Dear Helaine: My financial life feels extremely unbalanced, and I don’t know where to begin to fix it. Thanks to a divorce settlement many years ago, I bought a house in a popular summer community. It’s now worth $2 million, and I own it free and clear. My finances worked as long as my ex paid child support, but our daughter aged out of it, and I am slowly sinking in a very expensive boat.

I have $30,000 in debt, and I haven’t filed taxes in a few years. I work for myself, and while I earn enough to get by and maintain the home, I have no retirement accounts, no health insurance, and no ability to get a mortgage so I can take money out of the home. The older I get, the more challenging this all starts to feel.

I met a couple of older gentlemen, clearly successful and now retired, through a local program to help small business owners. Both suggested I sell the house, use about $1 million to buy a new, less-expensive one somewhere nearby where I can rent rooms out via Airbnb, and put $500,000 in an annuity for a guaranteed income. Everyone I ask hates the annuity idea, but how else can I stabilize my income? -- House Rich and Cash Poor

Dear House Rich and Cash Poor: There is only one way to move forward. That’s one step at a time. So where to begin?

You are going to have a very hard time getting your financial life organized as long as those taxes aren’t filed, so I would suggest calling an accountant as soon as you read this note and getting on the process of filing the taxes. The IRS will likely work out a payment plan with you, so you won’t need to come up with a lump sum for all the back taxes and penalties at once.

Second, you need to hope your health remains good and you suffer no accidents till the next Affordable Care Act insurance open enrollment period. As it stands right now, if something goes wrong, you could owe a lot of money to various hospitals and doctors.

As for the home -- where the tax money will come from and likely your retirement savings, too -- sell it. Don’t buy another large house. Purchase a small condo that you can afford and invest the difference. Airbnb is not a guaranteed income stream.

Next, all your friends are right: Don’t listen to random men who give you investment advice. An annuity is an extremely complicated, high-cost investment, one that locks up your money for a long period of time (sometimes permanently). The reason it gets pitched is because the people selling annuities make major commission money peddling them.

When you are ready, sit down with a financial adviser working to the fiduciary standard and come up with a plan. And while you are doing all this, work out how much you need to live on and not run up debt.

I know this is all tough, but it will get easier as you go on. The paralysis is part of the financial problem. As you push back on it, the pressure on you should release.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)

Hi, Helaine: I have stock in a family business my father left me when he passed. My sister, my two brothers and I own equal shares, a little more than half the business. The rest is owned by a few cousins who also inherited shares. I am no longer involved in the business, have no emotional attachment and could use the money.

I left 15 years ago and we all get along great -- better, actually, since I left the company. The shares used to pay dividends, but they changed the policy after I left. I recently asked my siblings if the company would be interested in buying my shares. I would rather the company buy them than just one or two siblings because my father always believed we should be equal. (My sister definitely can't afford it.)

My siblings are concerned that we currently own the majority of the stock, and if I sold the stock back to the company, that would no longer be true. I'm 55 and I'd like to settle this, but I don't want to look desperate. Any suggestions for how I can clear this up? -- Unwilling Shareholder

Dear Unwilling Shareholder: A firm conversation with all your siblings is in order here.

I'd tell your brothers and sisters you are ready to sell your shares, and you would prefer to do so in a way that no one is disadvantaged. Perhaps your two brothers who can afford to buy you out can lend your sister the money so she can do the same. Or perhaps you simply need to accept that you can't be responsible for everything, and make arrangements to sell the shares to any sibling who wants them. If none do, move on to your cousins. Or perhaps -- if the business can afford it -- they can vote to allow dividends once again, so that you are not under so much financial pressure that you feel you need to sell.

But one thing I want to make clear: You should not continue to damage your own finances in the name of family unity and solidarity. You are not acting desperate; you are simply being truthful and looking out for your own interests. There's nothing desperate or wrong about that.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)

Dear Helaine: My boyfriend of four years wants to get married and I'm hesitant. Part of it is that I'm in my late 40s, been married before and got taken in my divorce.

My ex had wealthy parents, and we were going to inherit one day, so we used my money for extra expenses like the down payment on our home and travel. I also took out the max in student loans because we figured we could pay them off when we inherited. Instead, we got divorced, and I ended up with my original down payment and all the student debt. Of course, this soured me on marriage.

So, my boyfriend. I earn $30,000 a year more than him, and I save diligently. He spends without thinking, doesn't plan for the future, and has no retirement or other savings. Neither of us has any debt, but I worry about combining money when our approach to finances differs so, and, of course, I worry about the financial impact of another divorce. So I've said no to marriage, but I know he still really wants to.

I would love some advice on how to approach our differences. Does it make any sense to be in a relationship with someone whose values around money are so different? -- Once Burned

Dear Once Burned: You learned the hard lesson that funds are not your funds until they are in your bank account. You've now taken that lesson to heart -- maybe too much to heart. So here is my two cents: No two people are ever going to agree in full about how to approach their finances. Your wannabe husband isn't so much irresponsible with money -- as you point out, he doesn't have debt -- as he's not fully an adult about how to approach it. It's a subtle distinction, but an important one. It means there is hope you can work this out.

You are most certainly not out of line to say you would not marry him without evidence he can save money, and do so for a period of time. Perhaps give him some guidelines, such as, "I would like to see you contribute 5 percent of your salary for a year to a 401(k) before I consider marriage."

But that's IF you want to marry again. There's no reason to do so simply because he would prefer it. You need to want it as well. And there I can't help you. Only you can answer that question.

(To ask Helaine a question, email her at askhelaine@gmail.com.)

(EDITORS: For editorial questions, please contact Sue Roush at sroush@amuniversal.com)