My Biggest Career Mistake: Sailing, Secretaries and Lime Green Pants

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I believe in the power of mistakes.

No one likes to make mistakes, of course. But that is where the learning happens. Bigger mistake, greater opportunity to learn.

What may have been my biggest career mistake happened very early on, while I was still finishing my undergraduate degree. I had my very first internship and was ready to conquer the world. Good so far. I also thought I knew exactly how to do it. Ha!

I was a lowly intern, feeling on top of the world that I had gotten “in” at a place that I very much wanted to work. The secretary in the department was very good to me, trying to help me out so I could make my way. But I didn’t take the cue.

Not only did I not yet understand that secretaries rule the roost (if not the world), but I did not appreciate that someone could make choices very different than mine and still have a lot to teach me.

Here’s the thing. This secretary (we’ll call her Nancy) wore lime green capri pants, corduroys and other outfits to work that in my naivety had judged as “not fit for the professional world”. I call myself naive not because I was wrong to recognize that Nancy would not move up the corporate ladder if she didn’t emulate the look of those at the top: dark-colored suits. She wouldn’t. Rather, I assumed that moving up within the organization was and should be Nancy and everyone else’s goal, without realizing that she had her own plan. One that was more carefully formulated than my 19-year-old point of view would allow.

Nancy wanted a place to work during the day (while she pursued her own interests on the side) that was forgiving enough so she could wear want she wanted and be whom she pleased. She was expected to conform to certain norms and left blissfully free to ignore other ones. She made calculated decisions to achieve the results she wanted. She knew exactly how to get where she wanted to go, but it wasn’t anywhere that I could have imagined.

So when Nancy pulled me aside one day to tell me that I should “follow the lead” of the head of the group (we’ll call him Troy), who wanted to talk about basketball and sailing a good part of the time, I ignored her advice. I wanted to ask Troy about things that interested me, and at the time these were not at the top of my list. While others joked and called him Captain Troy, I smiled through gritted teeth and pushed on for the certain set of experiences that I had expected out of the internship.

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After all, we were not on a yacht, we were in an office. I wanted to learn the ways of leadership and success, and they were not going to come from talking about sailing, I thought. At the time, I didn’t have a boat, or any family or friends with a boat. The one time I had taken an extended trip on a boat as a child, I had been seasick most of the week. I was bound to say something ill-informed, so better just to steer the conversation back to what was comfortable to me.

I couldn’t look bad if I just avoided topics that were out of my league, right Anyway, I reasoned, what did Nancy know, with her green pants and all? How could a chat about sailing be useful to me at all, other than to smile and humor my boss? Why would I encourage him to continue that conversation?

Turns out, Nancy knew a lot. In particular, she knew how to keep everyone happy while keeping herself happy. She kept these two goals in perfect balance, giving Troy and the group the support they needed while feeding her own needs. She intuitively understood that showing an interest in sailing was showing an interest in Troy. And that was the important part.

By contrast, I was being immature, overly serious and even selfish – holding on to the world as I knew it – by expecting to direct the line of conversation. And I was missing out on the chance to learn, bond, grow and have fun.

So, my biggest career mistake was actually a set of related mistakes:

Mistake #1: Discounting the message of an unexpected messenger.

Mistake #2: Closing myself off from new experiences.

Mistake #3: Making it all about me.

As I found out later, the green pants were a statement on Nancy’s part, a line in the sand that she was in a bridge job and had no pretense of “moving up” to a management position within that organization. She had her eyes on another prize – her own set of professional goals – but she also made sure to be so good at her job (orienting herself to the situation, as needed) that there was no way she would risk losing it over something as simple as wardrobe choices. In fact, as a highly creative person, she literally wore her authenticity on her sleeve. And she was respected for that by others in the group, including (in the months and years following my internship) by me.

I often think back to Nancy, the unexpected messenger, with whom I have lost touch in the over 20 years since I had that internship. I am indebted to her wisdom. I wonder if she has started her own company, maybe even a fashion line.

Nancy could have changed her style of dress any day. Changing my attitude took a lot longer.

From my biggest mistake, I learned my greatest lesson. It is not all about fitting in, it is also about being a fit.

Do You Need a Personal Board of Advisors?

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The board of directors of a company vidresses high-level business objectives, with voting authority and fiduciary obligations. A board of advisors is more informal, providing non-binding strategic advice that can benefit a start-up or smaller company by giving it third-party insights, encouragement, market knowledge, accountability, connections and other resources. Savvy individuals have come to realize that, especially in the new economy, we are each our own business to a greater or lesser degree, whether or not we officially operate as one. Does that mean we each need our own board of advisors?

Many successful professionals intuitively create a loose association of advisors without formalizing the relationships. They have mentors and occasional professional advisors that function in an ad hoc way to support short-term projects or “put out fires” in their business lives. This approach is a great first step, and formalizing this core group frames your trajectory in a foundational way and keeps you on the path to success.

Clearly, you do not need to hold meetings in a fancy boardroom with leather chairs or even get all of your advisors in a room together. While it may help focus the conversation, it can also prove a distraction if it is not a place or assembled group that feels comfortable enough to relax and creatively brainstorm and troubleshoot according to your needs. In fact, your respective advisors do not even need to know each other, since you are not a company for whom they are collectively setting policy but rather an individual seeking guidance, support, grounding and the oh-so-important reality checks. I do suggest, however, that you take more than an occasional, eccentric approach to incorporating one or more boards of advisors into your significant life and professional decisions. Have the infrastructure already in place for the moment of truth when you really, truly need it, so you can call on your advisors without triangulating their whereabouts or struggling to identify whom these angels should be.

I use the word “framing” above very deliberately. With my coaching clients, I often discuss reframing an experience to take ownership in a new way. For example, sales becomes less scary (and ceases to feel inauthentic) if you believe passionately in the service you are providing. A board of advisors becomes less of a foreign concept as an individual if you believe passionately in your own success and wish to give others the opportunity to share in that experience, with a willingness to offer your own help in advance or give back in return. Your passion fuels their willingness to be involved.

In my own life, I have found greater success in those periods that I had a “board”, whether it was a formal group of colleagues meeting on a regular basis or roster of individual mentors and professional advisors that I turned to regularly. Much earlier in my career, I was nervous or fearful that I was taking too much time from people who already had busy careers. At the same time, I failed to invest in myself, financially or otherwise, to get the professional insights that would have made a decisive impact on my advancement.

Why? I thought putting my head down and cranking out whatever was asked of me in the moment showed my “worth” more than cultivating relationships. My accomplishments would speak for themselves, I thought, not realizing the entire world that I was shutting out while I repeatedly closed my door to do some “real work”. I also failed to understand the value I would create by involving others in my experiences and sharing my insight for theirs in return. Value for all, not only for me.

Electing the right mix to your board of advisors and tapping into them is not  an exercise in taking – which is a dead end – but rather in creating value through meaningful personal interactions. In short, you are tapping into the electrifying power of collaboration in a formal way. By electing these mentors, colleagues and advisors to your “team”, you are fostering buy-in for your success. If you are respectful and show gratitude for their investment in your future, your newly-formed board can provide a critical backbone and sounding board to help you frame, keep sight of and reach your goals.

In a future post, I will discuss how you can assemble the right board for you.

Will You Bloom this Spring?

If you are located on the East Coast of the United States, as I am, you have been desperately waiting for spring to be more than a date on the calendar. Spring means warmer weather, pleasant outside gatherings and a fresh chance for a new beginning.

Yet unlike plants that have an internal guide on when to bloom, many of us have lost our intuition on the “where and when” of new growth. We carry the memories of too many prior Springs, where we have bloomed and then forgotten to water ourselves, or to get enough sun, only to end up foiling our own plan for new growth that Spring had so hopefully promised.

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What is the cure for the lost hope of a dozen of Springs past?

  • Trust yourself. Life is a process, not a study in perfection.
  • Keep yourself accountable for the changes you wish to see in your life. Find your own “Board of Advisers” – just like the Board of any company, find the Board of You.
  • Set your goals and prioritize your time to reach them. May you look back to today, this Spring and this year, and feel that you used your time to set your own path (years, weeks, days, hours, minutes and seconds – they are yours).
  • Surpass obstacles, like the plant that blooms around the rock.
  • Approach life with an open hand, ready to receive what you seek. The closed hand receives nothing. In the same way, if you grasp at every opportunity, you will lose your focus when the right one is presented.

Will you bloom this Spring?

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Game-Changing Decision – I’m Launching a Business & Executive Coaching Practice

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Friends and colleagues, I have made a game-changing decision. Some of you have already heard, as emails and successive social media posts create a series of “mini-launches” rather than one definitive LAUNCH.

I am hanging up my shingle, stepping aside from the practice of law, and launching a business and executive coaching practice geared toward attorneys, executives and entrepreneurs. More details to come soon, as I work on reconstructing the SEGAL LAW BLOG into my new coaching blog.

In the meantime, here’s my new website: www.segalcoaching.com.

Thanks again for all of your support!

The best is yet to come.

-Anne Marie