5 Important Questions to Ask Yourself before Making a Career Change

So, you’re thinking about changing careers. Whether your twenty-five or forty-five, it can be scary as hell when you’ve already invested so much in one pathway.

What if I can’t find a job in that new career? How can I live on an entry level wage again? What if my manager is half my age? Am I just wasting my expensive education?

Stressed guy in hoodie
Stressed guy in hoodie

I know how you feel. As someone who has changed careers ten times over a twenty-five-year span, I know a thing or two about how to do it and still progress into more senior roles.

My pathway?

· Casino marketing;
· Air Force contracting officer;
· Peace Corps volunteer (business and IT);
· NASA IT project manager;
· Digital marketing business owner;
· Procurement consultant that led to -
· IT Account Management in the same company and then another;
· Tea company owner;
· CEO of an animal welfare charity; and now
· Recycled plastic products business owner (current)

It’s been a crazy ride, but I admit that not all my career changes were that calculated. Some were driven by passion (that sounds amazing) and others on circumstance (i.e. the only job I could find when my family moved cities). Regardless, I have learned a lot about changing careers and how to continue to move to more senior roles while doing so.

So, if you’re thinking about a career change, consider the following:

1) What skills and knowledge do you have now that can transfer across careers and/or industries?

I started with a good foundation of transferable skills by getting two degrees in business, one where I majored in marketing. That marketing knowledge was useful in two junior roles and all my businesses. It eventually led to senior sales roles in IT companies and a CEO role (i.e. head fundraiser).

I also learned a lot about procurement when I was in the Air Force handling government contracts. That led to the procurement consultant role years later. Furthermore, I used this knowledge again just last month when I sent out Request for Quotes to manufacturers for my own business.

2) Are you willing to be the “dumbest” person in the room again?

Every time you change careers, there is a straight up learning curve. While you should have something to offer from previous experiences, a successful transition requires you to be hungry for knowledge like a child learning a new skill.

My consulting days were useful for learning how to learn quickly. Over an eighteen-month period, I provided advice to two government departments, a steel mill, a huge telephone services provider and a company that made chemicals for farmers.

There was no way that I could walk into these places as an industry expert. Instead, I was brought in because of my procurement knowledge. So, I often used this to my advantage to ask lots of dumb questions like, “I don’t know anything about steel making, can you please explain blah blah blah?”

To be the dumbest person in the room means that you can ditch your ego, but not your confidence to provide value. Asking interesting questions also makes the other person feel more comfortable as they realise that their knowledge is also considered valuable to you.

3) Can you try out the new career first?

Not all my career changes were as amazing as they might appear to be on paper. For instance, while being a Peace Corps volunteer was an amazing adventure, my day to day routine was incredibly boring and way too slow for my natural state. I simply didn’t have enough work to do even as I created new projects.

Later in life, I became more strategic in planning career changes. The best tool that I found for making such decisions was to write down the day in a life of (DILO) a potential new career. This meant mapping out the activities that would occupy the workday on a hour by hour basis.

Are you happy to be in meetings all day? Is dealing with customer service calls your thing? Can you handle the summer heat in that great gardening job?

If you’re not sure what a DILO looks like for a particular career, invite someone in that field to lunch and ask them. Or see if there might be an opportunity to volunteer to do something similar.

Of course, there are also plenty of articles and videos available online for most careers if you’re willing to spend time researching that way.

4) Have you done a personal budget?

Some of my pay checks dropped to almost nothing when I made a career change. How could I afford to do it?

For one, I knew exactly how much I needed to live on each month. When I was in the Peace Corps, I tracked each expense on paper and lived on a strict budget. While it required me to give up all “pleasure” food, I was able to afford one of the few internet connections in town even though it costed me about a third of my monthly wages.

Today, I still keep track of my expenses and live off a monthly budget. This has allowed me to save well when I worked in six-figure salary jobs so that I can afford to make these transitions to less paying jobs or even start a new business like I have done this time

5) Do you have the support of your family and friends to make this career change?

Career changes are hard enough. When you must consider other people in the decision, it can be the make or break factor of a successful transition. At some point, you’ll either 1) need the support of those closest to you to make this change; or 2) the new career must pull you so hard in that direction that you can intentionally ignore their opinions.

There really isn’t anything in between, especially when you go through the inevitable hard days.

Having shared my own career changes with you, it may sound way too difficult. In reality, I can’t imagine my life any other way. Rather than steadily climbing a career ladder in the wrong industry, I’m jumped across to others — usually with bigger and more exciting challenges. I wouldn’t be where I am today as a person or in my career had I not made those sacrifices or taken on those challenges.

While the scariest thing about change is the fear of the unknown, if you ask the five questions above first, you might find that the unknown really isn’t so scary.

Good luck with your next career move!

Purpose driven entrepreneur | Host of the Plastics Revolution podcast | Paddler of boats & boards | Check out my start-up journey at tvendange.com

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store