you to take a minute to actively assess what’s going on.

Write down the answers to the following questions:

  • What do I believe I “should” be doing?
  • Why do I believe this? (List all the reasons.)
  • Why have I not been doing it?  (List ALL the reasons, whether they are external forces or the internal thoughts, fears, limiting beliefs you observe. Write them ALL down.)
  • What do you notice?  What if some of your assumptions and fears don’t have to be true?

It may help to imagine you are helping someone else through this issue, perhaps someone on your team, or a close friend.

  • What do you notice? What would you say?

Once you gather this intel on yourself, you’ll be much better equipped to know how to address it, rather than continually beating yourself up!

During my visit to San Antonio, it was interesting that in many cases, the instincts for not taking action were actually appropriate – we just needed to find the key to unlock the actions that do need to be taken.

Here’s what we found through our coaching sessions:

  • In the case of the Board President who wasn’t going out and asking individuals and corporate sponsors for donations, it turns out that the organization was still in the process of cleaning up their financials, and they didn’t (yet) have a solid picture to convey.  Therefore, they realized there was no way that they could go to their contacts with integrity to make an ask. Instead of being hard on themselves, the focus has now shifted to get the budget and year to date finalized this month. And then, I guarantee, they will be able to communicate where the need is to prospective donors.
  • The leader who observed themselves being hesitant, realized that they felt somewhat disconnected from the long-established organizational language. Instead, new language was created that resonates with her unique purpose, beliefs and passion.  The organization’s mission remains the same. The leader removed their limiting belief, found value in their own voice and their unique “why” – and “all of a sudden” knows the path forward and will be able to show up authentically and connect with stakeholders.
  • The multiple leaders who yearned for more time with their families and believed that they had no choice, identified multiple internal fears and assumptions that they would not be viewed as committed or professional if they left work before the job was done. (We also tested the assumption that an increased number of hours automatically equates to results and impact!) Because each organization had their Executive Directors, Board Presidents and often other key stakeholders in the room, they were able to re-establish priorities and deadlines – as well as agree on how each could contribute to them.  Often, this pattern requires a combination of coaching (to address mindset and limiting beliefs) and consulting (to create action plans and roles and responsibilities that relate to realities of current capacity).

Over the next two weeks as you reflect back on 2018 and envision the kind of life you want to create in 2019, go easy on yourself.

Don’t “should” on yourself!  

Instead, I encourage you to observe, test your assumptions, value yourself, curate a path forward and ask for help.

To your success,


If you would like to curate your path forward and make 2019 all that you envision, please make sure you a part of my e-community – I’m launching an exciting new program in the new year.   And, as of Dec 14, 2019 I have one spot remaining for a senior leader in my 6-month VIP Leadership Coaching & Mastermind – we begin this month. Schedule a confidential call with me today.

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