| Works for Me |

“Keep My Job or Open My Own Business?”

You’re in good company; it’s the ultimate goal for many employees


I’M not sure if this is a question for a career consultant.

It’s business-related, but I don’t have an actual business… yet. I work full time as a property manager, and while I’m valued and good at what I do, I don’t really get much fulfillment from working for someone else.

I’m pretty handy, and I’ve started using my skills for a side gig installing windows and doors. My dream is to be able to turn that into a real business. I have no clue how to do that, though, and I can’t afford to give up my salary.

Is there anything I can do to make this happen?


A question about creating a job for yourself is certainly a legitimate career question!

Basically, you want to trade in one good boss for hundreds of bosses, the dream of doing work you love on your own time with nearly unlimited earning potential. You’re in good company; it’s the ultimate goal for many employees.

Since you’re already in a related field, I’d start by addressing potential complications with your employer. I recommend planning to stay at your current job for a minimum of another year, while taking on a working partner, and letting your boss know about it from the beginning. Being up-front about your goals and commitment, besides being good practice, will remove a lot of the stress of trying to juggle two roles at once. You will run the risk of your employer not being okay with it, but at least you’ll know where you stand and what your options are.

If you can structure your side job in a way that will not detract from your current role, your employer may even become your biggest supporter. I’ve seen employers provide excellent contacts and opportunities for previous employees who go out on their own when it is done right.

Once you’re ready to focus on building this business up over the coming year, it’s time to think about the practical plan. Let’s start with the bottom line: What is your current income? What dollar amount would your business need to gross (earnings before taxes and expenses) in order for you to net (what’s actually left in your pocket) the same amount? Remember to take into account all the hidden benefits of your current job, such as insurance, bonuses, commissions, etc. to get a number that accurately reflects your real income.

Once you have that number clear, you now have a baseline income goal for what your business would need to achieve before you can consider quitting your job. Don’t be fooled into thinking that every dollar you make goes into your pocket. As a business owner, a good rough estimate is to plan to earn 50 percent of every dollar that comes in. The rest gets eaten up by business expenses.

At this point, it’s time to create a business plan. You’re done with hoping you’ll get your next client, and ready to create a plan to build up a successful business. The best way to do that is to create goals — big, hairy, audacious goals (BHAGs, as Brian Tracy calls them) that you’re motivated to work toward. What is your financial goal for the year? How many windows and doors would you need to install to reach that number? Where are you purchasing supplies from — is there a better option? Does it make sense to purchase supplies wholesale and have your own storage? Work to create a realistic plan that’s both exciting and possible — even if it seems impossible right now.

Next, it’s time to come up with a marketing strategy. The goal is simple: Tell more people about what you do, and help them decide to use your service. Right now, just a few people know about what you do, and they may not even know you’re looking to grow.

For phase one, which is just getting the word out, start as simple as possible. Since you already know your typical customer, consider that when creating your plan. When do they usually need a new window or door? To whom do they reach out for information? Where do they go to purchase supplies?

Your best contacts are likely people who do related construction work — contractors, handymen, other subcontractors. Create easily shareable savable marketing material that people you already know can pass on to your potential customers. It can be a digital business card, brochure, ad, or social media page — anything that they will be able to share with the people you want to reach.

Following these steps frames your endeavor as a simple mathematical calculation, along with some big decisions.

But once you’ve made it this far, the good news is that you have a business… and you’ll be ready to graduate from career guidance to business guidance.


Shaina Keren is a career consultant who helps people discover and create careers that fit their best talents, interests, and life goals. She also advises businesses on hiring and keeping “the right people in the right seat,” in a win-win approach to growing businesses and careers.


(Originally featured in Mishpacha, Issue 975)

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