Can’t complain, still livin!

Lessons From 3 Bosses

We are all a product of our experiences. Places we've traveled, lessons we've learned and relationships we've built along the way. My career has been significantly shaped by 3 bosses. They entered my life at different stages and left an indelible mark on my approach to work and fulfillment. This week, I paused on my self-reflection and focused on the key managerial relationships that have, to date, shaped my professional journey.

Boss # 1

What was the gig? My first job out of college was an Analyst position in a small, M&A consulting firm.

My relationship with the boss. Initially, my perception of him was positive. He worked hard and cared deeply about his job. He worked long hours, even as he dealt with a recently diagnosed medical issue. Upon further review, however, his true identity was a passive aggressive, micro manager. He mistakenly thought he added value by changing my words on PowerPoint slides, which occurred on numerous occasions. His work days were long due to his inability to delegate tasks and trust his team. Thinking back, he treated his team the same way he was treated by the owner of the firm. It was clear the owner called all the shots; he checked in with him constantly. For a Vice President in the firm, he had little authority or influence.

What did they teach me?

  • Poor management rolls down hill
  • Micro management is not a management style
  • I do not flourish in controlling, passive aggressive environments
  • Long hours does not = value creation

Boss # 2

What was the gig? A contractor position at a mid-sized corporation. I came into the role with a few years of experience, but was still searching for direction.

My relationship with the boss. At first, I was intimidated by her. During the interview she appeared unimpressed by my qualifications. I remember she showed little emotion and was quite difficult to read. In fact, I clearly remember her blue eye color, because her eyes were constantly staring right through me. I thought I had bombed the interview and was taken aback when I received an offer.

This lady epitomized dedication and value. She had high expectations for herself, and her team. She was the type of boss that would step in the trenches with junior staff, if needed. Once, she asked my co-worker and I to come in over the weekend, to complete a project. Although I love my personal time, I did not hesitate when she asked. That's how much I wanted to impress her. I showed up in the morning and she was already there. She came in sans make-up and in jeans, ready to work along side me.

What did they teach me? This boss was my first coach and genuinely invested in my growth. She taught me the importance of finding my voice, which for a classic introvert, can be difficult. She would say, "Attending meetings and not articulating a point of view, shows little value."

Her advocacy increased my confidence in my abilities and planted the seed for continued growth. She encouraged me to travel, apply to graduate school and even buy a house. I'm proud to say that I've traveled to 3 continents, earned an MBA and felt the thrill of owning my first home. This boss also believed in paying it forward. Now that I'm a boss, I've emulated her approach to coaching and development, for my staff. It is a tribute to this boss and the impact she has had on my career.

Boss # 3

What was the gig? A mid-level digital strategy position at a mid sized corporation.

My relationship with the boss. My bond with this boss stems from the similar path we both find ourselves on. We are both creative people, that have reaped the benefits and accepted the costs of corporate gigs. We have both done well professionally, but are now facing a career crossroad. We also have a similar philosophy of work. We both believe work is a valuable component of life, but not the sole reason for existence. As a result, we've developed a relationship built on trust, respect and candid conversations. She is completely supportive of the journey I've taken to reignite passion in my work, and understands my current role is no longer a sustainable path.

What did they teach me?

  • The importance of honing a creative craft, outside of a corporate gig. Its easy to become consumed with the work that pays the bills. However, its imperative to summon up energy for your passions.
  • Taking the time to reflect on the life you want to have, should occur often. If not, the seeds of stagnation will grow.
  • Live the life you want to live, but understand that not everyone will agree with your decisions. That's ok.

I'm grateful to all three bosses for the lessons they have taught me. I'm quite fortunate that our lives intersected, exactly when I needed them to.

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