How To Become Self Employed – It’s Totally Possible!

Self Employment Is Fun

If you’ve landed here, you’re searching for a new and exciting journey – Welcome! I hope you find some information here helpful in your quest to become self employed.  I am also in this journey and am happy to share what I’ve learned.

Why Self Employment?

Before getting to the “how” of being self employed, it’s important to ask WHY you want to be self employed to begin with.  The reason you’re wanting to be self employed may be different for all of us but it’s important to look at before starting out on your own.

There is safety and security in a job – a wage/salary and oftentimes health benefits, life insurance, and a 401k or other investment options.  With discipline, you can save some money and work toward retirement.  Also, you don’t have to worry about a lot of the headaches your boss has now.

And if you are currently in a job you don’t like, couldn’t you just look for another one?  Or maybe jump into another career altogether? Knowing the answer to these questions is important before starting out on your own.

Being self employed also carries with it a lot of additional expenses that you have to pay out of pocket – taxes (which are HIGH in self employment) and health insurance (can easily run well over $1000/mo.).

These are all things to consider before jumping headfirst into your own business venture.

Self Employment Goals
Photo by Laurie Anne Robert,

But if you’ve given this some thought and are still wanting to pursue that dream, I applaud you and wish you all the best!

Being self employed can be a lot of fun.  Below are a few of the more common reasons people decide to take a plunge into the exciting but unpredictable world of self employment:

  • More flexibility
  • Make more money
  • More independence and control
  • Don’t like your current career or job
  • Don’t like your Boss (it’s ok to admit this:)
  • Want to make a living doing something you LOVE

I wanted to get started for ALL the above reasons (although my boss actually treats me pretty well).

But beyond that, you have to know what you REALLY want to do?  What is it that’s led you to search for self employment options?  I had to answer these questions myself and, while I don’t have all the answers yet, I definitely have more clarity.

What helped me discover my true employment passion is finding a way to narrow down all of my interests.  I love doing a lot of things but could not figure out what I was truly PASSIONATE about so I couldn’t narrow down my career options – a good problem to have, but also frustrating!  I recently read an article by Steve Pavlina about finding out what really makes you tick – it can be found here.

In it, he gives a simple, yet practical method of narrowing down what you’re passionate about (purpose of life stuff), and it really helped me to find my way.  I knew I wanted to work independently but I truly had no clue as to what it was I REALLY wanted to do!

Steve’s tool really clicked for me and provided the clarity I needed in my career search.  I hope it helps you as well.

Self Employment How To

Who Is Cut Out For Self Employment?

I think the long and short of this is ANYONE can be self employed – but there are a few characteristics of the successfully self employed that should be noted here:

SELF MOTIVATED – Regardless of what you pursue, it takes a lot of stamina to be self-employed. Working when you don’t feel like it or tired is just part of the routine when self employed. Those successfully working as self employed generally work long hours and realize things don’t happen overnight.

DISCIPLINED – Getting started is easy.  You have all the energy and excitement to get some momentum going.  But after a few weeks, months, or years – maintaining that motivation can be difficult!  Finding the ability to keep moving day after day is huge if you want to make it!  It helps to have long and short term goals in mind to keep you going when things get tough. More about setting goals can be found here

FLEXIBLE – Being able to roll with the punches is critical.  There is always something that comes up which can derail everything that’s been set in motion.

For example – In my own little business, I have a very limited amount of time to work.  I currently have a full time job and a big family (7 of us!) so I always set up a plan each week as to when I can carve out some time to work on my business.

How To Make Time For Your Business
Make Time For Starting Your New Business

Most of the time I set it up for a couple hours before I have to go to work during the week.  I look forward to this time!  However, my job requires a lot of unanticipated travel which often leaves me staying up well into the night so my nice plan of getting up early to build my business is OUT.

I refuse to give up!  I find a way to work in the time the following morning or in the evening after the family has gone to bed.

There will always be something in the way and I’m sure you could come up with a few dozen examples of your own of how things simply don’t go as planned!

It’s ok – just roll with it and readjust!  It’s what successful people do when they come across setbacks and you’re no different than they are.

Keep your head up – the worst thing we can do is develop a negative attitude and stop working toward our goals.  That’s a recipe for becoming bitter down the line – not helpful.  Shake it off and move on.  Always keep in mind why you wanted to be self employed to begin with and don’t quit!

I offer more tips and information on this here!


DO A PERSONAL EVALUATION – In order to make it for the long haul, you need to enjoy what you’re doing.  It may sound simple but can be harder than you think if you are interested in a lot of careers.  Maybe you’re lucky and already know what you want and that’s great!  But if you’re like me and have a hard time narrowing down your options, do a self inventory which will give you more clarity!  An great example of how to do this can be found in Steve’s article here.

SAVE MONEY BEFORE STARTING – No matter what employment endeavor you’re planning to pursue, it’s a great idea to beef up your savings account.  As you go through the planning process you’ll see there are a lot of expenses that can add up (both anticipated and unanticipated) so set as much aside as you can!

DECIDE IF YOUR QUITTING YOUR JOB RIGHT AWAY OR DOWN THE ROAD – Depending on your chosen career path, you have to determine if it’s financially feasible to quit your day job altogether and just go for it.  This could be scary unless you know you’ll be making money straight out of the gate.

Or maybe you are in a position where you simply need to keep your job for financial stability and benefits and just pick away at developing your side hustle.  That’s the case for me –  I have a large family and need to pick away at the business a few hours here and there each week.

Self Employment Goals
Photo at

Because of this I’m learning patience.  I have to work a lot of early morning hours or stay up late to get some work done.  In fact, as I write this it’s 6AM on a Monday.  In 2 hours I’m off to work at my job for the rest of the day.

Although I get tired sometimes, I have peace of mind knowing my business is slowly growing and I still have the security of a paycheck and benefits from my job.  This will carry me and the family through until the business makes enough money to support us.

I love doing my side gig but know I simply can’t put my family at financial risk by quitting my day job…at least for now.  They come first.

Whatever you’re situation – if you’re hungry enough to make your business happen, you’ll find a way to put in the time, whether it’s part time or full time.


Again, this will depend on the type of business you have.  If you are selling a product, you may need additional storage space and/or shop to work in.  If you are a Consultant business, you could rent or buy an office space or simply work from a home office.

Work From Home Options
Self Employment In Retirement

Ideally, it’s great to work from home at first if you can.  If anything it’s helpful to “get your feet wet” before jumping in head first into your new business.  Renting an office or storefront can be expensive.

Not only that – if you start your business and decide it’s just not what you expected you can bail out much easier and with less at stake if you didn’t spend a bundle of money on a rental space.

Having said that – there are some businesses where you simply can’t get around this.  For example, if you are buying a franchise like a “Dollar Tree” store or something similar, you’ll need a large store space.


Finding the time to devote to your new self employment endeavor is very tough.  Be specific when figuring out the time you’ll need to devote to this.  You’ll have to add all the time your spending throughout a day like a full time job, family commitments, social events, church or school activities and the list goes on.

Look at your schedule and pencil in time devoted to your new business.  For me, that time is set aside for 2 hours before I go to work 4 days a week.  And on occasion I can leave early from work so I can put a few extra hours in then as well.

Because of the type of business I have (blogging), I either work from home or at a coffee shop near my job site.

Self Employment Options

This may be different for all of you.  For me, I didn’t want to lose family time so I picked times to work when it wouldn’t interfere with family stuff.

The important thing here is to work it out with your family and friends.  Letting them know you’re starting a business is important – and reassure them you will still have time for them and stick to that.

Keeping that balance is super important – it’s not worth losing your family just to be self employed!  When I first started my business, I wanted to work on it all the time.  However, I’m old enough now to know what’s important.  If things crumbled apart at home, I’d be pretty angry at myself for putting my business first.


If you’ve decided on what your business is going to be, it’s time to put a plan together.  What your plan looks like and how it’s structured will depend on what type of business you have.

Self Employment Business Plan

Sole Proprietorship – Great for starting out.  Supports a low-risk approach for business owners just getting started.  You have complete control of your business and are considered a sole proprietor when doing business activities but don’t register as any other type of business.

Also – You’re personal and business assets are not kept separate from one another.  So you can be held liable (personally) for any debts of the business.  Banks can be sometimes be hesitant to lend to sole proprietorships for this reason.

You can still get a trade name, however.  As long as you keep your business small initially, it’s a sensible way to go.

Partnerships – As the name implies, it’s joining forces with another person or persons.  There are a couple of different distinctions here: LP (Limited Partnerships) and LLP (Limited Liability Partnership)

Limited Partnerships – LP is set up so with one partner having unlimited liability and the other partners having limited liability.  Since the general partner has unlimited liability, his/her profits are subject to self employment taxes.  However, those partners with just limited liability have less control over the company than the general partner.

Limited Liability Partnerships – gives limited liability to EVERY partner and will provide protection for each partner from any debts that go against the partnership.

Limited Liability Company (LLC) – Can involve one or more people.  You can gain the advantages from the Partnership and Corporation models and gain protection from personal liability.  So in case of lawsuits or bankruptcies, your valuable personal assets like home, car, bank savings etc., won’t be at risk.



Business Plan Templates – Whatever your chosen business idea, it’s smart to develop a solid plan to help guide the direction of your business.  A business template can be helpful with that – I found several good examples of business templates here.  It offers a lot of great options for new businesses and those already up and running.

Registering your business – If you are starting up a new company Not all businesses need to be registered.  For example, my little blogging business does not need to be.

For guidelines on how and when to register your business, the Small Business Administration (SBA) discusses it’s guideline here.

There are many different types of businesses out there, often falling under a category of skilled labor or professional jobs.  You’ll have to check with your local county or state offices about if you need to register, whether you’re in skilled labor like construction, plumbing, dog walker etc., or professional jobs like accountant, engineer, web developer, to name a few.

Regardless of the kind of business, it’s smart to check in with the Small Business Administration for the state you’re living in.  I called them when gathering information for my business and they were and incredible source of information and very helpful.  Best of all, it’s free!  The link to their site is here.

Save Money For Retirement For Self Employed

Don’t Forget To Set Aside Money/Investments For Retirement

This can be difficult at first since so much of your earnings goes into living expenses or back into your business. Whatever you can set aside will be helpful down the road.

The IRS has information on how to set up an individual 401k.  It can also include employees.  You can glean a lot of good firsthand information about this firsthand from other small business owners for the inside scoop on how they plan to retire.

Or you can also check in with an investment adviser.  I’m lucky – I have a friend in that line of work who helps me sort it all out.  Unfortunately I don’t have a great mind for investing so I appreciate all the advice I can get.  Thankfully, my wife is pretty darn good at it too!

Prepare To Pay Taxes

OUCH!  I know, this is a big bummer about owning your own business.  There are ways to cushion the tax blow with business write-offs etc., but there’s no getting around the fact that you’ll be paying a lot out of pocket for taxes.  The link to the IRS site for taxes on a small business, getting an EIN (Employee ID Number) is here .

It’s a bit hairy to understand, but very important in setting up your new business. You’ll have to know how much of that hard earned profit goes back to the government, a sad but true reality.

Don’t dwell too much on this, though. It may be helpful to simply talk to a tax adviser or accountant before you start your business to get an idea of just how much you’ll pay and what can be offset.

How To Be Self Employed

A Few Self Employment Ideas

I hope you are jumping into the wonderful world of self employment with a clear passion or interest in mind.  However, if you’re like me, I was all excited to research how to be self employed but had no clear direction at first.

I am interested in a lot of things and couldn’t narrow it down!  Plumbing, Construction, Blogging, Carpentry, Farming – these and many other ideas came out on top. After doing the exercise by Steve Pavlina here, I had a much better understanding of the direction I wanted to go.

How To Be Self Employed

What I also found helpful is writing a super long list of self employment options. Below is the list I came up with.  I basically “free associated” this list, not that I had a particular interest in any one of them.

It was helpful just thinking of absolutely ANYTHING that came to mind – it really got the creative juices flowing.

Once done with the list, try to find your “top 10” or “top 5” ideas and do an extensive google search on each of these.  I hope that by the time you’re done, you’ll have the “aha” moment you’re looking for!  Ok, here goes…the list in no particular order…


Carpenter, Plumber, Blogger, Realtor, Insurance Agent, Affiliate Marketing, Construction, Franchise owner (Dollar Tree came to mind), Trucker, Uber or Lyft driver, Grocery Delivery service, Home Cleaning Business, Carpet Layer, Ebay business selling birdhouses, Amazon Associate, House Painter, Gopher and Mole Trapper, Building and Selling Chicken Coops, Selling Firewood, Welder, Electrician, Farmer, Freelance “Do It Yourself” house/yard projects, Flipping Houses, Deck Builder, Private Counseling Business, Opening a Coffee Kiosk or shop/bookstore.

I talk more about great online business ideas here.

I’ll stop there with my list – it’s a rather random collection of ideas.  But they all appealed to me on some level.  After doing my researching and assessing my finances, I ultimately decided on helping others through Blogging/Affiliate Marketing.  It appealed to me and gives me a chance to write about my other interests as well!

Becoming Self Employed
Photo By Annie Spratt

Ok – here are a few other ideas not on my list but hopefully helpful in stirring the pot of career ideas for you!  Here goes…in no particular order:

Tatoo artist, Tatoo Removal shop (don’t laugh – there’s a market there:) Mechanic,  Restaurant Owner, Web Developer, Web Designer, Architect, Engineer, Small Appliance Repair, Carpentry Shop, Private Tutor/Teacher – online or in person, Personal Coach, Opening a Shoe store, Small Engine Repair, Freelance Writer, Online Expert, Flower Shop, Sewing Shop/Seamstress, Computer Programmer, Telemarketing, Roofing business, Installing/Repairing Gutters, Dog Walker, House Sitter, Dog/Cat Boarding, Baby Sitter, Daycare Provider, Foster Home, Medical Transcription from home, Business Consultant, Home Organizer (you can start with our home), Tractor work (leveling driveways, using Brush Hog etc.), Furniture Builder, Computer/phone Repair, House Painter, Party Planner, Accountant from your home, Tax Adviser, Lawyer (home based office), Private Therapist, Junk Hauler, Tree Stump Removal, Fishing Guide (wish I was a better fisherman:), Local Tour Guide, Meal Planner, Nursery Business (plants or kids), Graphic Designer, Chimney Sweep, Bed and Breakfast, Used Clothing store, Used Tools store, Used Building Materials Store, Butcher Shop, Green Grocery store, Drop Shipper, Mason, Concrete/Pavement/Driveway Repair, Teaching People How to Use Their Computers in their own homes, Driver Instructor, Bee Keeper, Fitness Instructor, Running Coach, Chef, Baker.

This list seems long but the number of self employment avenues is nearly limitless!  Just get creative in finding out what works for you.  In fact, think about combining 2 or more of the above options to make a great FULL TIME income!  

My number one recommended business choice is discussed here.

Talk To Others Who Are Already Working In Your Career Choice

Regardless of your chosen career path, it can really help to pick the brain of someone who is already successfully doing it!  You can gather a TON of useful information about the business – like finding out what they love about it, the struggles they’ve had, and the pros/cons of the business.  This may dispel any myths or misconceptions you had and help you make an informed choice on whether this career is a good fit for you or not.

For me, it helped tremendously early on in my search for legitimate self employment options. I thought that being an insurance agent was the ultimate career switch for me – it offered a lot of independence, rewarded hard work, and can be a lucrative career over the long haul.

Self Employment Options

I spoke to a friend of mine who is already successfully doing this and he informed me just how hard it can be to get off the ground financially.  Finding and converting leads can be tough and you’re almost 100% commission based.

So after hearing him out, I decided against it and I don’t regret it.  It may have worked out over the long term, but would have really pinched our family financially early on, posing too big of a risk.

It just helps to interview someone, or many business owners, as part of your career research.

See a review of the business model I’m using here.

Final Thoughts

So it may seem like a lot of preparation and planning to get your business up and running, but oh so worth it!  Truth be told – there are many parts of a small business I don’t enjoy doing – like trying to learn about small business taxes or figuring out what business structure to use etc.

But I never lose sight of my goal for independence and freedom from the daily grind and it keeps me motivated each day.  And now that I’ve found what I LOVE to do, I can’t imagine turning back now.  I hope you’ll stick with it too.  I also hope you’ve gained some valuable insights here in your quest for self employment – best of luck!!

Self Employed Ideas