Leadership at 2 am

On LeadershipChat this week, we’re discussing the things that keep a leader up at night.

My lovely co-host, Lisa Petrilli, has written an excellent post that gives the corporate/executive angle: Four Priorities Keeping CEOs Up At Night. I urge you to read her thoughts as we prepare for the Tuesday night on-line discussion.

I’m a solopreneur, and generally sleep pretty well through the night (now that our kids are older!), but as someone who is seeking to lead in a different sphere than a corporate hierarchy, there are definitely things that can cause tossing and turning. Perhaps you can relate.

1. Focus – A person working on their own, or in a small business, seeking to lead him/herself, clients, and partners, must first and foremost learn how to keep their eyes on the ball. The great trap of those in a more entrepreneurial environment is often distraction rather than disruption. Interrupted sleep regularly involves trying to decide between three divergent paths, each seemingly legitimate – and without a very sharp and clear focus, the leader can ping-pong back and forth between options, unable to set a firm direction (shameless plug for one my services: that is why a Brand Therapy session, where you identify your professional DNA and direction, can be so critical).

2. Isolation – This is a major problem for leaders at every level. Without a supportive and wise group of peers and/or colleagues, leaders can lose plenty of shuteye carrying the weight of the world on their shoulders, with no mechanism for gaining perspective. Fortunately, social networking allows people to find like-minded leaders and to create a web of support and wisdom that can prevent the turmoil of isolated leadership. A few choice words from a different angle can sometimes resolve a conundrum that has interrupted a week’s worth of sleep.

3. Weariness – Those leading new or small endeavors are constantly creating, constantly pushing forward, leading every moment – and this can wear down our resiliency and lead to to very restless nights. Sometimes, the relative structure of a corporate environment, where you’re pulling only some of the weight in a more defined area of responsibility, sounds quite appealing – and, indeed, for some, it may be the right option. But for those looking to break new ground, the unrelenting nature of the  yoke we have chosen to shoulder can wear us down. When everything seems to depend on you – that’s a lot of pressure! And I don’t have a good answer for this one. Still trying to find equilibrium here…(suggestions??)

So, what keeps you up at night? Tonight at 8 pm ET, let’s discuss! You’ll find the LeadershipChat community to be very warm and supportive, people who are wrestling through the same things you are, and coming together to support one another (see point 2 above).

And, to make your chat experience even more enjoyable, try out ChatTagged, a custom-made Twitter client for helping manage your on-line chat interactions!

(Image credit)


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About Steve Woodruff
Steve Woodruff is a blogger, a Connection Agent, and a consultant in the pharma/healthcare industry. He specializes in helping people and companies make mutually beneficial connections.

3 Responses to Leadership at 2 am

  1. Pingback: May Topics « Leadership Chat

  2. Kenny Rose says:


    I would add unfilled potential a desire to deliver impact beyond ego. A selfless desire to contribute and to remove some of the economic and social inequality that tarnish our world.

    Solopreneurs have to be driven. We do not have the comfort of not acting or adhering to corporate policies for the sake of it because we still get paid. We don’t have a comfort zone.

    We are self directed. Seek self actualization and impact.

    They are my driving forces limited by an awareness impact has to go beyond ego.

    Interesting post Steve.

    Looking forward to leadership chat. As ever.

    Hat tip to you Sir.

  3. I wish I had been able to participate more this evening, but work took precedence. For myself, what keeps me up at night are (in no particular order):
    1. Frustration with projects: Either they are not going the way they want, or there are enough of them, or I want to do something and I am being held back by red tape…there are a variety of “project” based items that keep me awake.
    2. Wondering about the future. As confident as I am in myself and my business, it is definitely scary to think about where things are headed. The concept of not having business tomorrow is terrifying, but so is the idea of too much business to handle that I don’t do a good job. I just wish I could know what lay ahead for me…
    3. Personal time: I often feel like at the end of the day, I am missing out on being a wife, a dog owner, a normal person…and that is a tough thing to handle. But, I do realize that at some point I will really be able to enjoy that time…and that is what I look forward to!

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