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.

Avoid Benefit Shock

In a nutshell, I have become an advocate for independence from the traditional U.S. work model.  By that, I mean the model where you exchange sometimes extraordinary amounts of time per week, and typically 49 – 50 weeks a year, for income and benefits.

It’s the benefits that can be the big “gotcha” of this arrangement.

First, I do want to make clear that I fully support, recognize, and value working, and am not anti-big business in any way.  I’m really a laissez-faire capitalist at heart.   I get the structure.  And I get that it works for companies and it works for most people.

I’m just not most people anymore.  If you’re reading this, you may not be either.

As you begin planning to re-structure your life away from the traditional working one into a Semi-Retired one, here are some of the expenses and impacts you will need to consider:

  • Self-Employment Taxes
  • Other Insurance
  • Discounts and Reimbursements
  • Credit Rating
Self-Employment Taxes

Depending on how your employment is structured, you may be responsible for paying the other half of the roughly 15% of your wage that goes to Social Security, FICA, and Medicare.   In a traditional employment structure, half of that is paid by the employer and half by the employee.

Check with your employer.   If you work full-time, but for a limited time like a season, the employer is likely paying this.  Your paycheck will provide a clue – are SS/FICA/Medicare taxes being withheld?

If you are running your own business as a Freelancer or Independent Contractor, this will become your responsibility.  Be sure to check with an accountant, preferably a tax expert, to make certain you are handling this properly.

Other Insurance

We have talked about health insurance ad nauseum already.

Additional coverages for dental, vision, life, and disability insurance typically do not have the hefty price tag of health insurance.  That said, if you want these types of policies, be sure to factor in that cost.

A good estimate to use for the value of workplace benefits is approximately 25 – 35% of your wage/salary/income.  The difference will largely be in how much of your current health insurance premium value your employer pays.

To get a feel for how much you will need to earn to REPLACE your current income, take your monthly gross amount (before taxes are withheld) and multiple it by 1.25 and 1.35.  This will give you a range to work with.

That said, replacing your income entirely may not be your goal or need.   Just be aware that you will likely need more income to net the same amount without benefits.


Be sure to include in your budget things that your employer reimburses that will go away when you leave or retire.  Cell phone?  Parking? Transportation? Internet?   What about discounts you receive on any of these through your employer?

Credit Rating

Got a stellar credit rating?  Don’t be surprised to see it take a dip if you are not “employed.”   Even if you don’t miss a payment on something or go into more debt.

Wow…with those negatives, why would anyone leave traditional employment?  Well, often they don’t.  It’s a time-for-money exchange.  There’s a level of security in it that goes beyond just the take-home pay.

The flip side is a loss of time freedom.  Free time to do and see and be the what, where, and who you want.  It’s not about not working.  It’s about the time OFF.

My goal is to structure my  employment life to get substantially more of that in longer segments.

How about you?

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.

The Modern Seasonal Worker

I’ve been cogitating a post about the cost of independence for a couple days, but that feels heavy and just…Meh.

However, I have had a wonderful time lately ogling tiny houses and campers.  The funny aspect of that is that I don’t camp!  I can, though, completely see myself in a tiny house.

But, it occurs to me that these might be  perfect and affordable housing solutions for those of you who would like to do seasonal work in different places around the U.S.A.    Actually, they would work anywhere you are willing to drive/pull them, or for that matter ship them.  So you aren’t necessarily limited to the lower 48 and/or Alaska.

Some of the seasonal jobs with the National Park Service for example, will provide the camper space as part of the compensation – saving the time, energy, and expense of hunting up dorm or temporary housing.    People already do this with RVs, but those are generally more expensive to acquire, maintain, and operate.

How frugally, economically, and without much space do you think you could live?   

Today, go and play with the idea of being a turtle and carrying your home on your back.   What kind of freedom would it give you to take the kind of jobs you want to take if you did not have to worry about where to live when you got there?  Would being a modern seasonal worker, moving around to different seasonal or temporary jobs, work for you?

Here’s an itty bitty camper that doesn’t need a big truck to pull.  Think you could “live” in this for a season?

Click here to see the Happier Camper

Maybe need a little more space, but still want to pull it behind you?

Check out the Beauer Telescoping Camper Here

And then there’s my favorite idea; a tiny house.   LOTS of options here, and you do need a more powerful vehicle to move them.   Be still my heart…

Portable Tiny Houses in Cedar

Tumbleweed Brand Tiny Houses

General Info About Tiny Living

Article with the Author of a Tiny House Blog

Another Tiny House page

So, what do you think?   If you could travel with your own living quarters, would being a modern traveling  seasonal worker suit you?

Think about it!

Have a fun day-dreaming.




Make Your Own Checklist for Semi-Retirement

Last evening, my husband and I were discussing a new employee of his who was struggling a bit with the process of the work.  I suggested that my husband make an outline, or checklist, for the kid to follow.   Perhaps having it written down is how he learns?  Or perhaps he just can’t “see” it when he hears it?

This works for planning too.   In flying, it’s “Plan the flight.  Fly the plan.”    Planning gives you an opportunity to examine the situation in advance, and make the necessary adjustments BEFORE you begin.

Starting is as simple as making a list of the variables that affect you.

Try taking these items and decide which of them would be relevant to what YOU need to live a semi-retired lifestyle.  Try putting them in an order that flows for you.  What has to happen first? Second?

Create YOUR checklist for Semi-Retirement.
What is your timeline?

(Is this something you can control or change?)

Debt  Minimization Plan
Physical location

(One or multiple?  Fluid?)


(Tiny house? Portable?  Multiple?)


(Public?  Vehicle? Scooter?  Combo?)

Present Job Skills Inventory
Needed Job Skills Inventory
Physical Limitations
Healthcare and Insurance
Income Sources in Place
Education or Certification Needed
Citizenship or Immigration Issues
Taxation Implications

(Start with how much you NEED.  Focus on how much you WANT.)

Job Stacking Options

(More than one “job” at a time for periods of time)

Equipment or Supplies Needed

(Sailboat?  RV?  High-end Camera? Laptop?)

Disposition of Unwanted/Unneeded/Unnecessary Belongings
“Ideal” day in your life
“Ideal” blocks of time off or time of year off
What is your “dream” job or work?

How can you get that job? What needs to happen?

What skills or training or experience can you get now that will make that happen?

Time off plans

(What do you want to do?  Where?)

Do you need or want a fall back plan?
Money handling and banking process

(Online?  International?)

Who are your cheerleaders or where can you find them?

(The ones who will support and encourage you.  Meetups?  HR?  Forums.)

This list isn’t all-inclusive, but it’s a great starting point.  Examine each point and see if it is a topic you will need to address.  If not, cross it off and move to the next one.  Start thinking (daydream!) about how you want your life to look.

How many things are on your checklist?  Are you closer than you thought you were to being able to make this happen?  Farther?

What do you need to do FIRST?  What CAN you do now?

Plan your semi-retired life.  LIVE your semi-retired plan.

Oh yeah.  MOST IMPORTANTLY….make it FUN.



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!

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.



Hope for the Animas

The picture that you see in your email with this blog is the Animas River in Durango, CO.  This is the river that received the dump of toxic metals and waste recently when EPA sub-contractors broke a dam in an abandoned mine.

Durango is just about my favorite place to be in the USA.  I love that town, and would travel there all the time if I could.  My heart was just broken by this news.   However, there are reports that the river is coming back and the toxicity may not be as bad as initially feared.

So today, I’d just like to share some of the Animas and Durango with you.  If you haven’t been there, put it on your list!

downsized_0523120804 IMG_0971 IMG_0976 IMG_0987 Durango Moon

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!




Embracing the Dance

There’s a popular meme on Facebook these days that says something like “Taking one step forward and one step backwards isn’t failure, it’s a cha-cha.”

Some days, I wouldn’t mind smacking the people who come up with these adorable little Pollyannaisms.

Moving forward on the new life/work relationship I am working to construct, I find that the most constant mental challenge I am facing is holding the line.    When I get a setback in my plan, such as something (COBRA) coming in WAY more expensive than it should have, or I don’t get work days that I hoped to get, or I have to PAY to register to be a substitute teacher, I find my mind races right toward the familiar security of finding a JOB.

Not the kind of jobs I WANT to do – contract, seasonal, temporary, freelance.  The kind that sucks up all my time in exchange for some amount of money that is “enough.”

My brain wants what it knows – the “security” of a steady reliable income and the blasted benefit of health insurance.   This feels safer somehow, even though intellectually I know it’s the absolute opposite of my heart’s desire.   I recall reading a statistic, no doubt manipulated, that surveyed Americans frequently report a willingness to give up freedoms in exchange for security.

I hate that.  Hate it about myself when I fall prey to it.   The anxiety and fear of the unknown.  I have to consciously fight the temptation to apply for positions that would only lock me right back into the handcuffs I so diligently Houdini’d out of just weeks ago.

The idea of applying for immediate openings teaching secondary school is definitely tied to the anxiety I feel about this massive life change I’ve made.  I DO want to look into this more, and I do believe teaching may ultimately be a very good place for me.  But, I do not want to rush it.  And I was doing just that.

So, this morning, I am taking a deep breath, and reminding myself not to give in too easily.  Hold the line.  Don’t bolt at the first setback (or second, or third) and head for any port.   Set the sails and weather the storm.  It might just be a small squall that will collapse under its own weight.

And so, this week, a cha-cha.   Got an extra day of work I wasn’t expecting at the summer position.  Yay!  A victory.    Got the COBRA pricing.  Aye.  Two steps back.

Queue the music.

Have a spectacular day.






Over Fifty And Two or Three Weeks Vacation Isn't Cutting It Anymore? What If You Could Get Two or Three MONTHS Off Every Year?