What every small business needs for day-to-day problems

What do you do when you’ve gone to prison for driving on a suspended license? I do have three prior convictions for DUIs and a conviction for possession of narcotics. I’m partly disabled but I’ll do anything, just give me a day to work. I’ll even work for free the first day. What would you say to make me sound a bit better to an employer?
Um. I mean, other than saying you didn’t hurt anyone else (assuming you didn’t) I’m not sure what you can say. I’m rarely at a loss for advice. But I do believe most people deserve a second chance. I’ve personally hired many people who have made bad decisions, learned from it, paid the price and then got their lives back on track. They often turn out to be great employees because they appreciate that you took a shot with them. But what you’re describing is a lifetime of bad conduct, including very recently, so it’s going to be a very high hurdle to jump to get most prospective employers to take a chance on you. I think you need to commit to a new lifestyle first, and then do a full mea culpa, taking 100-percent responsibility and saying that you are finally turning your life around. Aim small, maybe for something such as bagging groceries or washing dishes, or start a handyman business, and work your way up from there. It’s never too late to turn a new page.

I run a small painting contractor business and I hire as many freelance painters as I need, depending on the workload. Many of these guys will take work only if they are paid in cash and I don’t withhold tax. How do I handle that from a legal perspective?
You already know that unreported income and paid wages violates various IRS regulations. And you also know that it is virtually impossible to run many such businesses if you had to follow every IRS regulation. So what’s a small business owner to do? You may not have a legal department but you do need a lawyer when you run any kind of business. Find one, and that person will help you carefully navigate the day-to-day realities of running a small business and the laws that govern them.

Gregory Giangrande is a chief human resources and communications officer in the media industry. E-mail your career questions to [email protected] Follow Greg on Twitter: @greggiangrande. His Go to Greg podcast series is available on iTunes.

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