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4 Major Challenges Of Being Your Own Boss (And How To Overcome Them)


by Katie Lundin of crowdspring

Being your own boss is living “The Dream,” right?

But, like anything truly worth doing, being your own boss comes with its own set of unique challenges.

The proverbial “buck” stops with you.

There is no manager to help you when things get tough.

No kindly senior supervisor with years of experience and wisdom to guide you.

You are that manager. You are that kindly voice of wisdom and experience.

You alone are responsible for the success or failure of your business.

So if you’re an entrepreneur, or want to pursue entrepreneurship, it’s time to start thinking ahead.

How can you be your own boss?

What are the steps to becoming a business owner?

What skills do you need to be an entrepreneur?

What are the requirements to start a business?

What obstacles may get in your path?

And what will you do when you meet them?

What will you do as an entrepreneur?

If you’ve been putting off starting your own business, you’re hurting yourself. Tomorrow is an entrepreneur’s enemy.

Here are 4 of the most common challenges you’ll encounter running your own business and proven tactics to help you overcome those challenges.

Challenge #1: Maintaining Motivation and Dedication.

Being your own boss opens up a world of almost unlimited possibilities each day.

You get to design what you do and how you’ll do it.

Will you work from an office or work from home? Take meetings or work solo?

Or… maybe sit on the couch with a bag of chips and binge-watch Stranger Things for the third time.

It’s up to you how, when, and where you choose to work. And, with no one “above” you to hold you accountable, it can be tempting to slack off.

If you work from home, those temptations and distractions are likely even stronger.

The kids want to play with you, your spouse wants to plan next week’s dinner menu, and your new Nintendo Switch is calling from the entertainment center.

One of the biggest challenges of being your own boss is having the dedication and motivation to make the right choices when the going gets tough. Or when the going gets even mildly uncomfortable – which it will.

Investopedia lists “motivation” in first place on their list of “10 Characteristics of Successful Entrepreneurs” and “dedication” in slot number three.

As the driving force of your business, if you stop, well… driving… your business won’t survive.

Holding onto your passion and dedication is what will keep you motivated for the long haul.

Kelly Donovan, professional resume writer and entrepreneur, shares:

As a self-employed person, it’s easy to be motivated to complete tasks for customers since there are dollars tied to those tasks. But finishing other, non-billable, tasks requires self-motivation.

It’s up to you to find a way to motivate yourself to complete those vital, but sometimes not-so-fun tasks that keep your business moving forward.

And even if you fail, don’t despair. Successful entrepreneurs know that failure is rarely permanent.

Your Success Hacks.

Know your “why.” Keep your finger on the pulse of what motivated you to start your business in the first place. When you started your business, you were probably pretty excited about it. Why?

Take a moment – or, let’s be real, several moments – to examine your personal values. What values are most important to you? And, what about your business resonates with those values?

The overlap between your business and your values creates a lasting resource of motivation to which you can always refer back.

Write it on the wall. Take it one step further by creating a why statement that sums up that relationship between your business and your values. “I do this because…” And then post that statement somewhere you can see it and draw strength from it whenever you need it.

Successful entrepreneurs share common habits. Learn them.

Challenge #2: Using Your Time Wisely.

Your time is valuable.

In fact, it might be your most valuable possession.

This is true for all people. But, it’s particularly true if you are the leader of a company.

Your livelihood and the livelihoods of all your employees rely on you.

Your time is also a limited resource. No matter how much we wish it weren’t so, there are still only 24 hours in a day.

And as the boss, your time will also be in constant demand.

Employees will come to you with questions. Clients want to speak to the “CEO.” And other entrepreneurs will seek you out for networking purposes or just to “pick your brain”.

It can be easy to become reactive in an environment with so many endless demands for your time and attention.

But, reactivity is dangerous. Project manager and training developer Tara Duggan points out:

Reactive leadership occurs when you don’t plan ahead to handle problems or opportunities. By reacting to situations only as they arise, you may fail to avoid a crisis or exploit a chance to succeed… Reactive leadership handles only the problems occurring right now. This management strategy makes prioritizing and focusing on the long run more difficult.

If you’re going to run a proactive business and accomplish everything you need to accomplish, it’s vital that you use your time wisely.

One way to do this is to leverage others.

For example, it’s not easy to come up with a name for a new business. It took us over 50 hours to come up with the name “crowdspring”.

And even if you find a business name, you still need to build a strong brand, starting with an effective logo design. This is where professionals, like the 210,000 designers and namers on crowdspring, can help.

Among other proven strategies – declutter your life. As we wrote in 5 Scientifically Proven Ways to Improve Your Focus and Concentration:

Whether or not you are particularly attuned to the mess inhabiting your life, clutter will still have a noticeable effect on your concentration. Researchers with the Princeton University Neuroscience Institute discovered that having too much clutter decreases the brain’s capacity for focusing and processing information. Your brain becomes overly distracted by the mass amounts of clutter threatening to swallow you whole, and it renders you unable to accomplish much.

Professional organizer Amanda LeBlanc says it’s not just about clutter, it’s also about having the right tools for the job:

“If you’re always getting up to find something you need, it’s difficult to concentrate on your projects. There are many studies showing that once a person gets up from something they are working on to look for supplies, they are much less likely to return to what they were working on when they left.”

Your Success Hacks:

Prioritize, prioritize, prioritize. If you’re rushing from project to project because it feels like everything needs to get done and it all needs to get done now! …it’s time to take a step back and re-evaluate.

What tasks bring the most value to your business? And which tasks must be completed by you?

Take the time to really look at the big picture and rank tasks in order of highest to lowest priority.

Tackle the items that bring the most value to your business first. And, make sure that you do your part in any team efforts so that you keep the team moving forward.

But, delegate items that you don’t have to handle personally.

Be careful when creating to-do lists. They can hurt you and your business if done improperly. As we wrote in Why “To-Do” Lists Are Hurting Your Business:

To-do lists are often recommended as good strategies to increase productivity and efficiency. Walk through a typical office and you’ll probably notice lists, post-its, and other reminders littering desks, laptops, and smartphones – manifesting in a giant reminder of things that haven’t been done. While the idea is for these lists to serve as a reminder, they end up having a negative effect on our psyche… and in turn, our overall output.

In 1927, Russian psychologist Bluma Zeigarnik found that waiters remember orders only as they were serving them. In his culminating study on this psychological effect, he realized that this worked universally throughout memory recall:

A quasi-need persists if the task has not been completed to the subject’s own satisfaction regardless of whether this is equivalent to what may seem from another’s inspection to constitute “finished” or “unfinished”. Tasks with whose solution the subject is not content will function in his memory as “unfinished” even though the experimenter may have classified them as completed tasks, and vice versa.

Basically, Zeigarnik found that our brains will literally nag us if we know that there are more things for us to do. And just like normal nagging, this self-nagging can prove to be unhealthy, causing us to put unnecessary criticism and pressure on ourselves.

That sort of stress can seriously impact a person’s productivity, and in turn, your bottom line … Despite our reliance on the tactic, research suggests 85% of a person’s output includes tasks not included on their to-do list, and that 41% of to-do list tasks never get tackled at all.

If you don’t have a team to which you can delegate any tasks, it’s time for you to master this next hack…

Learn to say “No.”

No one likes to say no. It makes us feel icky.

We don’t want to let people down and we don’t want to let go of “what might have been” by turning away opportunities.

But, if you’re going to reclaim your time and forge a proactive, purpose-driven business, you’re going to need to get picky about how you spend your time and learn to say no.

Business coach and entrepreneur Lanna Hill recommends that you run tasks and opportunities through this simple filter:

“I have a pretty easy question… When you get an opportunity or when something’s come your way; firstly, is it income-producing? Or, is it getting you closer to your goals?”

If you can’t say “yes” to either question, that’s a hard pass.

Keep your time and your energy focused on the tasks that are truly necessary to move your business forward. And, just say no to the rest.

Challenge #3: Creating Work/Life Balance & Setting Boundaries.

Mastering work/life balance can be tricky in the best of circumstances.

When you’re riding the high of starting your own business, it’s even harder to remember to leave enough time for your personal life.

And, by the time you’re ready to reclaim some semblance of balance, it can be very tricky to do.

You’ll find there’s no shortage of work, and you’re the one who has to do it.

This can make being the boss a very lonely prospect. No one likes to be the last one working while all of the other kids have already gone out to the playground.

On the flip side of the coin, people often assume that you can walk away whenever you feel like it because you’re the boss.

You know that you can’t walk away from your responsibilities, even if you may want to. But, not everyone will get it; and that can create strain between your work and personal life.

As Charlene Jimenez of The American Genius reflects,

Because you’re in charge, your family and friends will assume that you can leave work or stop working whenever you want. They may expect you to leave at a moment’s notice to join them at a movie theater or out to lunch. Setting and enforcing those boundaries can be difficult.

If you’re not careful, you will find yourself giving either your work or your personal life short shrift while you negotiate personal and professional boundaries.

It’s up to you to create a schedule that optimizes your work productivity while still leaving ample time for life outside of your business. After all, freedom of time is a prime element of the entrepreneurial dream.

Your Success Hacks.

Make work social. Build socialization time into your workday. People need human interaction. So, if you find that you’re yearning for a break, use the time to check in with your team.

Showing interest in your employees helps to build a stronger team bond. And, it’ll help you get the socialization you need. Plus, if you enjoy the people you work with, it makes every day at work feel a little bit less like… work.

You can also seek out friends in your field. Find other entrepreneurs who can relate to your experiences, provide fresh perspectives and help you grow.

Finding ways to socialize at work in a productive manner is a fantastic way of optimizing your time while making it a little less lonely at the top.

Work with your patterns. Whether you know it yet, or not, you have a most productive time of your day. Take the time to learn when you are most productive and cluster your work tasks into that time window.

You’ll find that you are more productive if you play to your natural rhythms.

Consider these questions:

Are you a morning person or a night owl? Are you most productive settling in for long, uninterrupted sessions? Or do you thrive when you take regular breaks to refresh your mind? Working within your ideal circumstances will ensure that you are as productive as possible with as little effort as possible.

So, take the time to figure out what the most productive version of you looks like and schedule your days accordingly. Set yourself up for success by working with your natural productivity cycle and style.

Accomplishing more work, faster, will leave you more time to do what you want to do.

Schedule your life. Use your schedule to annex off time for your personal life as well as your business obligations.

It’s easy to say that you want a better work/life balance. But, in order to achieve it, you have to treat personal appointments with the same respect and value that you give your work time. Writing all obligations on your calendar will increase the likelihood that you’ll keep them.

This tactic also allows you to see how you are spending your time.

If you find that you’re not making enough time to exercise, relax or socialize, you can make more informed choices as you schedule your next week.

Challenge #4: You Wear ALL of the Hats.

Congratulations! You’re self-employed!

You thought you were signing up to be the boss. But chances are that you didn’t anticipate that you were also signing up to be your own marketer, salesperson, human resources manager, customer service rep and… well, everything.

When you’re self-employed you often have to wear all of the hats.

This means you’ll find yourself tackling tasks (like office management, reporting and data analysis, IT support and accounting) that you may never have thought would be a part of your job description.

And, yet, that’s the reality of being your own boss.

Steve Tobak, entrepreneur and author of Real Leaders Don’t Follow, may have put it best when he claimed an entrepreneur is the “chief everything officer.” As Steve notes:

Maybe your passion is marketing, accounting, recruiting, engineering, design, web development or cooking. That’s nice. Now you get to wear all the hats… Running a business is harder than it looks.

Not only do you play every role, you also set the direction and choose every step your company takes. When you’re your own boss, you have a hand in every choice and every task. So how do you do it?

Your Success Hacks.

Accept that you’re a student, too. As an entrepreneur, you’re going to need to learn a lot of new skills. So, check your ego and embrace the journey.

Don’t know the legal ins-and-outs of hiring an employee? Learn them.

For example, here are 10 legal mistakes that can destroy your new business and how to avoid them:

Not sure what a landing page is or why you need one (or many)? It’s time to find out.

The silver lining is that there are so many resources available that you can take advantage of. You can start with the old stand-by (books). But, don’t forget about podcasts, webinars, Youtube (here are 15 must watch YouTube Channels for Entrepreneurs and Small Business Owners), and entrepreneur networking groups like the Entrepreneur’s Organization.

Seek out information wherever you can find it.

For example, there are common myths about starting a business. Know them and learn why they’re untrue.

Build a complementary team. When you start hiring employees make sure that you bring on teammates who are strong where you are weak.

When you’re your own boss, you often have to be all things. But, if you can find a team to support you in the skills you know you lack, your company will be stronger for it.

That also means you’ll need the self-awareness and honesty to acknowledge where your weaknesses are.

So, once again, check your ego and give yourself a good hard look.

The better you know yourself, the better equipped you are to make good choices about how to spend your time and what tasks to delegate.

Celebrate your talents and strengths! And, then start working to shore up your shortcomings.

And learn how to lead. Leadership is a skill you can master.

The Dream is Worth It.

There’s no doubt that starting your own business and being your own boss comes with many challenges. But, few decisions can have such a tremendous impact on your life.

Not to mention, that it can also be one of the most rewarding things that you’ll ever do.

Jeff Cates, president and CEO of Intuit Canada, reveals that:

Four in five small business owners said they now have greater life satisfaction than they did before, and 65 per cent actually feel less stressed than when they worked for someone else. To this end, only 17 per cent would ever consider working for someone else again.

And you’ve already gotten a sneak peek into the dark side of entrepreneurship.

You can become your own boss prepared for the obstacles you’ll face and armed with the tools to combat them.

You’ve got this.

If you want to be your own boss, take the next step and get a new company name, a new logo design or a website design. Crowdspring’s community of over 210,000 graphic, web, and product designers can help you achieve your business dreams with a fresh design – without breaking the bank. You can get started on a project here, or request a free, no obligation design consultation with one of our design experts. 


Katie Lundin is on the customer support team at crowdspring, one of the world’s leading marketplaces for crowdsourced logo design, web design, graphic design, product design, and company naming services. Katie helps entrepreneurs, small businesses and agencies with branding, design, and naming, and regularly writes about entrepreneurship, small business and design on crowdspring’s award-winning small business blog.