Even Successful Leaders Fall into a Hole Now and Then
Posted February 22, 2019

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Climbing Out of a HoleKristen started, grew, and sold a company. The liquidity event was very, very beneficial for her. She had since moved to a new role in another company. She wasn’t the CEO this time, and was brought in by a friend to serve as a transformational leader in this new organization. Things weren’t going as planned. She was not fully engaged, and wasn’t delivering the value she knew she could offer. She wasn’t exactly mailing it in, but she wasn’t playing at the top of her game either.

Kristen wanted something different but she didn’t know how to get started. She needed a push to start climbing out of her hole.

At the Bottom of the Hole

Even successful leaders have trouble breaking out of the funk that happens more often than you might think. Because Kristen had made a lot of money in the sale of her other company the expectation is she would be able to be successful and fulfilled wherever she went. It doesn’t necessarily happen that way. Sometimes there is clear evidence of being stuck, other times it is more subtle.

Think of being at the bottom of a very deep hole. It’s so deep and dark you can’t see a thing. You know where up is, but it seems too daunting to even start the ascent. You don’t know where the nearest foothold is to get started, and it’s unclear how much effort it will take to get to the top. Because of this dark and seemingly desperate situation, an unwillingness to take any action takes over. It’s scary, and even though it’s crummy, it’s what you know.

In Kristen’s situation, she was in that dark place.

Before you get out of the hole, let’s get an idea of what got you there in the first place.

3 Things That Put Us In The Hole

  1. Expecting the tide will always carry us.

People who have had success often feel there will always be that tide to carry them onward and to other great things. Personal or professional accolades and rewards are a drug that can motivate us to head to other great things, and also serve as a looming threat in case things don’t work out.

In Kristen’s case she was sought after to step into this role. She thought that what got her to this point will continue to propel her forward. As soon as there were some hiccups (financial and personnel) she became disenchanted. It wasn’t such a smooth ride. Rather than looking for ways to understand and/or address the situation, she began to slip into the hole.

New business owners experience this all the time. The excitement of launching the company and closing the first few deals leads to the expectation of a nice, linear trajectory of growth. When this doesn’t happen, the leader can slip into a place of self-doubt and has trouble being hopeful. You become more fearful and negative, your executive brain function starts to lose its impact, and you are unable to solve problems and look for creative solutions.

  1. Blaming others.

When you are scared, frustrated, or angry, it’s easy to place the blame on others. Kristen readily blamed the management of her new company for not being fully clear on the financial situation of the company. Outright she said, “I wouldn’t have come here if I knew this was the case.” She also felt the talent she had to work with wasn’t up to her standards. Kevin, the guy she thought was going to be her “go to” guy was way less experienced and less competent than she was expecting.

Of course there are external factors that cause obstacles for us to move forward. We have a choice of how we show up in those cases. When in the bottom of the hole it’s easy to blame everyone else for landing you in that place. With righteous indignation, a feeling of entitlement, or just an unwillingness to look at our decisions, we can blame others for the way we are feeling.

Unfortunately blame is not a pathway out.

  1. Losing touch with our values.

As we start slipping into that hole we can lose our north star; the reason we do what we do.

Metaphorically, we can’t even see the stars at the top of the hole and we don’t know what to do.

Kristen had lost her focus personally and professionally. At home she wasn’t being the mom and wife she wanted to be. She was admittedly cranky and no fun to be around. The impact on the home life was significant. She had worked hard in the past to successfully create a stable foundation for her family. She used the skills and experience she had to achieve the goal of creating and leading that first company. She valued family, hard work, achievement, excellence, and continuous innovation to motivate her during those demanding years.

She had lost touch with those values and the impact was being felt at home and at work.

Climbing out of the hole is tough, but it can be done. Acknowledging this is not where I want to be and I want to do something about it is the necessary first step. Moving up and out of the hole is hard to do on your own, and that’s where seeking help comes in. Finding those trusted resources – personal and professional – will start pointing you upwards. Depending on the circumstances, coaches, consultants, therapists, mentors, family members, friends, and colleagues can all be valuable sources of support.

Working with such resources, there are three steps you can take to start the climb out and back to being who you want to be and be doing what you’re meant to do.

3 Tactics to Climb Out of the Hole

  1. Reconnect with what worked in the past.

You are not the ineffective loser you feel like you are when in the bottom of the hole. You are probably having trouble making decisions, and second guessing the decisions you do make. It wasn’t always the case. Force yourself to remember (make a list) things you did that worked in the past and stop your inner critic from saying it wasn’t a big deal.

Make a list of your strengths and dig into what the value of those strengths were. Know you can do things that others cannot and as a result amazing things happened. Ask others to identify the value you deliver and how they see you being able to have an impact. The things that come most easily to us (our strengths) are often the things we take for granted.

In her previous roles and in creating and selling her company, Kristen had exhibited skills of creativity, conflict resolution, discipline, learning, team building, and problem solving in addition to technical skills. These had not gone away! As she started to think about those skills she began to start to see a way out of the hole. She could help the new company look at their current situation differently (creativity). She could work with her colleague Kevin to help him grow in his role and learn the things that would help her, him, and the organization (team building).

As soon as she started reconnecting with her strengths, she could see how to apply them to drive change and to feel like she was contributing again.

You have a unique set of gifts and skills that are meant to be used at this point in time. You’ve done it before and there’s no reason you can’t do it again.

  1. Rediscover your passion.

When you are unable to feel good about where you are or what you are doing, it’s very difficult to create a vision for a path out. Our primitive brain has us in that place of fight or flight, and we are unable to create or inspire others let alone ourselves. One way out is to start to rediscover your passion.

Passion = What you are good at (strengths) + What you like to do

If you actively sought out your strengths in step 1 above, you are halfway there to uncovering your passion. Now what do you like to do? Really like to do? Try asking yourself the question, “I know I can do it, but do I want to do it?” This frees you up to start really defining what you like to and stimulates that desire to start the climb out of the hole.

Kristen began to realize she was really good at creating and innovating new ideas. She was also great at building teams. From her past experience, she also realized she liked and had the courage to build things from scratch. She wasn’t afraid to step into the unknown, because she had the proof points of success. In fact, she was passionate about creating and making things happen.

  1. Take baby steps.

In the bottom of the hole you can’t see where you can start the climb up. You don’t even see the light at the top of the hole. You know there’s a way out and you have to believe that if you start taking any step at all it will get you away from the place you are that doesn’t serve you. It’s scary, but you know there has to be something better.

Small steps get you started. Kristen started by sharing with a friend how frustrated and stuck she was feeling. This friend made the referral to a coach and she started a coaching engagement. She sat down with Kevin, the co-worker she didn’t feel was competent, and started working with him. Rather than blaming him, she used her skills to help him grow and have greater impact. That felt good. She started to reconnect with others who had helped her start her previous company. Was there the opportunity to “get the band back together” and create something new? She made the effort of not bringing here woes home each day and dumping them on the family. They were able to be more supportive of her and the general mood of the household shifted. This led to her being better able to see something different in her future.

These baby steps don’t propel you out of the hole immediately. Rather they help you start the climb. You feel a place to put your foot and take a step up. This leads to another step. You feel a ledge with your hands and you pull yourself up even further. There is a dim glow of light at the top of the hole so you know you’re going in the right direction. That light gets brighter and more distinct with each step. Suddenly you can feel a breeze and smell fresh air. It’s been awhile since that was the case. All of this reinforces you desire to keep pushing forward. You’re using your strengths, aligning with your values, and your energy is shifting as it becomes more and more clear what your next move will be.

You’re out of the hole, back on solid footing, and the opportunities for what’s next are laid out in front of you.

The down times are inevitable. They don’t have to keep you down for as long as you think.

Tim Ressmeyer is a professional leadership and life coach. He is also the author of The Impact of Confidence: 7 Secrets of Success for the Human Side of Leadership (2018). Available on Amazon.

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