DEAR HARRIETTE: My boyfriend (of six years) and I have been living together for three years. He is great, and I love living with him. He works at a suit store as the manager, and he enjoys what he does. However, recently he has been talking to one of his buddies about joining his startup tech company. When my boyfriend talks about this company, you can see his face light up with excitement, and I can tell this is the type of thing he is interested in.

I want to be there for him if he decides to join this startup, but at the same time, there is a voice in the back of my head saying, “I’m going to have to work double.” Our income used to be about equal and we split everything, but if he joins this tech startup, his income will be significantly lower.

Should my boyfriend and I be discussing this type of thing before he accepts the offer, or will it seem like I am discouraging him from following his dream? -- Half-Income Couple, New Orleans

DEAR HALF-INCOME COUPLE: The two of you should sit down and map out a strategy. Life always presents risks and options. You must figure out together if this option is worth the risk. Figure out how much money your boyfriend and you have saved and if you have enough to serve as a cushion while he is working to build the new business. Research the particular field that this company is in to learn how viable other companies like it have been.

Evaluate your own job, and determine whether you could upgrade based on time spent there or if you were to entertain a move to another company. Exhaust all possibilities in your discussion and research so that ultimately you make an informed decision that you both stand by.

DEAR HARRIETTE: I am a 24-year-old guy who graduated college a couple of years ago. I have a job in Philadelphia, but I am still living with my parents at home. I am so tired of commuting an hour by train every day into work. I need to decide whether I want to continue to commute to a job and company I love working for, or look for a job closer to home. If I choose to get a job outside of Philly, it might not be a better job, but it will save me the commute time and money. I’m not sure which option is better -- paying money to commute every day to a great job, or going through the process of finding another job that might not be so great, but will shorten my daily commute. -- Commuter Boy, Philadelphia

DEAR COMMUTER BOY: I have to ask you the obvious question: Why can’t you find another place to live? You are a grown man. You can look for housing with a roommate to keep the costs down. It shouldn’t be hard to find housing closer to your job. You can still visit your parents, but you do not have to live with them.

(Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to askharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.)

DEAR HARRIETTE: I want to visit my boyfriend in college for the weekend. My cheapest option is to catch either a bus or a train down and back. Even though this is the “cheapest” option, it is still pretty expensive, and out of my budget. My boyfriend knows that I don’t have money coming out of my ears and that I work hard for the money I do earn, yet he has not offered once to put some money toward the travel. I would usually not mind paying for expenses like this, but every time I travel to see him, I always end up paying.

Is there a way I could kindly ask my boyfriend to pay for a portion of my transportation? And if he says he can’t afford it either, should we just decide not to pay for transportation any longer, and wait until we are both home? -- Broke Girlfriend, Cincinnati

DEAR BROKE GIRLFRIEND: The red flag is waving right now! Beware of the precedent that you are setting. Since the visit to see your boyfriend is beneficial to the two of you, you both should be discussing how to afford it. The cost should not rest solely on you. It could be that your boyfriend is oblivious and just hasn’t thought about it. Or he could be manipulative. Either way, you must say something to him. Be direct. Tell him that you cannot afford to pay to visit him and that the two of you need to figure out options. Request that he share in the cost of the trip or that you agree to wait to see each other until he comes home. The way he responds to this will be important for you to evaluate. You don’t want to be with a partner who is selfish and insensitive.

DEAR HARRIETTE: My younger brother has recently moved in with me. I live in a two-bedroom apartment with my long-term boyfriend. Initially, when I agreed for my brother to move in, I thought it would be temporary, therefore I did not ask him to pay rent. It has now been almost two months, and he is still living in our spare bedroom. My boyfriend and I are getting pretty fed up with him lying around the house all day, and we want him to get a job. I keep bringing it up to him and threatening that we will kick him out if he does not get a job. It has gotten to the point where we are no longer speaking, but the situation hasn’t changed. I know that he is family, but what should my next step be? -- The Last Straw, Richmond, Virginia

DEAR THE LAST STRAW: Call a meeting with the three of you and lay down the rules. Tell your brother what your expectation had been for his stay at your home. Give him a deadline by which he either finds a job and starts contributing to the household finances or moves out. Stand as a united front with your boyfriend so that your brother understands that this is not an idle threat. It is real. When you reach the deadline date, be prepared to evict your brother if he has not lived up to the requirements.

(Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to askharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.)

DEAR HARRIETTE: I am a good student who studies hard and works to get good grades. I have recently been going through a lot in my personal life. It is affecting how much time and effort I put into my work. I failed an exam last week; it was the first exam I have ever failed, and I’m not sure if I should tell my parents. Part of me wants to keep it a secret because I know how disappointed they would be, but another part is telling me I should be honest with my parents. What do you think I should do? -- Worried Student, Philadelphia

DEAR WORRIED STUDENT: Keeping secrets is generally not a good idea, especially from your parents. It is their job to support you as you navigate your life and your academic journey. Clueing them in on your difficulties now may turn out to be a big help. They may be able to see ways in which you can rebalance your schedule -- or even just serve as a shoulder to cry on.

Additionally, you should speak to your teacher to find out what makeup work you can do. Ask if you can retake the exam. Sometimes this is possible. You must also evaluate your personal life to see what needs attention and what requires change. There should be a mental health counselor at school who can help you work through your difficulties and determine the best next steps.

DEAR HARRIETTE: I am a new mother of a baby boy. I wouldn’t consider myself an anxious or nervous parent, but I am struggling with the thought of leaving my child with a baby sitter or nanny. I know I need to start thinking about finding someone to watch my child, because I haven’t been able to have a social life and go out. I’m not sure how to approach the situation. Should I discuss it with my husband, my parents, a therapist, or someone else? Are there any baby steps I can start doing now to get me ready for when I leave my son for a few hours one night? -- Nervous New Mother, Washington, D.C.

DEAR NERVOUS NEW MOTHER: Talk to your husband about your concerns as well as your desire to balance being a mom with having some fun. Check in with him to see how he feels about a baby sitter or nanny. Think about the people in your life whom you trust. Do you know anyone who might be good to watch your baby? If not, ask friends for referrals. You can also go to an agency that is insured, which may help you feel less nervous.

In the beginning, it can be nerve-wracking to leave your baby with anyone. Feel free to check in regularly while you are away -- at first. Consider installing a nanny cam so that you can see what is happening at home when you are away. There are ways to be safe and free at the same time.

(Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to askharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.)