The Pros and Cons of Your (Yes, "Your", I Read Your Mind) Future Dream Jobs

Do you scoff at instructions, digging into projects without restricting guidelines? Are you a goal-setting visionary? Do you see interesting start-ups or projects and think, "I can do that!"? If so, you're cursed with my busy entrepreneur brain. I'm always dreaming up beautiful businesses, whether I want to or not.

Every time I see a retail space for rent in downtown St. Augustine, my favorite place in the world, I vividly dream of buying it and opening a business. Damn you, entrepreneur brain. 

After years of coaching people, getting coached, and interviewing others I've come up with five indie business jobs creative entrepreneurs want to get start and today I'm sharing the pros and cons. I'd love it if anyone with experience in these fields with chime in with their experiences in the comments. Let's start with The Universal Pros and Cons of being a Small Business Owner:

Pros: you answer to no one/you're the boss and make the rules, freedom and independence, make your own schedule, pride/accomplishment of business ownership, often creatively fulfilling/rewarding

Cons: start-up costs, you work more hours, you work harder and longer, your pay isn't usually hourly and directly dependent on the work you put in vs. hourly wage work, you have to love it and be passionate to succeed even when it's hard, blurring your hobby and work can ruin the fun of your hobby, blurring your work and home space can ruin the "relaxation" of your home space

1. Cafe or Restaurant Owner 

Pros: working with food (if you're a food lover or love to cook), more recession-proof, rewarding
Cons: managing and finding a good staff is challenging, keeping up ever-changing with rules/laws/codes/inspections, higher start-up cost, finding a good location, time sucker, big time

Tip from Michelle, owner of a successful BBQ restaurant:

"Restaurants are a lot of work. Don't get into it unless you want to work hard. It took as lot of years to get a good crew that would allow me to finally be able to work 20 to 35 hours a week. Don't open a restaurant just because you 'like to cook'. You need to know how to manage a business, then you buy or open a restaurant. You have to really want it, this business is going to be your baby."

2.  Online Reseller (Vintage or otherwise) 

Pros: low item acquisition cost, low start-up cost, fairly location independent, can work from home, can resell a low cost item at a high profit, customer service isn't face-to-face, very flexible, constantly need to acquire new merch to survive- it's stressful
Cons: requires some knowledge and/or research, listings/photography/hunting/cleaning is time consuming, storage can be expensive or take up home square footage, with online rankings pleasing cantankerous customers is paramount

The gorgeous garden next to my "dream future business". It's romantically lit by lanterns at night.

3. Rental Property Manager/Owner 

Pros: passive income- do what you love most of the time and put that rent check right into your bank account, homes/apartments/retail space purchased excellent money investment/asset
Cons: high start-up cost, upkeep expenses, dealing with tenants: damages, evictions, etc., finding tenants

Tip from Grace, owner of 7 rental properties and co-worker with me at Shakti Life Kitchen:

"You can start for $10,000 if you buy a house in a bad area. [Renting properties] is one of the best ways to get ahead in life. I hire other people to do the hard stuff like evictions and harder repairs. I love it." 

4. Writer (traditional books, eBooks, blog, journalist) 

Pros: extremely location independent, creatively satisfying, rewarding, way to inspire others/fulfilling
Cons: writer's block, very hard to get paid well (or at all) in this field, considered a "dying" industry, saturated industry

5. Retail Shop Owner (art, indie stuff, books, vintage things, etc.) 

Pros: creatively fulfilling to have your own space to arrange, a way to really feel like a part of the community and influence it, face-to-face customer interaction can be fun/rewarding/good networking, stress of having to ALWAYS need new and ample merch to survive
Cons: rent expense is often very high, hard to find a good location, very hard to keep these open now-a-days (I see them close left and right), hard to compete with big business

Bonus: Pop-Up Shop/Portable Boutique or Food Truck Owner 

Pros: No rent, highly flexible, fun creative work, meet lots of interesting people face-to-face, often working outdoors in fun environments like markets and fairs
Cons: start-up cost to outfit your truck, could be difficult to find where to set-up shop, lots of behind-the-scenes work between set-ups, setting up in different places often time-consuming and energy-sucking

What are your dream jobs?  I occupy two of the niches above and have actively tried to get into each one of the ones above..

Do you have any of the jobs above? Any experience in those common fields? Do chime with pros/cons of your own.

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