Charting a Future through Past Lessons

“You can’t connect the dots looking forward, you can only connect them looking backwards.” - Steve Jobs


It’s easy to feel excited for a fresh start to a new year. A clean slate with the best intentions to work hard, but in the midst of thinking about what the future potentially holds, it’s important to reflect upon both the good and bad experiences. This week, we explore the importance of looking back to propel you and your team into the future.

As we come to the end of another year, it’s important to reflect on the good and bad experiences so you can analyze what’s working and where there are opportunities to make some adjustments or improvements.

The ending of one year and the beginning of another offers a natural opportunity to take some time to consider the bigger picture. Good Leaders highlight past accomplishments as a way of building collective confidence about the future.

The study, published in the journal Memory, found that those who reflected on their problem-solving achievements and moments that defined their identity gained higher self-esteem, self-efficacy, and a general sense of meaning in life. 

In today’s fast-paced business environment, we breathlessly race ahead before the dust settles, driven by the desire to move full steam ahead. However, leaders who cultivate a clear historical perspective move further and more effectively into the future than those who don’t.

Winston Churchill believed that “the longer you can look back, the farther you can look forward.” 

Four Ways to extend the horizon for you and those you lead:

  1. Reflect on the Past Year: Reflecting on the past allows you to see how far you’ve come and all that you and others have achieved. Explore the following:

    • What are the things you achieved

    • What were the obstacles experienced and how did you overcome them

    • Use failures as lessons learned to build plans for future success

    • Reflection reduces the risk of repeating mistakes or not recognizing improvement opportunities

    • Provides an opportunity to see a new pathway for success, galvanizing future efforts. 

  2. Evaluate the Present: It is critical for leaders to evaluate the present and understand that this practice will guide their planning for the future:

    • Ignite passion and purpose in all accomplishments

    • Look for lessons learned during times of struggle

    • Critique choices made and the subsequent outcomes - what went well? What requires change?

  3. Link the Past and the Future: As you look at the past and present, you can now begin to connect those learnings to the future:

    • Highlight past roles and the values that defined them 

    • Inspire others to see their value and role in the future

    • Where might you be holding back from embracing a future vision

    • Where might you have fears that are holding you back

  4. Prepare for the coming year(s): It’s not time to look to the future:

    • Make time to plan and prepare for the future

    • Prioritize how you will become a better version of yourself

    • Identify the next achievements you want to make 

    • Set goals to give as a way to create a focus for the future 

    • Evaluate what you will need to make those goals a reality 

    • Prepare and plan for the challenges that may show up and how you will manage these

Importance of Reflection: Leadership is the ability to convince, motivate, and lead people to achieve a common goal and attain success. Reflection helps us know where we are going, what progress has been made, and what is needed to get across the finish line.  

So, how can you begin to build your process of reflection:

  1. Calendar time for Deep Reflection

  2. Keep an Accomplishment List throughout the year

  3. Meet with others (team, leaders, etc.) and discuss learnings, share insights, and plan for the future

“Becoming a leader is synonymous with becoming yourself.” - Warren Bennis

As you close out this year to begin a new one, remember:

  • You can go farther than you first believed by recognizing the achievements of the past.

  • You can gain commitment to the future by honoring the past.

  • You can reduce fear of the future by linking the past to the future.

  • You can find your future value proposition by exploring the past leaders’ real contributions, not merely their legends.

Wisdom is looking back at your Life and realizing that every single event, person, place and idea was part of the perfected experience you needed to build your dream. Not one was a mistake.
— John Federick Demartini

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HBR’s “On Managing Yourself”

This month's must-read for leaders is a compilation of vital Harvard Business Review articles focused on self-management. The book emphasizes the importance of self-reflection, urging professionals to recognize their core strengths and values as the bedrock of success. Designed to maintain engagement and productivity throughout one's career, it's an invaluable guide for leaders seeking sustained personal and professional growth

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Self-Awareness: The Hidden Key to Leadership Excellence