Category Archives: Health Insurance

Can You “Job Stack” to Make This Work?

By job stacking, I am simply talking about having more than one job at a time.   For someone creating a semi-retired life,  working for a period of time then taking a period of time not working at all, job stacking may provide a means to finance their lifestyle.

I am only advocating this if you do it for short periods of time such as a season, and the objective is to be able to put money away for your time off.  If doubling up work still leaves you short, then you aren’t ready for a semi-retired lifestyle yet.

The trick to this is finding the combination that works for you, and managing the variables.


If you are working more than one job as an employee, communicating effectively with your managers at each position is vital.   Tell them outright what you are doing, so they understand your scheduling issues.

If you can only work certain hours, be up front about this in the interview.  There is nothing new about this – students do it all the time, and employers work with them around class and testing situations.

Seek Flexibility

You are more likely to find someone who will work with you in a locally run small business than with a big company that has rigid work and absence rules.

The hardest situations are the ones where you bid your schedule by seniority or can be “called in” or retained if someone doesn’t show or gets sick.  This is particularly tricky in any type of unionized environment, as the junior person (last hired) gets the least control of their schedule.

Combine Job Types

If your primary seasonal or contract job is like this, then your best option to stack is going to be something that you can do completely on your own time such as freelance writing, data entry, or online sales.

This is an ideal situation if you have an artistic or creative side business of your own. Spend some of your time creating, and other of it seeking both local and online distribution outlets.   If you take photos, look for locally run shops and cafes where you could display for sale.  If you write, is there a local newspaper that pays by the article?

This may not be the time to be picky and turn down work that is below your skill level.  If you can get $20 for something that takes you 30 minutes to produce, it may be worth it.   Check out for this.

Seek Non-Overlapping Businesses

For example, if you are doing substitute teaching, then you could also do evening work in a restaurant that’s only open for dinner.  If you are waiting tables in a breakfast/lunch place that closes at 2pm, you could do some type of direct selling in the early evenings.

The challenge with all of these options is managing your health and fatigue levels.   Particularly if you wind up working evenings late and have to show early to the other job.  You will wind up sleeping a few hours at night, and a nap in the daytime.  Over time, your body may revolt on you.

Also, keep in mind that is a temporary means to end.  It’s not ideal, but it might create a way to finance the goal of taking 8 – 12 weeks away from work.

Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

Alternate Career Life: Anchor in Place or Travel for Work?

As you ponder, daydream, or make serious plans about living a semi-retired life, give serious thought to this one piece first.  Keep in mind, if your initial choices don’t work, you can always change them.

Are you planning a mobile, traveling, different-places life?  Or, do you want to have an anchor-in-place approach and build all your opportunities around, from, and in that place?

Stay-in-Place Considerations
  • Do you live now where you want to be when you semi-retire?
  • What kind of housing do you want to have or have now?
  • Are you going to need something bigger or smaller, or is what you have just right?
  • Is your housing also part of your income source?
  • Is renting your home, or doing home exchange an option during your “off” time periods?
  • Is commuting to/from work an issue?
  • Costs – can you live this life with your current housing and expenses?
  • Is there employment where you are anchored?  Particularly seasonal, temporary, or contract so that you can take a few weeks or months break when you want.
  • Or, will you need to start a business of some kind?   If so, I highly recommend Barbara Winter’s book  Making a Living without a Job.
Traveling Life Considerations
  • Well, where ARE you going to live?  Keep in mind that many seasonal tourism jobs provide housing.
  • That said, what are you going to do with your belongings that aren’t traveling with you?
  • Can you afford multiple residences?
  • Are you going to keep a primary residence somewhere as a base of operations?  If so, where?  (Think about tax implications)
  • If not, what are you going to use for a permanent legal address?
  • Is portable something that would work for you – RV, camper, tiny house?
  • How are you going to get around?  (If you have an RV, you won’t want to take it to the store for a loaf of bread…)
  • What work are you going to do – same type job just floating with the seasons to different locations?   Or, a different job every season?  For example, I have a recurring summer position where I live now, but plan to travel or live in other places during the Fall and Winter once I get my youngest child launched.
  • You will need to figure out your banking (MUCH easier than it used to be), and bill-paying.  Where will your bills be delivered?
  • Communications services – cell phone, satellite, etc?

Note that these questions are appropriate and may affect your choices whether you are an individual going his or her own way, a couple who plan on doing this together, or even a couple where only one of you wants this type of employment.

Everything is negotiable when you are calling the shots.  That’s the point.

Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

Health Insurance for Seasonal Workers – Bridge Policies

As always, let me disclaim that I am NOT a health insurance agent or expert.  I am just sharing what I have learned and recommending you consult a professional.  Without a doubt, I do recommend taking the time to really educate yourself about your health insurance options if you are buying your policy independently.

I HAD heard of bridge policies – designed to act as a gap between loss of coverage for whatever reason and the next opportunity to enroll in “Obamacare.”   Going forward, I’ll use the official abbreviation of ACA for the Affordable Care Act.  These policies are NON-ACA compliant.

That means they HAVE exclusions for pre-existing conditions.

It also means they are substantially….SUBSTANTIALLY less expensive.

Here is the kicker, and what I did NOT know.   You can buy bridge policies as an ongoing method of insurance. 

As long as you do NOT have one of the pre-existing conditions that would exclude you, such as a heart condition, cancer, etc, you are allowed to just purchase these types of policies, instead of ACA compliant ones.  There are a couple “gotchas” that I want you to be aware of:

1)    Talk to an Independent Health Insurance Agent

The “Navigators” that are part of the ACA process cannot talk to you or really give you guidance about health insurance in general.  They can only talk about differences between their ACA-compliant policies.  Ask your insurance agent if bridge policies would be an option for you.

2)     Timing Matters

Bridge policies are for a specific period of time, up to 12 months.   If you develop an exclusionary condition while covered, you will not be able to get another bridge policy when it ends.   You can only sign up for ACA during open-enrollment (unless you have an exemption like losing a job).  So, it might be wise to time your policy end date during open-enrollment.  Ask your insurance agent.

3)    There IS a penalty

There IS a tax penalty for choosing this option.   Talk to your accountant.   For my family, the combined cost of the penalty AND the bridge policy was still considerably less than the premium for an ACA compliant policy.

4)    Stay Healthy

Without a doubt, the key to using these policies is being healthy.   If you already have an exclusionary condition, then most likely they won’t work for you.   But if you can stay healthy, bridge policies may be an affordable alternative.

Talk to an Insurance professional.

I recently read that one thirty-minute walk per day can make an incredible difference in your overall health.  See you on the trail.


Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

Books, Anyone? (Possible Dream Job Alert!)

Good Morning!

Every once in a while I come across a job posting and think, “This is someone’s PERFECT semi-retired life.”

Somewhat predictably, this position is in travel/tourism – one of the three  categories I’ve previously tagged as having seasonal/contract/temporary/part-year positions available.  (Teaching and Taxes are the other two.)

But, if cruising ships and reading set your heart aflutter, check out this position with Holland America as a ship Librarian:

Tracking Code
Job Description
Do you have a fun, independent and outgoing personality who loves to read and be in a library? Are you the person your friends and family come to with tech issues with their iPad, Android, Windows phone? Then a job as Librarian onboard a Holland America ship might be the perfect job for you.
Required Skills
  • Responsible for the operation, organization and appearance of the Explorations Café.
  • Checks in/out books, DVDs and related materials.
  • Responsible for organizing books, restocking shelves, maintain board games, puzzles, crossword pads, and newspapers for guests. Manages the replacement of lost and missing items.
  • First line of support and guidance for all guest Internet related matters.
  • Assist guests with Internet package to help improve revenue onboard.
  • Complies with all company operational procedures.
  • Successfully completes all required training programs.
  • Performs ship’s safety functions as required.
Required Experience
  • Previous hospitality or guest service experience.
  • Strong socializing skills.
  • Experience with basic help desk services.
  • Possesses an interest in literature.
  • Ability to relocate, live and work onboard with coworkers for 6 months.
Position Type
Here’s the Link to the Posting
Sigh…makes me want to curl up with a good book and a cup of tea.
Bon voyage!

Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

Why the “Gig” Economy Works for Semi-Retirees

Ever heard of the “Gig” Economy?

In a nutshell, it’s a workforce that goes from one work “gig” to another, getting paid above or under the table.  ( “freelancing” is a variation on this)  Although its origins are musical, it has come to define independent contracting in the workplace. In a recent  article, Dave Ashton of SnapCar made an argument for replacing certain types of traditional employees with contractors.  Make no mistake, he takes a controversial political position, more understandable perhaps when you recognize that it is based on the French economy and not the USA.

His general point is that the market is better served by independent contractors than by employees in some positions.  It’s a Randian workplace utopia view – that if everyone acts in their own self-interest all the time, everyone is served.  Workers are more efficient because they generally work harder since their income directly relates to their actions, AND they net more take-home pay.  Of course it’s also better for employers because they need fewer employees for whom they pay government-mandated taxes for benefits.

I recall studying about Lima, Peru’s cash economy when I was in grad school.   It existed with full knowledge and tacit support of the government because it provided enough income for the poor to survive – thus keeping them off public assistance and out of the budget.

Then I realized I didn’t need to start a revolution to do this.  It’s already underway, driven by…my kids?  Millennials strike again.

This article about Millennials (formerly called Gen Y) was right on target.  Millennials  “… see work as something that helps them live the rest of their lives rather than seeing work as life — in other words, they work to live rather than living to work. On the whole, they’d rather work at an interesting job for less money that allows them plenty of time out of the office (or working at home) rather than putting in 12-hour days for a six-figure salary.”

Yep.  That’s a Millennial for you.   Drives workplace managers crazy because of the low retention rates and the sometimes inflated self-worth and expectations.   Remember, Millennials are also known as the Trophy Generation.  (Read whole article here)

Dare I suggest that it’s the workplace that needs to change?

And certainly it has in many ways.  We have Gen X to thank for casual Fridays after all.   Silicon Valley is littered with modern workplaces with everything from required sabbaticals to free gourmet food to onsite spas in an effort to make getting the job done more balanced and less stressful.  It’s progress, even if it’s mostly in California.

As for the rest of us?  Well, right now the option is to choose.    Two – five weeks vacation a year in exchange for income and benefits.  It’s a classic exchange, freedom for security.

Or, the slightly terrifying Go-Your-Own-Way Gig Economy.    (It helps if you picture your boss humming Fleetwood Mac)

I’d be severely remiss not to give credit and acknowledgement to my mom, who has worked as a freelance illustrator, artist, pet-sitter, portrait teacher, and walk-leader for over thirty years.  I don’t think she ever considered herself a bleeding edge pioneer of freedom from the workplace.

Not sure where to start?  Go find a Millennial and buy them a cup of coffee.  Oh wait….that’s a latte.  Pick his or her brain about work, play, and having it all.

You might be surprised what a Boomer can learn from youngsters these days.



Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

The JOB Front

Enough talk about health insurance for a bit, okay?   I am dubbing it the Opportunity Cost of Time Freedom.

Let’s talk income.

Income needs vary.  Ability to move around for jobs vary.  Experience varies.  So, there may or may not be something here that is the piéce de résistance for you.   But something you see here might give you that spark of an idea that blossoms into just the right way for you to structure your semi-retirement.    Or, one link leads to another and so on, and down the path you can go looking for what does work for you if these do not.

Several of these links are for seasonal jobs, and many are summer tourism positions.  In the USA,  Colorado, Utah, and some California, Wyoming, Vermont, and New Mexico offer two tourist seasons with a shoulder in between to take some time off.   Also, don’t rule out the southern hemisphere for opposing seasons or Europe or Asia for Winter seasonal tourism industry jobs.

If you are interested in building a freelance business that is portable, there are a couple good starting places here.   Also links to house sitting opportunities, if blending travel with portable work is something that appeals to you.

Retail season is coming, for those of you who would like a brick and mortar job during the Fall selling season.   The job boards are good for this, but don’t forget to go to specific retailers that you would be interested in working for and fill out an application.  You can do this online, or just go to the store do it.   If you’d like something indoor/outdoor, don’t forget about the Post Office, and private shippers like UPS and FedEx.

And now is the time to begin stalking the IRS for postings for their seasonal data entry positions.  These jobs seem to post between mid-August and October 1st and run from January or February through May doing income tax related work at 23 regional processing centers around the country.  You don’t need to be an accountant – many positions are simple data entry or paperwork processing.

Go play and check these out!




Resources for Info and Job Postings about teaching English abroad

Two articles with some excellent additional links

This should help get you started and inspire some ideas!




Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

Risk Management Part Deux

*I apologize that this post is late – got a chance to do some contract work yesterday and had to jump on it!*

Last week on Wednesday, I gave you a run down on my thoughts about buying health insurance.  In particular, I gave you an analysis of looking at a high deductible policy versus my old “Cadillac” one and talked about the pros and cons of the different options out there.

This week I want to make it a bit more personal, and share some of the “aha’s” and “gotcha’s” that have come out of that decision.

Most importantly, what I want to share is that going to a high-deductible policy that did NOT have a co-pay program for doctor visits changed our healthcare behavior.

We stopped going to the doctor when we really needed to.

Why?  Plain and simple, we would have to pay out of pocket as nothing was covered until the deductible was met.

About two months ago, I couldn’t ignore an odd looking spot on my leg any longer.  I finally sucked up and made an appointment.  The doctor agreed it needed to be biopsied, which we did on the spot.  Within days I had the news that it was nothing worrisome.

Thank goodness, because the bill almost gave me a heart attack!

$148 for the office visit, and a whopping $371 for the pathologists.  And this WITH insurance adjusted rates.  This one visit wiped out half of my HSA (Health Savings Account).

Today, I got the bill for what it will cost to COBRA that policy.  It’s ridiculously expensive and not even market competitive.  After some searching and researching, I quickly identified that we could either get substantially better coverage for that amount, or just somewhat better coverage for less.  I’m going to spend more than I had hoped, but will have LESS risk.

Having had the above experience though, I will share that I do plan on springing for a policy that gives us basic doctor visits for a copay without having to satisfy the deductible.   I noticed how much we avoided seeking basic care because of the cost just over the past six months. I still have a teen at home – if he needs to see a doctor, I don’t want to second guess the situation.

Perhaps MY experience will help you get a feeling for the risk you can tolerate.

A votre santé.



Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

Becoming Your Life Risk Manager

I alluded to this is last week’s Health and Wealth Wednesday post, so I will go more into detail today.    If you are going to work and provide your own health insurance, you’re going to need to become a bit of a personal risk manager.

**Disclaimer – I am not a licensed financial planner, accountant, or insurance sales person.  I’m just sharing my understanding of what I’ve learned.**

What is “Risk Management?”

Insurance, plain and simple.    The mathematical, and statistical process of determining what the risk is of a particular event happening or not happening.  You buy insurance betting something WILL happen, the insurer bets it won’t.   It’s the gambler against the house.    How much risk you are willing to take, or will be allowed to take, drives rates when the market is allowed to function privately.

Want life insurance and you sky dive?  That increases your risk of dying, and the insurance goes up.  (IF anyone will even write you a policy.)  You can find different prices at different carriers, but certain carriers might have a more stable financial history and record of paying claims, thus charge higher rates.

Risk Management and Health Insurance

And health insurance USED to be somewhat like this.  Private market driven, rates were determined by all the variables that might increase the likelihood of the patient making a claim.  Smoking, overweight, age, child-bearing years, and the dreaded exclusions for pre-existing conditions could all get you stratospheric rates or denied coverage altogether.

Another unspoken factor in the health-insurance mix is malpractice insurance for physicians.   While not necessarily related to the cost of individual insurance, this does come into play with the COST of receiving care, as doctors order test after test, prescribe meds, and even do precautionary surgery in order to be able to defend themselves in a potential lawsuit.   The blessing of employer-provided insurance comes into play here.  With it, we have become very divorced from the true cost of delivering healthcare AND the cost of buying insurance for it.

So, previously, we had a market driven insurance medical insurance process that relied on statistics, patterns, and probabilities to determine risk which drove rate.   This left many people unable to access the market for various reasons, mostly because insurers could exclude coverage, or charge high rates when  high risk was present.   We also had an extremely high level of healthcare consumption driven in part by malpractice fears.

In VERY simple terms, what Obamacare did was to federalize the requirements of what insurers MUST offer.    No more exclusions for pre-existing conditions, but also everyone carries coverage for everything.   The concept was to spread the wealth, or in this case the lack, across everyone.   EVERYONE pays in, and those who need little care make few claims, those who need more care get service.

This means that the insurance companies can’t utilize many of the tools they used in the past to drive individual rates. We are still calling it “insurance” but it’s really a hybrid of something else now.  For example, I am 55 years old, and had my tubes tied at 40.  Obamacare still requires that my policy cover childbirth.

All services are covered for everyone.  The theory is that the pool is thus large enough to cover the higher consumers of healthcare.  What varies to the individual buyer is how much of it you pay out of pocket.

Re-Evaluating Your Insurance

Through a quirk of my company’s structure, I got a taste of this in February when I changed positions.      In my old job, I had what Obamacare calls a “cadillac” policy.  Zero deductible, $20 – $40 copays,  $15 for most prescriptions.

The most recent monthly cost on this policy for a family of four was $372/month to me.   The company had us pay 25%, so the real policy cost to the company would be 4x what I paid, or about $1488 per month.

The new position did not have as rich a policy.  The closest one would cost us $476/month AND had a $1000 per person/$2500 family deductible with a $5000 out of pocket maximum we would pay per year for claims.      I looked at the numbers and wondered….what is my WORST case scenario here?   How much money would I spend if we had a major claim?    SO,  I added it all up.

Cost of the policy to me per year                      $5,712  ($476×12)

Deductible   Max                                                             2,500

CoPay Max up to the $5K out of pocket           2,500

Potential Expenditure in one year                  $10,712

**this premium is about 35% of the policy cost, so buying this on the open market or via COBRA would be approximately $16,320 premium only.  Add the deductible and out of pocket max for a potential expenditure of $21, 320 buying this policy myself.

Now compare this to the WORST policy – the one with a high deductible, but a much lower premium.  My share is 35% of the total cost.

Cost of the policy to me per year                   $1,836    ($153×12)

Deductible $2500 ind/$5000 family              5,000

Copays up to $10K out of pocket max           5,000

Potential expenditure in one year                $11,836

**Cost of COBRA for this policy is uncertain, but since we were paying 35% of the premium, I am expecting it to come in around $437/month for the family.

REMARKABLY cost similar, in my opinion, to the total risk cost of the higher priced policy.    The difference between the top of the line and the bottom choice a mere $1124, IF I have a major claim.

But, my cost of purchasing the insurance to begin with?  A whopping $3879 difference that I would be spending, major claim or not.

So, I became our family’s risk manager.   I decided that we were a fairly healthy group, and I bet against the house that we would NOT have a major claim this year.  We moved to the high deductible policy.

Now, to be fair, we also started paying the premium difference into a Health Savings Account.   That way, we have some cash set aside for deductibles this year for any necessary doctor visits.

Bottom line.    Do you need to look at this more closely? How healthy are you and how risk averse are you?   Could you lower your health insurance costs by taking on more of the RISK?     One key to assessing this is attaching a risk value to your financial ability to pay your deductible in full in the event of a catastrophic healthcare need.

Here’s to a healthy year!





Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.

Healthcare and Insurance Choices for Seasonal/Contract Workers

Ah…the ELEPHANT in the room. Health Insurance.  The invisible handcuffs of the 21st century in the United States.

I am willing to be that some of you reading this article LOVE the idea of the lifestyle I am suggesting – work (possibly really HARD) for somewhere between eight and ten months a year, and take the other months OFF.    Big blocks of time off – not a week here or there.  For important things like playing with grandchildren, traveling the world, or writing the novel that’s rattling around in your head begging to be realized.

But…there’s the elephant.   You currently have employer provided health insurance, and you think you can’t possibly afford to buy it yourself.

You might be right IF you are married to the idea of having a low/no deductible policy and being able to see a doctor for anything, anywhere, anytime.

Love it or leave it – we are where we are in the U.S., and the cost of healthcare can be enormous.

Is the situation hopeless?    No it isn’t.  You do have choices.  Today I will outline some of those in an overview.


Basically, this is choosing to go without insurance, pay the tax penalty, and just pay for medical care as you go.     Reward?  Well, if you don’t have a catastrophic health care incident, you will save a lot of money.     There are some tricks of the trade here – you can utilize fixed fee private clinics for basic needs.  A typical appointment for something like a sinus infection would run about $50.  Mole removal typically costs $25- 30.    These clinics usually have a price-per-procedure sheet available. You can also negotiate rates with doctors and hospitals.  Skipping insurance altogether is what many young people are doing, and it is one of the reasons that the Affordable Care Act (ACA) is having some struggles.

Risk Level – High.

Medical Tourism

Many countries have private medical care that is available for purchase by foreigners.  Partially because these countries don’t have our tort legal system, the costs are lower because the doctors don’t have to purchase malpractice insurance.   Many of the facilities have brought in U.S. trained doctors, and also obtained JCAH certification. This is the process U.S. hospitals go through every four years to keep remain certified.   Articles abound of U.S. citizens traveling to places like Thailand, Mexico, and Dubai and having high risk procedures like coronary bypass surgery for 10 – 20% of the cost in the U.S.

Risk Level – Moderate, if you do your homework on the facility and practitioner.

Re-Evaluate Your Policy

This is what we did.  For years, we paid several hundred dollars a month for a no-deductible, no out-of-pocket, “cadillac” policy.  Offered by my employer, it was a sweet deal, as they paid 75% of the premium cost.     When I changed positions internally in January, I had to change insurance.   Doing the math I realized that we could move to a high-deductible policy and put the cost difference into a HSA (healthcare savings account) to pay costs prior to meeting it.   This type of account rolls over and doesn’t have to be used annually.   This HAS changed our healthcare behavior, however.

Risk Level –  Moderate IF you can bank the deductible and sit on it for when/if you need it.

Get Healthier

Well, the reality is that we ALL need to do this anyway.  But if you are going to decrease your insurance coverage, it can’t hurt to do everything possible to avoid needing health care.

Refined sugar, we know, is crazy bad for us.  Most of us are very addicted to it, and don’t even realize how much of it is in our food.  I’ve cut WAY back, and after about three weeks noticed that some things have a natural sweet taste that I didn’t get before.   I am not perfect, as my weekly frozen cola treat proves.   But, less is better and none is best.

Exercise more.  Every day.   I am working on that.

Sleep more.  Every day.  Working on that too.

Bottom line, opting for an independent-of-long-term employment lifestyle requires a different approach to many things.  Healthcare and health insurance are probably the biggest and most expensive of those.





Recovering MBA. Writer. Photographer. Scanner. Learning Addict. Airplane Geek. Teacher. Certification Collector. Serenity Seeker. Semi-retiree in training.