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.