QUESTION: John recently took a job that requires expenses of $5,000 a month. His company told him to get a credit card to cover things, and that he would be reimbursed, but John is trying to get out of debt and doesn’t like the idea. He asks Dave what he should do.

ANSWER: When you talk about the cost of doing business, it’s the responsibility of the company, not the employee, to pay expenses. If I send someone on the road to make money for my company, I pay the bills. It doesn’t matter if you’re talking about hotel rooms, airfare, or rental cars, those are my expenses. If it’s someone who travels a lot, we give them a company debit card. If it’s just an occasional thing, we’ll give them money out of petty cash.

It’s a mystery to me how some segments of corporate America have sold their employees on the idea of being the company bank. Ultimately, the decision is yours. If you don’t mind covering your company’s expenses and getting reimbursed, but you don’t want to go into debt, you’ll have to save and build up a $5,000 business expense fund. This fund should be in a separate checking account, and it should be used only for business expenses. Anything that’s spent from this account should be replaced immediately when they reimburse you.

Personally, I think this is an unprofessional way to run a business. But if you like your job, and want to stay without taking on any more debt, the good news is you’ll only have to fill up your expense account one time.

QUESTION: Krista is being considered for a sales manager’s position. She has sent a couple of follow-up emails in the last few weeks, but she’s unsure of what to do now. Dave advises Krista to put her sales skills to work this time.

ANSWER: How about treating it like a sales call? If you’re on a sales call, and the customer needs to perform some due diligence before deciding, a smart salesperson will ask to schedule a follow-up. You want an appointment of sorts — a time frame — so you’ll know when to follow up without being pushy.

In this situation, I would recommend sending another email. You want to walk right up to that fine line that separates bold from obnoxious, because that’s one of things a good sales manager should be able to do. Respectfully tell them you understand the decision-making process takes time, but you need to know when you can expect an answer.

Use the idea that you’re a great sales person, and you’re treating this as a professional sales call. And don’t be afraid to have a little fun with it. If you’re still under consideration, that means they like you. You could even hint at the fact they don’t want to hire a sales manager who doesn’t know how to follow up.

QUESTION: Steve makes $25,000 a year at his day job, and he has side jobs as a personal trainer and a DJ. He has paid off almost all his debts, and he asks Dave how to tell when he’s ready to leave his regular job and concentrate on the other two.

ANSWER: I always tell people to first get to a point where their side hustle is generating almost as much money as their day job. I want the boat pulled as close to the dock as you can get it, so that when you make the jump from the dock to the boat you don’t hit the water.

In your case, I would want the $10,000 you earn from personal training to look more like $20,000. When you reach that level, combined with what you’re making as a DJ, it would create a pretty safe situation for you to quit your day job.

Maybe you could cheat a little on the personal trainer money, because you’re making as much or more as a DJ as you are in your day job. Otherwise, you’re giving up $25,000 for $10,000 and only hoping the personal training gig will grow. That’s not a good idea. I’d like to see that hope proven a little bit more before you walk away from a day job.

QUESTION: Jeff took a new job about four weeks ago. Just the other day, he was recruited by another company for a position paying twice what he makes now. Jeff didn’t sign a contract stipulating how long he would work for his current company, but he values integrity and wants to handle things well and do the right thing. Dave gives him some advice for handling this uncomfortable situation.

ANSWER: I try to put other people’s shoes on. Let’s pretend you own the company, and you just hired a young guy. Then, somebody offered him double and he walked into your office and said that. I can tell you what would happen here. I’d tell him to take it, because I would. And I’m not going to double his income that quickly.

Now, if you’ve got an unreasonable person working there, they may not say that. They may try to put some kind of guilt trip on you or something like that. But truthfully, if an organization cares about its team members, and one of those has the ability to double their income and they’re not breaking a promise in the process, then it’s a reasonable thing for you to take the job.

I would probably want to walk into a leader or supervisor’s office and just say that. Just let them know that you feel awful about the situation, and tell them you know they’re good people and they wouldn’t expect you to stay if you had the opportunity to make double what you’re making there. Let them know you had no intention of being misleading to them when you came in and that you’ll do everything you can to make the transition as easy as possible.

But I think you take the job. Just talk about the awkwardness out loud, and remember that their reaction may be more about them than anything else. But I mean, as the boss or owner of the company, how am I ever going to feel right about that if I ask you to stay?

That’s how I would handle it. All I’m doing there is treating other people the way I like to be treated—as an employer or an employee. I would just walk in there and tell the truth. Just make dadgum sure you’ve got the other one tied up before you do that.