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Inflexible leave policy ‘simply unacceptable’

Dear J.T. & Dale: My superior doesn’t like to approve leave (whether short or long) until the day before the leave itself. The reason given is that he would not know what will happen in the future and at the point when I take leave, the company might be in need of me. This makes it almost impossible to plan a holiday, especially to book cheap flights. – Omar

DALE: Such a policy, if rigidly enforced, is simply unacceptable. There are occasions where you see it – for instance, a startup where everyone is working furiously toward a launch date or in retail during the holiday season – but only for specified periods of time. However, in general, employees with a life would leave such a company, and so should you. My only hesitation is the word “like” in your first sentence – does he whine about it but still make exceptions?

J.T.: That’s why I would set a meeting with him and let him know about a trip you are hoping to plan and the need for you to book the flights early enough to make them affordable. Ask him what you can put in place or do in advance to go on this trip since you will not be able to cancel. Hopefully he will give you assurances. If not, you can go to HR or to upper management and tell them what is happening and see what advice they offer. However, please know your boss will likely be upset that you went around him and may take it out on you.

DALE: I’d only do that if you have a good job lined up, and, if so, why bother?

J.T.: That’s where I was headed – to suggest you look for a new job and leave. Any vacation policy that doesn’t let you plan a vacation isn’t a fair policy. There are other companies out there that will understand your desire to book in advance and want you to go on your vacation because they know it will create a happier, more loyal employee!

Dear J.T. & Dale: I just graduated culinary school and I want to start a business helping people shop for food and make healthy meals. However, I need a full-time job to support myself. That leaves no time for the business. What should I do? – Carli

J.T.: You aren’t alone. Most people who have business ideas lack the time they want to work on them. My advice is to dedicate a certain amount of hours of your free time each week to developing the business. You might want to take a course on starting a small service business. I’d also suggest finding a mentor. There are also some great free resources like SCORE, which connects you with retired business owners for mentoring. Simply put, you need to see the path to getting this business going on limited time and resources. The answer is in talking to people who can say “been there, done that” as a way to remove your own mental roadblocks and get you on the path to success!

DALE: All good advice, but here’s something even better: The undertaking you’re describing would make an ideal business to evolve into. Here’s an IBP, an Important Business Principle: You’re not in business when you have a company name; you’re not in business when you have a spreadsheet, or even when you have an office or shop with your name on it. No, you’re in business when you have a customer. Said another way, just start. Sign up a friend or relative and begin. That drives you straight up the learning curve. You’ll eventually cut back on your current job in order to accommodate the new customers you’re attracting, and then if all goes well, the new business simply replaces your old career. Some people would be frightened of such an evolution, knowing that they’d be working two jobs for a while. But that’s your startup capital – you’re financing the new business with your effort, rather than your savings or your parents’ savings. And the new business will be healthier for it.

Jeanine “J.T.” Tanner O’Donnell is a career coach and the founder of the leading career site Dale Dauten is founder of The Innovators’ Lab. Please visit them at, where you can send questions via email, or write to them in care of King Features Syndicate, 300 W. 57th St, 15th Fl, New York, 628 Virginia Dr., Orlando, FL 32803. (c) 2019 by King Features Syndicate, Inc.