Timing is Critical in Starting Firm

Q: I have had a very successful run in high-tech, but now I would like start my own firm. What are some tips to think about? L.T., Toronto

A: Timing, timing, timing Those three words are key, just as "Location, location, location," is the adage when buying a house. Timing is critical in at least three ways:

PERSONAL TIMING Are you personally ready to make the leap? Think about personal finances. It will take longer than you think to generate the same level of personal cash flow you enjoy now. Cash flow really starts to hurt when you cannot cover the luxuries of your lifestyle, so remember this will impact your family, too. It will require a lot of emotion, time and energy while you are getting your company going.

PROFESSIONAL TIMING Think about your professional journey and what remains to be developed. Start by reading The E-Myth by Michael Gerber. He talks about the need for a clear understanding of the skills you have as an entrepreneur, and those you don't have.

MARKET TIMING We have all seen ideas that were just a bit too early or too late to market; both have inherent risks. Too early and you need a lot of capital and marketing to push forward your business idea. Too late and you need to have a well-defined niche, offer something truly unique, and the ability to move quickly toward high levels of efficiency.

SLEEP ON IT Assuming all three are green lights, there is one final thing to think about: sleep. Are you at peace with your decision? Are you comfortable with what you are doing? If you so, you will sleep well. I'll tell you now -- there won't be many hours for sleep, so they need to be good ones

Options For Bored Retirees

Q: My husband and I have been retired for three years. We are in our late fifties, we both have great pensions, but the retirement honeymoon is over. Both of us need to get out of the house. We're looking for a second career. How do we deal with this transition? C.K., Montreal

A: Think about a startup. Do you know which demographic is responsible for the fastest growth in successful startups? The 55-plus age group, according to a recent CIBC survey. The options for people of your experience, lifestyle and security-level are quite broad. That said, there are a few challenges:

You need to figure out how much time you want to give to work; whether you want to work professionally; and whether you enjoyed your work before.

Your key challenge will be answering the "what" question, before the "how." Many retirees quickly become disillusioned when they return to the workforce. You don't want to go through all the effort this entails only to be disappointed.

Have you had a particular dream or desire that you have not pursued but would like to? Paul Henderson once said, "Most professionals wish they would have taken more risk." Is there a risk you wish to take?

For your second career, you might consider looking for a hybrid -- maybe not exactly what you did, but a blend of your past career with some new angles.

Q: How do I deal with a leadership transition issue? My current boss said she was going to retire last year, but she has decided to stay one more year. I will be taking her position when she finally leaves and I have declined other options for the sake of this opportunity. Now I'm worried she may change her mind again. W.R., Edmonton

A: Ah, the Jean Chretien question: When are you leaving? Maybe you ought to speak with Paul Martin, the Prime Minister, instead of me. Knowing when to leave is a key question for any leader and anyone who aspires to step into that person's shoes. Waiting requires a fine balance between being loyal and taking action.

If your relationship is strong, I would suggest a face-to-face with your boss. Explain your dilemma and your expectations. I would also let her know that if she is planning to stay beyond another year that you will reconsider your decision to take over her role. Obviously, this should be represented as a reality rather than a threat. It is essential to be fair to both you and the organization.