Money & Career

How to get your dream job

It's never too late to make a change. Get inspired by these people who took the leap to transform their professional lives for the better.


Photo, Roberto Caruso and Sian Richards.

It’s a hot, muggy evening in downtown Toronto in 2009 and Gordon Dennis is doing his usual Monday-night thing: hanging out at Second City comedy club, indulging his passion for making people laugh. It’s drop-in improv night and his turn to be on stage. Dennis’s challenge is to make his audience laugh and he’s a master at it.

The audience’s roars that night gives Dennis, who has spent 25 years in the financial services industry, a huge rush. That’s important because for the last few years, Dennis’s life had been stuck in a rut. But while on stage, he has a revelation that sets his life on a different path. “I realized how much I loved being on stage and making people laugh,” says Dennis, 56. “That’s the moment I decided this is what I want to do full time. It’s more than a hobby for me. I needed to figure out how to make it happen.”

Most of us can identify with Dennis. (We’ve changed his name to protect privacy.) Who amongst us hasn’t felt the desire to make a career change sometime in our life? It’s something that impacts the 45-year-old stay-at-home mom who wants to get back into the workforce, the highly paid football player who gets injured early in his career, and the young MBA student who has lofty academic credentials but no clear idea what to do with her life. All of them want to make a change and need to invest some time and money in themselves to find a path that will make their lives better.

That can be tricky, mainly because our passions often clash with our practical responsibilities. Achieving our dreams while paying the bills can seem completely incompatible. But the truth is countless people have built careers for themselves that sustain them both financially and emotionally.

Gordon Dennis, for one, is well on his way to transforming his interest in comedy and acting into a new career. As an investment adviser earning $85,000 annually, he had to make some choices. Knowing he didn’t want to quit his day job without understanding fully how a career change would impact him, he started with small steps. His wife, now semi-retired, encouraged him to pursue his passion. “She said that every time I came home from my comedy classes I was so fun to be around that she wouldn’t hear of me stopping,” says Dennis. “That support was really good for me.”

Early on, Dennis started preparing financially for the change. He began contributing more to his retirement savings and delayed expensive travel plans to get ready for the day he would work full time in acting — a career he knows will probably pay less than his present job. To get ready, he spent two years taking comedy and acting courses. “My first goal was to train. My second was to do enough paid acting annually to cover the cost of my classes,” Dennis says, “I achieved those goals the first year and surprised even myself.”

As Dennis has learned, the key to success is in harmonizing your life and financial goals. “People compartmentalize money and life goals,” says Jerry Gale, director of the family therapy doctoral program at the University of Georgia. “It’s only when they start talking about what they love in life that they see the two are connected.”

Identify your passion

The world is full of naysayers. Many can be found very close to home. When you’re exploring your passions, it’s important to surround yourself with people who will champion you and your goals — good friends, colleagues, and life and career coaches who can help you along the way. “If you’re married or in a committed relationship, your spouse needs to be on side,” says Caird Urquhart, life coach and founder of Newroad Coaching in Toronto. “Or in my experience, either the new career or the marriage will fail.”

To make sure you’re on the same page, have an honest talk about what you’re hoping to accomplish, how much time it will take and how the small sacrifices the two of you make now will help tremendously in enriching both your lives.

That’s what Martha Reeve, a Toronto-based stay-at-home mom with three young kids, did in 2011 when she decided to get back into the workforce. “I knew there was something more I could be doing — giving back,” says Reeve. “I really missed being engaged with people in a professional way.” With a Master’s in Architecture, Reeve’s husband encouraged her to find a third party — a life coach — who could help put her on the right track. “My life coach was an important part of the process,” says Reeve of Urquhart. “She helped me identify my passions as well as a future career path.”

Of key importance, Urquhart had Reeve pinpoint the time in her life when she was the most fulfilled in the workplace. Doing this allowed her to hone in on a time in her 20s when she worked for an architecture firm in London in interior design. At that time, she had engaged in art selection for buildings and corporate headquarters. “The most creative time in my life was working on that team,” Reeve recalls. “That’s when I realized I could get back into art. I wanted to combine art with helping people. Just realizing that was key to taking the right path for me.” Today, Reeve runs her own art consulting business from her home office, advising personal and corporate clients on purchases. She couldn’t be happier.

She started off by contacting art consultants already in the field. “I just called them up and had informational chats with them,” says Reeve. “How did they run the day-to-day business? What was their fee structure? It was great nuts-and-bolts information that I really needed to get the business started.”

Then she drew up a letter describing her new business and emailed it to friends, family and anyone else she could think of. “I got great feedback,” says Reeve. “People said they didn’t know I was doing this and I started getting some business right away. I started frequenting galleries and schmoozing with people there, as well as volunteering my services at silent auctions, where I was able to offer art consultation sessions to paying customers.” Today, Reeve’s business has 25 clients and revenues have grown steadily every year.

John Hierlihy, a partner at career management and executive search firm 21st Avenue Partners, says Reeve did a couple of key things right. “First, she looked back at an earlier stage of her life to see what activities and career situations gave her the most happiness and satisfaction,” Hierlihy says. “Then, she set out to include those passions in a future career.”

That’s what former CFL football player Rob Kochel did several decades ago, when at age 25, he crashed his motorcycle, breaking his shoulder. Kochel, who today is vice president of national accounts at Invesco Trimark in Toronto, never played football again. But after some self-evaluation he realized he already had a lot of skills that would be easily transferable to other careers. For instance, Kochel had worked part-time as a commercial realtor while in the CFL and had experience that would be useful in any sales or marketing job. “I also did a diagnostic questionnaire and that was helpful,” says Kochel, who landed his ideal sales job with Labatt Brewery in 1980 and later at Clearnet Communications (now Telus) in the 1990s. “All my sales and research skills were transferable and that’s empowering. Sometimes you have to jump to another ladder — get into a new industry. Even if you have to take a pay cut, that’s usually short term and can be a very good strategy to eventually get ahead.”

Hierlihy agrees, adding, “Just look closely at the common links — personal traits, contacts, friends — that can be transferred to this new world. That’s crucial to success.”

Examine your finances

Before you contemplate a major career shift, get your finances in order, advises Trevor Van Nest, a money coach in Newmarket, Ont. “Life is all about transitions. You don’t know when they’ll come but you have to be prepared for them.” Start by writing up a budget. Making a career change may require cuts to spending, especially discretionary items (like travel, furniture and entertainment) until you have established your new career. “Keep the budget simple,” says Al Feth, a fee-for-service planner in Kitchener, Ont. “Protect your home and ensure you can pay the family’s heating, hydro and food bills. Everything else can wait.”

Next, examine your savings. “Everyone should have six months of cash in an emergency savings account,” says Feth. “It could be in money market funds or a high-interest Tax-Free Savings Account.” That money may come in handy to help you transition into a new career. You may need money for courses or simply to balance the household budget until you get a full-time job you love. “The key is to prioritize your expenses and remember this austerity plan is just temporary,” says Sheila Walkington, co-founder of Money Coaches Canada in Vancouver.

As well, consider tapping RRSPs. If you return to school full time, you can make tax-free RRSP withdrawals through the Canada Revenue Agency’s Lifelong Learning Program (LLP) that must be paid back to your RRSP within 10 years. It may also make sense to withdraw small sums from an RRSP to cover living expenses if you’ll be in a low tax bracket. But check with your tax accountant first and also bear in mind that, unlike the LLP, you’ll never be able to regain that RRSP contribution room back.

If you don’t have enough savings to launch a new career, consider sticking it out at your current job until you’re ready. That’s the route Joel Samuelson chose. From 1999 to 2005, Samuelson, now 38, worked as an auto parts assembler in Alliston, Ont. (We’ve changed his name to protect his privacy.) In 2006, he decided to make a dramatic career change with the goal of working one day in the civil service in Ottawa. Samuelson, who was making $15 an hour at the plant, wanted something better. “It was stable work but the future was limited,” he says. “I knew people who whined about their jobs at the plant but never did anything about it. I didn’t want that to be me, so I made a plan to change careers completely.” He had a journalism degree but decided he wanted to take a year off to get his MBA. For two years, he worked at the plant and saved money. When he had enough for tuition and room-and-board — about $30,000 — he asked his employer for a one-year leave of absence. “I didn’t want to go into debt, so I saved like crazy before I took the leap,” says Samuelson.

He got a part-time security guard job on campus, working the evening shift three nights a week to earn extra money for incidentals. When he graduated in 2007, he moved to Ottawa. After a short-term contract as an administrative assistant, he landed a full-time job in the department of immigration. “It’s a stepping stone,” says Samuelson. “I’d eventually like to work for the diplomatic corps. That’s my next career goal.”

Create a plan

The key to effective action is to have a clear idea of where you want to go. “We sail, and if we don’t know our destination, we may end up where we don’t want to be,” says Rusty Rueff, a director at Glassdoor, a career website based in Sausilito, Calif. His advice to people thinking of making a career change is simple. “Always be running to something; don’t run from something,” Rueff says, “And it should always be to more than just one thing—never just about money. The key is to be able to do what you want to do, where you want to do it, and with the people you want to do it with. That’s the endgame.”

Sometimes all that’s needed is to take some very small steps. “You could decide to make the time at your job more vibrant,” says Ruth Hayden, an author and financial educator in St. Paul, Minn. “Bring donuts one morning a week for your colleagues, do a yoga class if it’s offered, or join your company’s volunteer committee — or do all three.” Alternatively, you may chose to stay at your job but build an active and vibrant life after work. “Even though you may decide your job is where you have to stay, you have to decide it for yourself. That’s key.”

Rueff agrees, adding that people have to be responsible for the risk they take if they have children. For instance, you may want to be a comedian, but what else do you want to be? A good dad? A little league coach? “Those things are important too, and belong in your plan,” says Rueff. “You may not be able to make a huge career change at this stage of your life but making sure your family’s bills are paid and that you’re active in your children’s life are admirable goals. Your dream may need to wait five years before you initiate a change but that’s okay. The people who make this conscious choice themselves are more self-actualized than anyone else.”

Of course, if you decide you need to change careers —now or in the future—research everything you can about the job you’d like and the place you’d like to eventually work. “Arm yourself with information,” says Rueff. “Become familiar with the company and everything it does.” Enroll in a course, find a mentor, volunteer in your field of choice, shadow someone that you admire for a day, or read up on a field that interests you. “These are baby steps, so there’s no need to quit your job or overhaul your entire life,” he says. “Starting small also gives you the opportunity to dip your toe in without taking the full risk that may come later.”

Life coach Urquhart asks her clients to write down their criteria for the perfect job. “That allows the mind to open up and spill out all the possibilities open to you,” she says, “Once they have the perfect job nailed down, they can start looking for something that has most, if not all, of the desired qualities on your list.” Hayden adds that it’s also helpful to keep a notebook and log all the small steps you take each week to move towards your goals. “It feels more real,” Hayden says. “Writing these small accomplishments down on paper shows progress and progress is inspiring. Patience is key.”

In fact, aspiring actor Gordon Dennis says he wrote up his transition plan and broke it down into one-, three- and five-year goals. He also made sure he did one thing every day that would get him closer to his dream career. “Right now I’m trying to lose about 20 lbs because I think it will allow me to get more acting work,” says Dennis. “So every morning, after 30 minutes of exercise on my stationary bike, I check off in my notebook that I’ve done it that day. It’s very motivating.”

Put your plan into action

In 2009, Matthew Zageris was unemployed and frustrated. The Montrealer had been laid off from his accounting job and longed to find a path to a marketing position. “It felt terrible that I had spent three years learning about marketing in college, only to take on accounting roles I did not enjoy,” says Zageris, 28. “But after I graduated I had student loans and needed a job—quickly. That was the financial reality.”

Deciding his dream job lay somewhere in the marketing department of a high-tech company, Zageris became strategic in his job search. He focused on getting any entry-level job at a tech company in Montreal. He got one in a small tech company’s accounting department. After a couple of months on the job, he asked his boss if he could work one day a week in the company’s marketing department. This gave him some marketing experience that he put to good use after he got laid off again in 2012. This time, with marketing skills on his résumé, he was able to land a marketing coordinator job. Then, at his job review last fall, Zageris asked for a title change to “online marketing specialist.” “I didn’t get a pay increase but that’s fine,” says Zageris. “I’m now in a job for which I have a passion.”

Ultimately, shaking hands and building relationships is key to expanding your options. “Don’t hide behind a résumé,” says Feth. “Get the Rolodex out and dust off past contacts. Someone you’re already connected to could be key to getting you to a new stage in your life.”

Take ownership of your career path and keep moving forward. “Initiative is important,” says Urquhart. “If you don’t have it, it’s difficult to learn unless someone shows you the way and holds you accountable.”

But for those who take the initiative, the results can be exhilarating. Dennis is now coming up to the end of the fourth year of his five-year plan. He has an agent and has landed several small parts in TV dramas. “I have a very busy little sideline, and I love it,” says Dennis, who continues with his day job to pay the bills. But not for long. “My goal next year is to get 100 days of acting work and earn about $40,000,” Dennis says. “I really think it will happen and when it does, I’ll quit my job and pursue an acting career full time. With a little financial planning, my wife and I can live on those lower earnings and I can do what I really love full time. Life doesn’t get much better than that.”

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