Surviving Self-Employment: Getting It Done

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The idea of self-employment appeals to most people. Why wouldn’t it?

Choosing your own hours.

Being your own boss.

Working out of your house, out of a coffee shop, or out of a casino in Vegas (they have free WiFi) whenever the mood strikes.

It sounds great, doesn’t it?

Working for yourself really is a wonderful way to live. The freedom of self-employment really is as sweet as it sounds, and even better when you start to discover the hidden perks as your business grows and thrives.

But here’s the thing:

Freedom is a big responsibility.

the boss, a gent in a dapper outfit with a bowtie and suspendersMost people have been conditioned and prepared for the world of jobs.

Starting in grade school, you’re not responsible for deciding on your own priorities. Someone else decides how you should spend your time, what needs to be accomplished in what order, and by when your goals must be achieved.

If you go through college, it’s more of the same, except that there’s an illusion of choice.

Yes, you enroll in the classes you’ll need to complete the requirements for your degree, and you have the option of focusing very intently on one subject or diversifying to several others…but those choices are fairly limited depending on your end goal, and within those classes, you’re told what to learn and when.

All of that prepares you beautifully…

To work for someone else.

Transitioning from Employment to Self Employment

Being employed is a good way to gain industry experience, but no amount of success in someone else’s company actually prepares you completely for starting your own business.

actual photo of Kitty Lusby at workWhen you have a job, you have a defined set of responsibilities.

Those tasks may be clearly defined, or they might be vague. You might have only a few areas for which you’re responsible, or you might have a wide range of duties and people reporting to you.

Working for yourself, there’s no job description.

And that transition can be killer.

Even the most creative, intelligent, and motivated people struggle when moving from employee to entrepreneur. There’s a whole new set of skills to be learned and developed, after all.

Aside from the little details like learning to track expenses and prepare for tax season, building networking skills, and developing a brand identity, there are 3 main challenges that everybody faces when making the big transition:

  • The Paradox of Choice
  • Prioritization
  • Accountability

The Paradox of Choice

You’ve probably heard the fork in the road analogy before.

a road without a fork but it was a free stock photo and it fits well enough so whatevsImagine that you’re walking down a dusty dirt road in search of something new and exciting. You’ve wound through thick forests, crossed hot deserts, and now you’re among beautiful, grassy hills. As the road leads to the crest of a huge rise, you see that the road splits before you.

Will you go right, or left?

It’s such a common metaphor that we use the term “fork in the road” to indicate a choice…

But for entrepreneurs, it’s rarely that simple.

When you strike out on your own, it’s not at all like following an established path.

Instead, picture this:

You’re standing in the middle of a grassy field. Ahead of you, there’s a thick, dark, scary forest. To your right, there are tall mountains. Behind you, there’s a wild river and a little boat dock. The field continues to stretch out to your left, but you can’t see past the fog that rolls out from the woods.

There are no clear paths at all. You have an infinite number of options – you can move in any direction, but you can’t see very far no matter which way you turn.

How do you choose? Do you choose at all?

This is the Paradox of Choice.

A person presented with two or three options will usually have no trouble picking one.

When faced with an infinite number of choices, though, most people end up choosing to do nothing. This is often how procrastination takes hold of smart, motivated entrepreneurs.

Lots of brilliant people with million-dollar ideas never get much further than thinking about it.

We’ll talk about survival strategies to combat choice paralysis in just a few more paragraphs, but first, let’s take a closer look at the next problem that most people face when moving towards self employment.

figuring out priorities, brainstorming, mental mapping


When was the last time you thought about your priorities in life?

If you want to know a person’s priorities, you only need to look at how they’re spending their time. They might say that family is their biggest priority, but if 8 hours of every day are spent at work, 5 hours are spent in front of the television, and they only give 1 hour every night to family time, something isn’t adding up.

For a lot of people, entertainment is a priority.

Outside of their jobs, the majority of people spend most of their time consuming entertainment products like TV, movies, and video games. You’ll realize how true that is if you stop watching television and then try to have a conversation with your peers – most of them don’t have much to say outside of what happened on that popular show last night.

At work, you’re given tasks based on someone else’s priorities. Someone at the top level of that company decided the direction that the business should take, and they passed that information down the line until it got to you. It’s not up to you to decide what’s most important since someone else already made that choice.

Now you’ve got your own business.

So what’s important?

And you have to prioritize much more than just your business tasks – you must determine how your work fits in with every area of your life.

Is growing your company more important than spending time with your kids?

Or, if you’re single like I am, perhaps finding a suitable mate is more important to you than building a business empire. [I feel compelled to tell you that this isn’t the case for me. Just saying.]

This is probably the first time in your life that you’re thinking about what’s really important to you and deciding how to spend your time according to those decisions.

It’s harder than it sounds to determine what your priorities are and then live accordingly. As you go, you’ll find that many of the things you thought were important to you really aren’t…and you’ll discover that the things that most often occupy your thoughts aren’t what you expected.

Your priorities determine your actions, and if they’re out of sync with your goals, it’s a recipe to get nowhere fast.

But even if you’re confident that you know exactly what you want, you still need to conquer one more challenge before you see success.

graphic with some dude writing something down

Personal Accountability

One of the greatest things about self-employment is that you don’t have a boss.

One of the hardest things about self-employment is that you don’t have a boss.

Ask any successful entrepreneur what inspired them to start their own business, and odds are pretty good they’ll tell you that they wanted to ditch their boss. That’s not the only reason for striking out on your own, but it is a pretty common one.


Nobody likes to be micromanaged. A lot of people, myself included, don’t like to be managed at all.

However, there’s a clear advantage to having a supervisor or a coworker counting on you to live up to your promises.

If you agree to complete something for another person, there are immediate negative consequences for failing to follow through. Even if you don’t have any serious risk of retaliation, you’ll still experience feelings of guilt, and you’ll likely harm your reputation and damage the trust in that relationship.

It’s much easier to break promises to yourself, though.

Think about this:

funnel cake at the pahrump balloon festival 2016Why do most people fail to stick to their healthy choices, even when they have so much to gain from losing weight and getting into better shape?

Perhaps we feel a little guilty when we don’t follow through on the positive decisions we made while we were in a productive mood, but it’s much easier to rationalize and justify our failures to ourselves. Sometimes, we don’t even remember that we wanted to make a change at all!

Succeeding in your own business means learning to follow through and complete tasks, even when it’s inconvenient, when we’re not in the mood, or when it’s downright difficult to just get it done.

To do that, and to overcome all three of the major pitfalls that ensnare most new entrepreneurs, you’re going to need some survival strategies:

Self-Employment Survival Strategies

Words like discipline and goal-setting are mentioned frequently in business and self-help circles, and while developing discipline and setting goals is a good thing, that’s way too generic of an answer to actually help anyone.

Telling a new entrepreneur to be more disciplined to solve their procrastination issues is like telling your recently dumped friend to “get over it” as a solution to their emotional pain.

It’s not wrong…

It’s just not particularly helpful, either.

Fortunately, there are specific steps you can take to get through the rough patches and stay on track to succeed in your new business venture.

Don’t quit you job too soon.

jobs and work and suits and stuffIt might not be possible with every business, but even if you’re planning on opening a physical store, do as much of the prep work as you can while you’re still employed.

Sometimes there might be a conflict of interest, or your job might make too many demands on your time. In cases like that, it’s smart to find a different job rather than quitting completely to focus on your business.

Yes, it’s a lot of work, but if you can run your business during the off-hours while still keeping your “day” job, that’s the best way to get started.

Here’s why:

  • It takes longer than you think it will to begin making a steady income from your own business. Keeping your job is a way to earn enough income to relieve some of the pressure to make a profit quickly. With a steady income, you can focus on building your business on a solid foundation.
  • Your job probably puts you in contact with other people, and you can use them to test your ideas. Plus, if you talk a big game about how you’re going to blow this joint and go into business for yourself, there’s a lot more pressure to actually do it so that you don’t look stupid in front of your coworkers.
  • Even if your venture starts out great, unexpected hiccups can wipe out your income overnight – just check out my horror story if you don’t believe me – and having some banked income from your job gives you an opportunity to recover much more easily.
  • If you hate your job, keep it until your business is so successful you can’t afford to waste time at work. It will help motivate you to grow your self-employment income.

As a general rule, if you’re able to keep your job and grow your business at the same time, you should keep your job until you’re regularly making enough money from your business to support your lifestyle. When your self-employment income is covering all of your expenses, start putting your job paychecks into a bank account and live off of your business income. Once you’ve gone a full year without touching a single paycheck, it’s safe to quit – plus, you’ve got a year of income banked in case of disaster.

Start a personal development routine.

self development is important. read good books

There’s a bit of a social stigma surrounding people who read self-help books and listen to personal growth programs in the car.

Get over it.

The entrepreneur mindset is drastically different from what you’re used to as an employee. You need to get around other successfully self-employed people, and since you probably don’t know how to do that yet, a strong personal development program is a good start.

Read books like How to Win Friends and Influence People (Dale Carnegie) and The 21 Irrefutable Laws of Leadership (John Maxwell) to start building your people skills, and start shopping for seminars and good networking events where you can meet people in your field and learn from them.

The most successful people read every day, usually just before bed, and you should, too.

It might not seem important right now, but if you want your business to grow, you need to grow. It’s not negotiable. Small-minded people don’t run hugely successful companies.

Give yourself regular priority audits.

Before you do one of these audits, you need to determine your priorities.

open blank notebook on a black backgroundWrite down the areas of your life that are most important to you. Perhaps you have a serious case of wanderlust and traveling is important to your mental well-being, or maybe it’s important that you spend quality time with your family. There are no right or wrong answers, but be honest with yourself and write down everything that you need to be happy.

Once you’ve got your ideas written down, determine the hierarchy of importance. Is being well-respected more important than finding a date? Would you rather focus on donating large sums of money to charity, or getting into ideal physical shape? Whatever is on your list should be organized from the most important thing to the least important thing, whether there are 3 items or 15.

Post that list somewhere prominent – your bathroom mirror, your fridge, your closet door, wherever you’ll see it every day.

Those are your priorities.

Now you’re ready to start your audits.

Every month on a specific day, whether it’s the 15th or the first Monday of every month or whatever else you choose, give yourself a priority audit. Take a look at your schedule for the last month and determine how you’ve been spending your time. If you’ve been honest in building your priority list and the first thing really is the most important, then the largest portion of your time over the last 30 days has been spent in that area.

If your time and your stated priorities aren’t in alignment, which is probably going to be the case while you’re still adjusting to the world of self-employment, you have two choices.

You can adjust how you’re spending your time.

Or you can revise your list of priorities.

You’re the only one that’s qualified to make that decision, so do what you think is right. After a few months of regular priority audits, it will get easier to manage your goals and use your time accordingly.

Use a daily to-do list.

to do list is a vital part of an entrepreneur's dayEach morning, start your day by writing down everything you plan to accomplish by the time you go to bed. Don’t just type it on a computer, and don’t recycle the same list – actually write, by hand, your goals for the day.

There’s magic in a to-do list.

The act of actually writing down goals makes them seem more real, and it’s much easier to stay on track and manage your daily priorities if you’ve taken the few seconds to write out a plan.

Of course, things are going to come up. Your internet coverage will go out, your mom will call and want to tell you all the family gossip, and your best friend will invite you over to meet the new puppy…but even if plans change, go back to the to-do list. If you need to change your schedule, change the list, too.

Updating your list when things go askew will help keep you from spinning out of control and forgetting all of your priorities when one thing changes.

It’s exceedingly simple, but who said success had to be complicated?

planning, goal-setting, and breaking down goals into manageable and actionable chunks

Write down your short-term and long-term goals, then break them down.

Just like the to-do list, writing down your goals makes them more real.

Figure out your short-term goals, the things that you want to accomplish within the next 6 months to 1 year, and write them down with deadlines. Do the same for your longer-term goals, things that you expect to accomplish 5, 10, even 100 years from now.

Are those goals in line with your priorities? If they’re not, one or the other needs to be revised. Your goals should align with the things that are important to you.

And remember – it’s not a goal without a deadline. It’s just a daydream if you haven’t put a date on it.

Post your goals right next to your priorities, somewhere that you’ll see them every day.

Instead of a monthly audit, though, you’re going to use your written goals to help you determine your daily to-do list.

A big goal is a wonderful thing, but after you’ve determined what you’re working towards and written it down, you have to make it actionable. You’re not going to be the best-known name in your field tomorrow, but you can take a step towards achieving that goal tomorrow.

Take some time to break down each big goal into individual steps. For example, if you want to write an e-book, your steps might look something like this:

Write an e-book about self employment and publish it before June 30, 2016.

Step 1: Complete an outline by January 15, 2016 and set aside $50 per week to cover publication expenses

Step 2: Write 1 chapter per week from January 15, 2016 through April 15, 2016

Step 3: Complete preliminary revisions by April 20, 2016 and send to professional editor

Step 4: Complete final revisions by June 5, 2016

Step 5: Self-publish completed e-book by June 30, 2016

This is a bit of a simplification for the sake of this blog post. An actual publication process involves a few more steps than this, but you should have the general idea.

writing down an actionable plan is a vital step towards successAfter your goal is broken down into smaller steps (with their own deadlines) you’ll be much better able to tackle the big project, and it’s much easier to add items to your daily to-do list.

As you write your daily list, ask yourself “What can I do today that will get me closer to achieving this goal?”

In the example above, the daily to-do list might say something like “Write a minimum of 1 page,” or “Proofread and revise chapter 6.” You might not be able to publish an e-book today, but you can write a page, can’t you?

Find an accountability partner.

Having someone else to hold you accountable can do wonders for your motivation.

They’re not your boss, and they don’t have to be your business partner. In fact, they don’t have to know much about your industry at all!

A good accountability partner…

  • is someone you respect.
  • is a mature, responsible person.
  • is someone you talk to regularly.
  • will remember to check in when your deadlines are getting close.
  • wants to see you succeed.

working together with other people can be difficultIf you don’t respect this person, you won’t feel as bad if you let them down. They need to be the sort of person who cares about your success and isn’t afraid to check in when your deadline is getting close. In many cases, this person is another business owner or aspiring entrepreneur, or they’re a mentor or good friend.

Whoever you choose, make sure they’re brave enough to be honest with you, and that they’re organized enough to remind you of your commitments.

Have you ever had a gym buddy that never showed up to the gym with you?

Don’t pick that person as your accountability partner.

You might decide to have 2 or 3 people filling this role, and if you’re serious about being self-employed, you might also consider partnering with another budding entrepreneur to hold each other accountable to your individual goals.

Don’t worry. You’ve got this.

After all that, you might feel a little intimidated by the idea of going into business for yourself.

That’s okay.

You should be a little scared, but you shouldn’t let it stop you.

Think of all the people who wish they could live the entrepreneur life, but are too scared to even get started. You’re not like them, are you?

A few smart strategies, plus a heaping dose of personal honesty, and you’re well on your way to becoming successfully self-employed.

Trust me. If I can do it, so can you.

1 comments on “Surviving Self-Employment: Getting It Done”

    • Gill Caruana
    • January 30, 2018

    Thank you!! I really needed to stumble upon this right now. Advice I will heed.

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