Many legacy leaders stay stuck because they are trying to figure it all out before they take any action or move forward on a project or goal. They are waiting for clarity to avoid surprises or upsets in the event things don’t work out. And they are trying to avoid a similar mistake or failure that they’ve experienced in the past.
However, you can never figure everything out in advance because life, people, projects, and circumstances will always change.
Overthinking and analyzing becomes a stall tactic and are not effective strategies.
What Gets in the Way:
- Fear of _____ (you fill in the blank)
- Uncertainty of what will happen
- Lack of confidence in your ability to handle changes
- Obstacles that seem insurmountable
- Overthinking or overanalyzing
- Not forgiving yourself
- Failing to learn from past mistakes or failures
- Unable to adjust plan without changing the goal
5 Key Tips to Stop Waiting and Begin
- Embrace Uncertainty. Many legacy leaders do not have a good relationship with uncertainty. They feel that at age 55+ they should already have life handled and figured out. They believe that any uncertainty is their gut or intuition telling them not to do something. The truth is fear comes in many disguises that keeps you stuck and prevent you from moving forward. Journal your fears and concerns. Listen to podcasts. Now, “try out” something new and different.
- Shrink Your Focus to Today and Tomorrow. Big thinkers get themselves in trouble when getting started and even more trouble while staying in action. They overthink, make things too complicated, and fail to understand or address the details effectively. Progress happens when you focus on the small steps required today and tomorrow.
Example, you want to move to live closer to your adult children. However, you may have income, health, or employability challenges (e.g., type of work you will accept) that prevent you from making the move. Begin by working with a career coach, conducting effective networking, and having a resume that showcases your results (See Get Your Brag On! OR The Secret to Winning the Job: Start Bragging).
- Create Deliberate Intention. Deliberate intention is choosing what matters right now and acting on it. Too often, we get in our own way by overthinking and analyzing challenges that may never occur.
- First, declare you will honor your commitment and intention to do so.
- Second, create the goal and intention. (Remember, 10 words or less.)
- Third, ask for help by building a team to support you.
- Fourth, stay focused on the goal and actions required.
- Fifth, celebrate each win. (Get Your Brag On!)
- Finally, don’t forget to acknowledge the lessons learned.
Example, when a man was forced to quit his job due to health issues, it created a financial hardship. By asking for help, he was able to increase his income (pension, SS, and other benefits). But the problem was, his pie-in-the-sky mindset kept getting in his way of moving forward. He believed he had more money to spend than he did, and allowed his vision of what must happen to keep him stuck. By working with a financial coach, he was able to get his thinking in line with his income.
- Focus on One Area of Your Life at a Time. People often freeze because one part of their life lacks clarity or there are issues to resolve. They believe that if they can “fix” that one area, all the other areas will magically fall into place. It’s a comforting false belief. For example, refusing to take a great job opportunity because it pays less than you are currently making.
Only focus on one area at a time to resolve an issue (e.g., relationships, finances, or health). Solving the problem will create a new level of confidence to address other issues (e.g., career, projects, or personal goals). Attempting to take on more than one at a time will inevitability cause burn-out and stress and hurt the progress you made (e.g., relationship with your boss – resolving an issue about handing in assignments late requires you to now hand in your assignments on time).
- Make the right decision for you. You can only make decisions with accurate information available right now, not what you wish you had or what someone else experienced. This is where flexibility is important.
- Make the best decision you can with what you currently know.
- Adjust as needed new information emerges. Having a coach or committed listener can keep you from jumping on information that may have no bearing on your goal or simply be fake.
- Don’t wait for perfect conditions; they don’t exist.
- Progress relies on beginning and stay focused, not continuing to think about it.
Remember, change is inevitable and stagnation is optional.
Effective legacy leaders keep moving and don’t wait for perfect clarity before taking the first action. They know that forward motion creates momentum and clarity.
Remember,
- You don’t need to figure it all out.
- You need to begin, adjust, and continue as you take the small steps required.
- Your confidence, competence, and ability will naturally strengthen as you move forward.
Consider hiring an executive coach to get you started and ensure you’re moving forward in a direction that supports your success.
©Jeannette Seibly 2026 All Rights Reserved
Jeannette Seibly is a legacy‑driven Talent Advisor, Leadership Results Coach, and Business Author. For over 33 years, she has empowered thousands of executives and business leaders to achieve sustainable success through strategic hiring, values‑based coaching, and intentional leadership development. Her work blends clarity, accountability, and soulful impact—activating performance and purpose at every level.