Career Advice 101 – Observations looking back over many years

When I was in my twenties and thirties, I didn’t have a career plan. Even though IBM invested heavily in employee development, I never took career planning seriously and unlike many of my peers, I never aspired to become a CEO or senior executive. I didn’t know what I wanted to do and worse, I stubbornly didn’t believe anyone could predict their future so why spend energy trying to plan it. As a result, my career journey can best be described as serendipitous versus strategic.

Over the past 38 years, I have ascended to senior positions and achieved financial success and career accomplishments that I never dreamed of. Nevertheless, the path I followed was unplanned and relied on good luck, fortunate timing and mentors and managers who saw something in me that I did not see in myself.

My career also could have been self-destructive.  Looking back, I can clearly see many forks in the road where, if I had chosen to take the other path, the outcome would likely have been disastrous.  For example, in the early 1990s when many of my peers were voluntarily or involuntarily leaving IBM, I almost accepted a job with a company that ended up bankrupt three years later. Had I taken this job, I would have never worked for the greatest career mentor that I had in my life.

With the work that I do today and because of my large network, I am often asked to provide career guidance to people who are early in their careers. Like I was, they are struggling with defining their career objectives and a path to get there. Unlike me, they understand the importance of devoted energy to this task.

Even though I was unable to plan my own career, with the benefit of almost 40 years at IBM, PeopleSoft and leading my own company, hindsight has helped me give advice that I never had for myself.

My first epiphany was that your resume is like a product; a collection of skills, experiences and attributes that define who you are and what future jobs you could do.  This is not dissimilar to the features and functions you would find on a product specification sheet. If five years from now, I want to be a Vice President of Sales for a software company that sells marketing solutions to large banks and insurance companies, then it would make sense that my ability to get hired for the role will be aided if I havea  skills, experience and attributes such as:


My second epiphany was that you cannot change everything about yourself overnight. Do you remember experiments in your high school science lab? When done correctly, you only changed one variable at a time. Similarly, this rule applies metaphorically to career planning. If I am currently employed as a software developer working for a company that develops applications for the consumer market in the telecom industry, it is unlikely that I know much about selling marketing solutions to large enterprises and certainly do not have the track record of success.  In the multi-dimensional model of career planning, consider the number of vectors (variables) in play in the transition between these two roles:

To arrive at my career planning epiphany, I combined epiphanies 1 & 2. By assessing a person’s resume and deconstructing it into a list of current competencies, a portrait of a person’s as-is” model appears. By picking a point in the distance (5 years, 10 years, 20 years or more) and describing the desired role, that role can then be deconstructed into a list of competencies required to be considered for the position. Matching the “to-be” against the “as-is” creates a gap analysis, which will direct a person to the interim roles they need to develop on their way to the future desired role.

This is where patience comes into play.

In a recent Globe and Mail, I read an article: Laura Dawson: ‘My career path is unorthodox; I stumbled from one thing to the next’. In it she is quoted as saying: “When I was a professor, students used to be in states of angst, stressed they weren’t on the path they thought. You can do a lot in your 40s and 50s, important and worthwhile things.” “Give yourself a break if you’re 25 and stressed.”

This quote resonated. Many people I talk to are trying to run their career as a sprint, when reality, it is a 30 to 40-year marathon. When I was 30, I could never imagine myself as 62 years old. Today, I work because I want to and love it, not because I must. You may end up the same. Don’t feel you must cram that desired role you want into the next 5-year plan. Play the long game.

By serendipity, not design, I played the long game. My industry sector skills are incredibly broad and reasonably deep from working with clients in almost every sector. My experience and domain skills in technology and software cover everything from sales and marketing to professional services, HR, finance, product management and development. My customer focus is Business to Business (B2B), not Business to Consumers (B2C) but ranges from small business to large, global enterprises. I have held roles from being an individual contributor and subject matter expert to being a senior executive in strategic roles. I have managed teams ranging from a handful of people to a division with over a thousand employees. This isn’t bragging, but it does allow me the flexibility and options to do almost anything at this stage of my career.

Another great article that resonated with me was Daniel Debow’s recent post Forget about your “career path”. Embrace a career stumble

After almost 40 years of stumbling along a career path, here is my simple advice that I now share with everyone who asks.

  1. Start with an honest and realistic assessment of who you are and what is your current inventory of skills, experiences and attributes. Ask yourself what this qualifies you to do (What possible jobs or roles)?
  2. Pick a point sometime in the future. Start with picking what job you would like to have three jobs from now. Given that most people will need to spend between two and four years per role to gain the skills and experience the job offers and prove a track record of success, this amounts to roughly ten years of your career. Next, define the skills, experience and attributes you will need to have in your inventory to get that role you aspire for. This is your gap analysis.
  3. In each of the three jobs between now and your aspirational job, you can likely only change one or two of the vectors or variables discussed above. For example, if you try to jump from a software developer to a sales role, while changing from a B2C to a B2B marketplace, and switch companies, and learn a new customer industry all simultaneously, the odds of being successful are stacked against you. Therefore, plan your next three jobs to each fill in only one or two major competencies identified in your gap analysis.
  4. Execute your plan. With each new role you take, advance your timetable to add a new aspiration role three jobs from now. Rinse and repeat the process above. As you mature in your career and life, your aspirations will also change and can be factored into your plan.

I hope this process gives you a method to approach career planning and wrap your arms around a complex task. Predicting the future is never easy.

© 2017 Meaford Group

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