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10 Ways to Generate Extra Cash in Retirement

10 Ways to Generate Extra Cash in Retirement

It's no secret that Americans are largely not financially prepared for retirement. Survey after survey shows how little is saved and that many are pushing back retirement, some as far back as 85. It's not your father's retirement, and it may in fact be no retirement at all.

But that said, there are ways to beat the statistics. Even if you haven't saved that fortune you hoped, with a bit of creativity you can come up with a way to supplement your retirement stash. You'll most certainly will need to. “A retiree that retires today will need more to live on in 10 to 20 years because of inflation,” says Jeff Sica, president and chief investment officer of Sica Wealth Management.

Here are a few ideas to get you started.

Tweak your portfolio

For those that have highly appreciated securities that may not be paying a dividend, consider using a Charitable Remainder Trust (CRT). It can help reduce the capital gains tax, as well as convert the asset into a steady stream of income, says Jonathan Gassman, director of tax and wealth management at Gassman & Golodny, a tax and accounting firm..

Then too, those over 59 ½ and looking to generate income could consider a partial conversion of their Traditional IRA assets to a Roth IRA – and then purchase an annuity with a lifetime income rider after the conversion. “Doing this allows you to essentially pre-pay tax on the amounts converted at today's tax rates, providing peace of mind because the income will be tax free when it is withdrawn. Consult with a tax advisor to make sure it's a smart move for your situation,” says Judy Ravenna, senior vice president with SunTrust Investment Services.

Get entrepreneurial

Turn your hobby into a business. For example, if you own a boat, think about getting your captain's license for chartering. “My uncle used to build lobster pots and sell them for actual usage or it made a great table for the living room,” says Gassman.

Put yourself out there as a dog walker, you'll get paid and get much needed exercise too. Make yourself available for driving to and picking up people from the airport, adds Gassman. If you love gardening anyway, why not start growing goods for others and see if you can sell them at a nearby farmer's market.


You have a ton of stuff that has accumulated over the years. Some of it is junk, but many will be treasure to someone else. Have a series of garage sales. Sort through your belongings and get rid of what you don't need. “Not only will you get cash, but you'll free up storage too,” points out Frank Festi, Jr., a certified financial planner and principal with Rea & Associates, an accounting firm.

Rethink your house

What do you need that big house for? The money you'll save by moving to smaller digs will free up monthly cash that was going toward hefty heating and air conditioning bills, not to mention maintenance. This move can also be a plus tax-wise. “You can sell your home for more than you paid for it and not have to pay capital gains tax,” explains Festi. The amount excluded is $250,000, for an individual, or $500,000 for a married couple.

“If you're hurting for cash you may want to consider a reverse mortgage. If you're not worried about leaving an inheritance, this is a solid option,” he adds.

Review your life insurance

The policy you have today may no longer be applicable. Check with your advisor to be sure. You may be able to cash in on a death benefit if it's no longer needed. However, you'll have to pay tax on it. Another option would be to do a tax-free exchange into an annuity policy and have cash flow for the rest of your life, says Festi.


Not only will you be occupying your time and doing some good in the world, when you're volunteering, you're not spending. “Find ways to help further causes you believe in. This is a great replacement for those more expensive hobbies,” says Festi.

Make free your favorite word

If you have never paid much attention to BOGO, (buy one get one free), do so. Stock up and use sparingly and you'll find you shop less and therefore spend less. Attend free events. There are a lot of free events in most every community. Watch for those concerts, lectures, and other events that you can take in for nothing, yet still have a good time.

Work part time

Any dollar you can get from somewhere other than your retirement portfolio is a plus. You're not looking to make a killing, but just to give yourself a little breathing room. Make it sweeter by seeking fulfilling positions that will also put money in your pocket. “Work as a substitute teacher at a public or private school, serve as a greeter at a restaurant where your family and friends often gather, or share your passion for books by working a few hours at a neighborhood book store,” suggests Ravenna. You could also serve yourself up as a tutor. If you don't want to commit to a steady part-time gig, consider temping.

Speak up

Sure many times businesses are big on promoting their senior discounts, but not always. Some kind of grudgingly offer them, so unless you ask, they aren't going to go out of their way to let you know it's available. Don't be shy. Always ask whether there's a discount for seniors. A few dollars here, a few dollars there, and soon you're talking real savings.

Stay healthy

No one can completely control their health, but do the right thing for your body and you stand a better chance that it will do well by you. Exercise, eat like your mother told you, and maybe you can keep illness to a minimum, and that for sure is one the single best ways you can improve your cash flow.

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Anonymous/ Paoli
Anonymous/ Paoli   |     |   Comment #2
Interesting article, Sheryl but my concern about working after receiving Social Security is that one has to be penalized for any amounts earned.  Can you explain how that works and how much you have to give up of SS benefits for amount earned?    Is that still being done to people who earn SS and try to work to add to income?  Thanks.
Anonymous   |     |   Comment #4
Sheryl:  Since I didn't want to join the other turnips on the truck per "koisushi", I googled up the info on working and receiving SS.  One can earn quite a bit more than it was years ago when I first checked.  However, that does make the AGI higher and we end up paying more taxes on SS income so I think when I figured it all out, I decided working and paying more to the gov was not the way to go for us then.  Now that interest rates are so low on savings, I may have to do some refiguring.  Just ignore my earlier request. Thanks.
Anonymous   |     |   Comment #6
#4   What are you trying to figure out?  Be more specific.
AnonymousPaoli   |     |   Comment #8
#6  I figured it out.  If you google you can find out how much one can earn by working after receiving social security. If you earn more than given figure you can lose a certain part of your benefits or extra amount over this earned.  If Sheryl was recommending we get some type of payable work after retiring (if we need extra income) I wondered why she did not mention the part about the impact to any social security people are receiving and how the extra income can cause us to pay more taxes on social security.  Sorry if I did not make myself clear.

#7 Why don't you stop trying to be the comic of the Blog and instead add something "on-topic" to the thread.  Maybe you then actually will post something that won't get deleted! 
Anonymous   |     |   Comment #5
Again, Sheryl your ideas are fine only on paper. When it comes to reality, it can not be implemented.
For example your idea to stash your money in “Charitable Remainder Trust”, it means to part from your money for good and nobody guarantees that the organization will exists after you give them your money nor any state will guarantee your principle.

Furthermore, you are quoting people who like to make enormous commission on flipping your money and they could care less if you lose some of your principle.

You idea of “Get entrepreneurial” is laughable, I mean to become a captain or a dog walker or sell my so called junk items, come on, stop pulling our legs, suggest something meaningful that makes real money not pocket change or one time only.

I work all my life to relax and enjoy the comfort of my house, going into smaller house will not save you much money as you think. I own 2 Bed 2 Bath house in a mountain resort and I own my main house 4 Bed 4 Bath in the city and I can tell you this:
When compared the 2 properties, the difference in expenses is just $500 per year when subtracted the insurance, property taxes and upkeep and repairs. Giving away the comfort for just few hundred dollars a year makes no sense.

How can volunteering make me money the title of this article is:
“10 Ways to Generate Extra Cash in Retirement”

You said to work as part time teacher or a substitute teacher, I’m already registered as such in my local school district, but never got called for duty in 3 years because I know that there are at least 50 other persons registered as such, plus most of the retired teachers are already registered with the board of education as substitutes.
Dana   |     |   Comment #9
To #2. Yes; you CAN still earn money while collectins Social Security. The amont you can earn is based upon factors including your age and the reason you are gettting SS income (such as disability or regular retirement). Your benefits can be reduced or elimnated if these limits are exceeded. For more specific information concerning these conditions; please contact you local Socia l Security office or visit www.ssa.gov. 
CraigPD   |     |   Comment #11
"I wondered why she did not mention the part about the impact to any social security people are receiving and how the extra income can cause us to pay more taxes on social security."

Probably because relevant IRS rules have been in place for 30 years and this article provides an overview - not step-by-step instructions, otherwise readily available from many sources.  Or were you expecting any additional earned income to be tax-exempt?  More entitlement mentality that has us up "stink" creek.
Anonymous   |     |   Comment #12
#11 .  After I asked the question, I did do my own research and got my answers.  What has this to do with "entitlement" mentality?  Please direct your anger to the right people.  I am NOT looking for entitlements and I don't see how my post could make you think that.  I guess you just needed to vent.  Have at it!
darkdreamer4u   |     |   Comment #13
Easy fellows - no need to get your knickers in a twist...
Anonymous   |     |   Comment #14
If you want to generate more income in retirement push your representatives to STOP all the government free programs to the long term unemployed people who are ABLE to work but choose to take free hand outs.  Most people can find some type of a job, but choose not to work when the handouts exceed what they can make working.  Where is there self pride?

PS.  I don't consider Social Security or Medicare as handouts.  We worked for it..
Anonymous   |     |   Comment #15
#14  Maybe there is no self pride in these unemployed people because it is too easy for them to get the checks.  Many years ago when I used to work and became unemployed, I remember I "had" to go each week with a list of employers I had interviewed with and had to be able to show why I was turned down for the job.  If I didn't have my list to show my case worker, I could not be eligible for my check.  Is it still done this way?  How do all these people prove they really can't get jobs now?  Are their checks just sent to them weekly without proof of a job search?  If it is, then the government is training them to be a society of "give mes".  So many states are already having to file for bankruptcy that I can't believe they don't have stricter rules for getting unemployment. 
Anonymous   |     |   Comment #16
In today's environment most companies will only accept email or internet applications.  Most companies never reply "yes" or "no".  That makes it very easy to reply to the unemployment people that you actively looked for a job.  Just keep updating your list.  Our country is becoming a bunch of "free loaders" at a early age.
Anonymous   |     |   Comment #17
Goodness #16:  I had no idea that's how it was done!  No wonder they can keep getting benefits for so long!  The computer is certainly their friend!  How times have changed.  No wonder our country is bankrupt!
Anonymous   |     |   Comment #19
 To Anonymous - #17,

That is only one aspect of the free benefits, just look what Obama did few days ago.
By a Presidential decree he sent HHSA (Sibelius) ordering her to stop the work requirement for the people on welfare and by that he officially by passed the Congress and made cradle to grave welfare nation.
Who will pay for it:
 First with borrowed money from China and when that will stop, he will start printing money like there is no tomorrow.
God bless us!

Nice observation #5
AnonymousPaoli   |     |   Comment #20
#19  I have news for you.  If voters give Obama a second term to continue his actions, "there will be NO tomorrow" for our country.  So many people have already learned how to "game" the welfare system and now he has given them the winning chips!   Just because someone is poor does not mean they are too sick to work.  It used to be that poor people wanted to find a way out of welfare now it is a crown to wear it seems.  What a sad day for our country!
Anonymous   |     |   Comment #21
WE are paying for it with prolonged zero interest income.

Thank you Obama and and his lapdog bernacke
Anonymous   |     |   Comment #22
I don't want to vote for Obama, but Romey isn't any better.  It's a catch 22.  Don't we have anyone in the US worthly of being the President?
Paoli2   |     |   Comment #23
#22  I just finished writing a letter to Romney.  He needs to get his act together and show us he is worth our vote.  "He" is still trainable and is for capitalism so I would rather have him than someone I have already seen tear our system apart.  He needs to start showing he is presidential material.  I just could not live with my conscience if I gave Obama a second term to finish his destruction of our system and I sure hope other Americans feel the same way. 
darkdreamer4u   |     |   Comment #24
You guys are killing me with all your talk about Obama destroying the system. This is utter BS - he's only doing what most other developed nations have implemented ages ago, i.e., a universal health care system and trying to undo the damage that Bush's cronies afflicted with their corruption (Haliburton anybody?) and misguided ruinously EXPENSIVE wars!

With the GOP in the driver's seat, there would be NO system at all because they would dismantled it (if they could) or at the least they would weaken it to a degree that it would be dysfunctional (which would then provide them more amunitiion to privatize aka abolish it) - see where you get your Social Security checks then!
Anonymous   |     |   Comment #25
Blah, blah, blah.  BOTH parties are equally guilty.  All this financial turmoil and instability in our country didn't happen overnight, nor within just the last three years or so.  The real sad part is that I don't see any end in sight no matter who wins future elections.
Anonymous   |     |   Comment #26
To darkdreamer4u - #24,
Have you looked at the cost for the Obama care, it will cost over $1 Trillion per year to run it when fully implemented and who will pay for it?
Are you willing to lower your standard of living by giving most of your paycheck and not earned income to the Government?
Think long term, not just for today and tomorrow, this will change our life style for worst.
And who will benefit from it, mostly the people who already are in the free for all welfare on the expense of the young and retired who will pay in new taxes and diminished Medicare coverage.
Anonymous   |     |   Comment #28
#26  I get so tired of people throwing everyone who needs healthcare insurance into the pot with welfare recipients!   I have a DD who lost her job quite some time ago and has a chronic medical problem.  Once her COBRA (that we are paying for and is costly) ends, I will have to scourge around for another plan for her and hope it will be affordable and her doctors will be in-network.  This causes me great concern not knowing where to find a new plan.  SHE is not a welfare or unemployment recipient!  YOU are not paying a penny to help my DD so don't throw everyone into the same pot.  However, that doesn't mean she doesn't need healthcare insurance.  Obamacare had a lot of good in it but it is too costly to taxpayers and our deficit.  But we DO need affordable healthcare insurance in the US!
Anonymous   |     |   Comment #27
Please, the Big "O" has not done anything, but drive our ecnonomy into the tank.  He has had four years to get his act together and nothing to show for it.  I'm willing to give Romney a shot to turn this economy around. 
Anonymous   |     |   Comment #34
Can't we all just get along? :)
darkdreamer4u   |     |   Comment #36
To Anonymous - #26,

It would be easy to pay for those costs by, e.g., cutting defense spending - we spend the most money of all countries, more than what's the number? The next 10 nations combined? Whatever, it's too much!; by lifting the cap on social security tax, i.e., no more paying nothing for income above $110,100 - every penny should be taxable for social security which would take pressure off the rest of the finances; by closing many loopholes through which the rich can avoid tax - there are many ways to do it.
Paoli2   |     |   Comment #37
Ditto #34  "PAX"  to all !
Pablo Savin
Pablo Savin   |     |   Comment #38
Great comments. Affordable health care is needed. There will be those who will have to suffer to change the system. Insurance costs are so high in some part because hospitals are forced to treat people who cannot or will not pay for service. Why should hospitals treat those who cannot pay? I know it sounds cold, but what would food cost if only half the people paid for it and there were no food stamps? This is reality. I have friends who have kids, no health insurance. But they have nice cars, go on vacations, have three tv's etc. Get the picture. Oh ya, there is no self pride. The bank made you get that big loan, those credit cards kept coming in the mail, I couldn't help it. On and on, and Obama panders to this type of thinking. Sorry for the rambling. By the way Ken, thanks for everything, your site has helped me to be on track to retire at 51.
Anonymous   |     |   Comment #39
How about selling sperm for extra income? Oh wait, I forgot about the average age here. Nevermind. :)
Anonymous   |     |   Comment #42
Does Ms Ravenna know what year it is?  Her suggestions about working in a neighborhood bookstore or substitute teaching are, to say the least, outdated.  In case she hasn't noticed, neighborhood bookstores are rare and in most that remain the owners are lucky enough they make enough to support themselves much less pay any additional employees. Most school districts have an overbundance of qualified teachers, many of whom are being laid off,  so it is doubtful they are going to hire anyone else. 

If your going to seek information, please seek it from someone who has some connection to reality.
Anonymous   |     |   Comment #43
Does Anony #42 know who Ms. Ravenna is?  The article was written by Sheryl Nash afaik.