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As a business owner, you know what it’s like to lie awake at 2 a.m. Maybe it has happened when you are excited and full of new ideas for your business. More often, it’s because you are worried about issues you will face the next day. Sometimes, it’s because you just woke up with the solution to a problem. I’ve experienced all those emotions about my businesses over the years. Awake at 2 o’clock? is where I share them with you, and hopefully help with answers that will let you sleep.
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Tag Archives: employees
The Extinction of the Summer Job
I’ve read several articles of late discussing the decline in the number of older high school and college students that take jobs for the summer. Each of these reflected on how summer employment taught millions of Americans their first work habits. Around … Continue reading
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Ageing Boomer Entrepreneurs: Fearful or Smart?
Do we become more cautious with age? Startups are usually associated with younger entrepreneurs. By the time they reach their 50s or 60s business owners tend to tackle fewer big new ideas. Those that do tend to be successful enough that they … Continue reading
Posted in Building Value, Entrepreneurship, Exit Planning, Exit Strategies, Life After, Thoughts and Opinions
Tagged Baby Boomers, Boomer Bust, business ownership, business planning, business strategy, economy, employees, entrepreneurs, entrepreneurship, exit planning, exit strategies, leadership, management, new business, small business, small business advice, startups
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One Response to Ageing Boomer Entrepreneurs: Fearful or Smart?
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Experience is what you get when you don’t get what you want.” or “Good decisions come from experience. Experience comes from bad decisions.”
I agree with both of these. I really enjoy your blogs! I was forced into inventing a “new self employed start up” at 62. I have no regrets but with my “experience is what you get when you don’t get what you want” is an ongoing goal as well.
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Culture Counts!
Small businesses can’t compete with large corporations on salary and benefits. I’m not being unduly cynical, it’s just a fact. The top 1/10 of 1% in US household incomes start at $1.9 million annually. Of all those in that rarefied … Continue reading
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When Supervisors Become Managers
Any promotion means more responsibility. Few steps require as big a leap as the transition from supervisor to manager. Each step up the ladder involves a change in tasks, but an employee’s first managerial position necessitates a change in thinking; one which isn’t … Continue reading
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You Can Go This Far, but No Further
When someone starts their first company (especially a technician as defined in my book Hunting in a Farmer’s World) he or she is usually the sole key employee. She (I’ll use one pronoun for readability) does the hands-on work of … Continue reading






Hi John,
Whoa, this describes the situation exactly (except I don’t know of any “middle class” folks that can afford summers in Europe)! As Chief Moderator at BizSugar, I feel your article hits home to small business owners the fact that most young people — not millennials, but generation Z, those who are about ages 15 through about 18–will be entering the job market with far, far less practical experience than even the millennials, let alone Gen X or the boomers, and this message may really deter them from giving these young folks a chance. As minimum wage jobs go up to provide underemployed adults with a means of providing for their families, perhaps it’s a good idea for small business owners to re-create those summer jobs of the past, by hiring a kid to scan some documents, run errands, do a little of this and of that and above all, get used to talking to customers and dealing with people. As a parent, I’d like to see this, but from the SMB’s perspective, they might not have the extra cash lying around after they pay the grownups.
Hmm….food for thought.
Your point is well made, Heather. A new generation is coming into the workplace with less work experience than any before. It will be interesting, to say the least. Thanks for your input.