Occupational Adjustments: What I’ve Learned From Multiple Careers

7 min readJun 3, 2019
Image Pixabay.com/FotografieLink

In generations past, it was customary to go into a line of work and spend the majority of your life with that company, waiting for that day you can retire and enjoy life. Not anymore. Today, it is more common to change careers multiple times as we search for that job we both enjoy and can make a stable income from. Upward mobility is no longer about moving to a better position on the assembly line — now upward mobility can involve moving to new companies, new locations, and new opportunities.

Looking at my career, I have worked in a wide range of professions. I often say, “I am knowledgeable in everything while not being an expert in anything.” Perhaps not being an expert in any field is negative, but I view it as a positive. My first proper job started at fast-food restaurants, eventually leading to my adult life of working for large multinational tech companies. I have worked in roles as diverse as coffee shops and construction to engineering and project management. One thing I have learned over the years is that areas you think might not be related sometimes are, and things you learn in one field can make you better at another. Customer service skills obtained as a grocery store checker or barista come in handy when answering phones in a call center, just like the skills gained from theatrical performances come in handy when presenting to a room full of people at company meetings or conferences.

Relationships Can Last a Lifetime

Develop the soft skills needed to interact with people from all walks of life. When working for multinationals you will meet and work with people from all over the world. This is a fantastic way to expand your area of knowledge. Also, as you move around, those relationships might come in handy at a later date.

Depending on the field you are in, contracting is an excellent way to gain experience and cultivate a network of peers. As a business analyst and project manager, I was able to spend quite a few years finding contract work for different companies in similar areas. The nice thing about this is that often you have a set end of the contract date. This allows you to gain experience and relationships that will help you on the next assignment, and the contacts you make might benefit you later.

An excellent example of this is when I was hired full time at Microsoft. Prior to that, I had spent a few years doing a vendor assignment at the company where I met a few members of the team I would eventually apply to work on. During the interview process, it helped that many of the people interviewing me or who would work with me had already met me and could attest to the quality of work I had done on the vendor assignment. On paper, my CV wasn’t the perfect match for the role, but because of those relationships I had formed and the quality of work I had provided previously, they could recommend me for the position. That position turned out to be a great opportunity at a company I enjoyed for 5 years as a full-time employee. Many of the people I worked with there I still keep in contact with and consider friends.

Don’t Jump Around Too Much in Too Short of a Time

If an employer sees that someone moves from job to job in a short time, they might assume you won’t stay long enough for their investments to be worth the time. If you are looking to work for a company, plan to spend a couple of years there. Whenever I worked for a company, I would commit 100%, as if I were planning to spend the rest of my life working for that company. People see this level of commitment and extend an assignment, if on a contract. Or the company might offer other opportunities within the business when they see your commitment to the work.

However, be willing to change or leave if it is not working out. Sometimes we simply don’t fit within a certain environment. The flaw in staying there too long is that it will make you unhappy, the people you work with unhappy, and the quality of your work will decrease. If it isn’t the right fit, don’t force it, look for something that is a good fit. This is a mistake I made during my time at AT&T. After 7 years with the company, I moved to a team that did not mesh with my personality. This caused a lot of friction between myself and my immediate manager. If I had begun to look for another position at the time this became clear, I would have left on much better terms than waiting as long as I did, so that when I left I was as happy to be gone as she was happy to see me go.

Never Stop Learning

This is easy to say, and easy to believe we do. Do you read books; do you travel; do you watch documentaries? These are all forms of learning. But we can also take classes in areas that interest us, even if they don’t relate to our area of expertise. I’ve studied theatre, photography, and have certifications in Six Sigma (Project Management), video editing, and more. Each of these skills has come in handy in areas I could not have foreseen at the time I learned them.

Image © Alamy/Milo Denison

When I started taking photography classes, I was working as a customer service agent. Anyone who has ever answered calls from unhappy customers knows that it is not the most rewarding field to be in. To have a creative outlet, I took evening classes in photography, an area I always enjoyed as a hobby and wanted to learn more about. The advantage of the coursework was that it started with black and white film photography. I learned the basics of light and composure. I learned to use a light meter and the rewarding act of watching a picture work its way into life in the darkroom. This led to color photography, studio lighting, and more, which got me my first job as a photographer working for a company photographing graduations and another company as an assistant wedding photographer. All these I did while continuing my career in the corporate world. They were also skills I developed that came in handy 5 years ago when I left my nice well-paying job to buy a photography studio.

Taking a few classes in something I enjoyed led to owning my own business. And the years spent as a project manager helped with managing employees, workload, and the other day-to-day tasks associated with running a business.

Be Willing to Move

A nice thing about the world we live in is how mobile we can be within it. I had never been to Ireland in my life. But when I saw an opportunity within Microsoft to relocate, I jumped on it. The company moved

me to another country, doing the same work I was doing before. On the new team, I quickly moved to a senior role, they provided me an opportunity to manage others, and I became a primary source of knowledge among the team.

It can be scary to leave a nice comfortable job or home life. But don’t look at moving as a ‘what if it goes wrong’, look at it as a ‘what if it goes right?’ My sister had spent her entire life in Eastern Washington. She built a nice life there, had a lot of good friends, and it is where most of our family lives. She then received a job offer at a hospital in Montana. Not as huge of a move as one from Seattle to Dublin, but a big move nonetheless. When she spoke to me about it, my advice was this: what’s the worst that could happen? You could move, live there for a year and decide you don’t like it, then move back. Well, she moved, and she liked it. Now her Instagram is full of pictures showing the natural beauty in the state of Montana, her horse galloping around, and how much she is enjoying the great vast nature of the state. If you are worried about a move, just ask yourself, what’s the worst that could happen? You move, don’t like it, and move back. Better to have done it and know, instead of not, and always wonder “what if”.

It All Pays Off

As mentioned in a few of the examples above, my cross-business experiences have provided me with amazing opportunities I would not have had if it weren’t for the willingness to make changes and look for new experiences. I have lifelong friends from places I’ve worked for in the past, I’ve had the opportunity to move to other countries, and I can converse with people from all walks of life, but most importantly to me: one day when I am on my deathbed I won’t be thinking to myself, ‘what if.’ Be open to any opportunity that comes your way and don’t let fear prevent you from seeing where it might lead you, career-wise or personally.

Note: This article has been cross-published at milodenison.com




Milo Denison is a freelance project manager and content writer. His most recent book “How to Manage Your Manager” is out now www.milodenison.com/books