11/04/2011 04:29 EDT | Updated 01/04/2012 05:12 EST

Second Careers: How to Make Yours a Success Canada's Guide to retirement living

The financial outlook for many cash-strapped boomers' retirement years is murky at best with the worry of making money last over longer life spans, higher medical costs as time goes on, fewer company pensions and the challenge of finding new work after retiring or being laid off.

But if you're a practical optimist, the financial prospects for your retirement years have promise -- as long as you have a plan and think things through.

As with any major life decision, you need to do your research and then develop a strategy; one that is flexible enough to change if necessary.

Crunch the numbers

Visit your accountant and financial planner to discover:

  • Whether you have enough money saved to survive for a year or so of unemployment while your new job or business venture takes off
  • How much money you'll need to earn to maintain a decent standard of living over the next 20 years
  • Creative ways to trim your current budget
  • How to maximize your assets so they'll last longer
  • Whether you should re-mortgage your home or take out a line of credit

Critically assess what you have to offer in your next career:

  • What are you passionate about? Always aim to do what you love.
  • What experience and knowledge do you have that makes you unique?
  • What do you have to offer that people would pay hard earned cash for? And who are those people? Drill down to figure out the exact demographic your new venture will be targeting. What do they need and want and how can you give it to them?

Some of the most popular encore career fields are:

Health care





Get web-savvy:

  • Build a compelling and professional presence on LinkedIn. It's really the 'six degrees of separation' of the work world and you need to be there -- no matter what industry you're in.
  • Become part of the community on Facebook and start a Facebook page for your business once it's up and running.
  • Join Twitter and follow companies and people whose products, ideas or interests complement yours. When you find relevant articles or sites, tweet about them and become part of the conversation.
  • Use Google and other online tools to stay abreast of the latest news on your industry

Newbie 55

Many people make the mistake of starting a new career from scratch right after they retire. Being a newbie at 50 or 55 is a dangerous thing; you've got very little experience, some grey hair -- or not too much of any colour -- and you may be a little slower out of the gate than your 27-year-old competitors.  Don't set yourself up for frustration or failure.  This is an odds game so do everything you can to set them up in your favour.

Get connected

A better idea is to test out your next career by working at it on the side while you are still employed.  Retrain, volunteer, or work as an unpaid intern and get to know the job, the people and the culture before making the leap.

If you really want to start a new business, do your research while you're still working, build a network of contacts by volunteering, working as an intern and joining relevant professional organizations.

Take your time

Take all the time you need to make yourself as competitive and well-connected as possible before looking for work or launching your business. If you've done your financial homework beforehand, you'll know how long your money will last before you make your move.

If you are a younger boomer and you can wait a bit before you start, do so. After the older boomers ahead of you retire there may be more jobs available and companies may be hiring because there will be a smaller workforce and fewer skilled people to choose from.

Manage risk

Don't stray too far from what you know -- unless you have bags of money to invest or a silent partner with big pockets.  And even then, don't spend any more on your new venture than you can afford to lose. Always run your dreams by your accountant first.

Get fit

Get fit and healthy if you aren't already. This is important.  Any new venture brings new kinds of stress and even though most boomers don't want to admit it, they aren't 20 anymore. You are in this for the long haul and an illness or injury caused in part because you aren't taking care of yourself is not something you need right now.

You have enough plates to spin!