I'm Esther!


I'm your work-from-anywhere mentor & cheerleader. I’m a former Googler turned freelance marketer and mindset coach, building my dream life, at home and abroad.


15 Things No One Tells You About Working for Yourself

Do you have dreams of working for yourself? Discover what no one tells you about self-employment and what’s beyond big dreams and hard work.


15 Things No One Tells You About Working for Yourself

February 23, 2022

Do you have dreams of working for yourself? Discover what no one tells you about self-employment and what’s beyond big dreams and hard work.

Do you ever fantasize about working for yourself and being the star of your own Instagram fantasies? We’ve all seen the filtered photos of corporate burnouts who are now working by the pool in Bali before meeting up with their business mastermind group. Or the IG moms who are somehow building a branding empire and crushing it as a business owner in between soccer practice pick-ups. 

You can have big, audacious goals and realize that same success and more when working for yourself, but there’s so much more to it than the lifestyle that comes with it. Building up your career and lifestyle to harmoniously coexist takes time and hard work to finesse. Is it all worth it? Absolutely. As someone who left the golden handcuffs of the corporate rat race, started my own freelance marketing business and made nearly $250k a year in my first year as a solopreneur, I can say without a doubt: Yes, it’s all worth it.

Despite the rewards, there are some challenges along the way that no one really talks about. Here are 15 things no one tells you about working for yourself, dreaming big, working hard, and staying focused.

Everything you need to know if you want to start working for youself

1. You’ll work crazy hard at first.

You’ll inevitably work crazy hard and put in some serious hours to get your business off the ground. The truth is you’re going to end up working more than at your 9-to-5 job at first. 

Don’t worry; there is an upside. This time you’re working for yourself and building your dream life and business, not stuck at a mediocre job, feeling burned out. You’re also in more control of your schedule so you can travel or spend more time with your kids if you put your mind to it. 

2. You’ll be wearing ALL the hats in the business at first. 

Don’t expect to embrace those four-hour workweeks anytime soon. When you launch a business, everything is your responsibility. You might as well embrace the parts that suck and watch your business grow due to your hard work and persistence. When you’re a multi-tasking business owner, you’re suddenly tasked with playing:

  • Entrepreneur
  • Technician
  • Admin
  • Project manager
  • Account manager
  • Customer support
  • And so much more…

The bonus is that you can design your day the way you want and on your own terms. You’ll definitely be working long hours at first, but you also don’t need to be chained to a desk all day like you were back in your 9-to-5 days. Focus on being intentional with your days and make your schedule work for you.

When I started working for myself, I focused on time-saving hacks like scheduling client meetings all in one day or batching work. Choose a day to tackle your admin work one day and your creative brainstorming and content creation on another. Or find the times of day that you feel energized and refreshed to dedicate the most challenging tasks. 

However you structure your day, be sure to get outside at least once a day (I know that sounds silly, but sometimes we need reminders!). Force yourself to get out and go for a run, walk the dog, or grab a coffee down the street. It may sound basic but is crucial for your mental health.

3. You’ll need an amazing morning and daily routine.

When you first start working for yourself, it’s tempting to skip over your morning routine. Keep in mind nearly every successful entrepreneur is disciplined and routine-oriented. The sooner you learn this, the better. 

Your morning routine can blend some stretching, brainstorming, mediation, exercise, reading business books, or anything else that helps you get your day started on the right foot. I’ll do a whole blog about morning and daily routines in the future, but you need to commit to self-improvement from the start.

You may find you have enough discipline to get started, but continuous self-improvement is a must. Refining your craft to become the go-to in your field may require some additional support to help you chart the path, and more importantly, stay on it. Get yourself a business coach, or start devouring self-improvement and business books to empower yourself to keep going.

4. You’ll have to get SUPER comfortable with selling yourself.

You can be the most brilliant copywriter, social media manager, branding strategist, or web designer on the planet. But if you won’t go out there and sell yourself, you’ll fail. It takes trial and error when you’re growing a business and asking for the sale, but there’s no way around it. Through repetition and refining your approach, you’ll get comfortable with the process. The alternatives are awkward client meetings and a dwindling bank account, so you might as well embrace it.

There are other issues around being uncomfortable with selling. You may be able to get through that discovery call with a client but ultimately lowball your own prices. This is a sign that you’re afraid of failure and don’t know your own worth in your business and how to sell it. It’s far easier to deal with the discomfort of selling yourself than trying to raise your rates later. If you know you do excellent work that delights your customers, there is no reason not to price your services accordingly.

Doing competitive research to see what similar businesses are charging is a good way to know what the market will bear. If your price makes you super uncomfortable, it’s probably too high or too low. And if your price makes you excited but a little awkward, then it’s probably just about right. You may get a few no’s along the way, but that’s normal. And they’re likely not your ideal clients if they can’t pay the rates you deserve.

Remember that selling yourself isn’t dirty, it’s about offering value. It’s also not about convincing someone that you are the most talented and experienced person on the planet for the job. It’s about showing potential clients that you understand their unique needs, can solve their problems and that you deliver on quality and value to make their lives and business easier. Remember, your ideal customer wants what you’re selling — that’s why they’re considering hiring you. All you’re doing is making them an offer to help, which they will happily take you up if you can deliver what you’re promising. 

5. Your network will become more important to you than ever.

Entrepreneurs and small business owners talk about the importance of networking for good reason. It works. But how do you actually network while working for yourself? 

Warm up your social media contacts and inner circle and let them know what you’re up to and your new business plans. There are also endless networking groups you can join locally or online. Look for groups to generate leads, connect with like-minded business owners supporting each other, and thought leaders who offer tips on growing your business. The entrepreneur and small business community is incredibly vibrant and so essential to tap into.

Referrals are also the lifeblood of any business. If you do amazing work, it’s inevitable you’ll generate a lot of business via referrals. Return the favor by referring others to your network and keep the business karma going. 

At some point, you’ll end up speaking to a potential client that gives you a bad gut feeling. Listen to it. Don’t work with anyone who makes you uncomfortable. You’ll learn this lesson the hard way, but try to listen to your intuition so you don’t have to learn it more than once.

Getting comfortable and trusting clients also means asking for money. Whether you ask for a portion up front or wait until you invoice them for the full amount, it can feel awkward at first. This is normal, but you also need to get over it as quickly as possible. Ask for the money professionally, and as soon as possible. Otherwise, you’re not taking your business seriously, and neither will your clients. 

6. Your family and friends will constantly ask you what you do.

Your friends and family probably have very little experience or understanding of self-employment and how it applies to the real world. Instead of continually educating them, set up a killer, easy-to-understand website, and share it with them. A fine-tuned elevator pitch where you describe what you do and who you do it for in one or two sentences is also helpful. Just remember, you don’t need to justify or explain why you’re self-employed. Approach each conversation with confidence and show your enthusiasm for your new self-employed lifestyle.

7. People won’t take your business as seriously as you do. 

It’s probably not personal, but your partner and kids may not take your new business that seriously. They will also still have the same expectations of you from when you worked your 9 to 5.

It’s common for people to assume working for yourself comes with optimal flexibility for the family: “Why not just throw in a load of laundry if you’re working from home anyway? Could you start dinner? Or pick up the groceries? Will you be the one to stay home with the kids when they’re sick? Or run the errands?”

Set boundaries with your loved ones and remind them that you’re still working from the very start. If you do agree to tackle one chore a day or being the go-to for a particular task, make sure everyone else around you knows what your limits are. Your work is just as important as theirs is and requires dedication and commitment. 

8. There will be mindset shifts.

Starting your own business, freelancing, and changing your lifestyle come with a mindset shift. With few exceptions, you’ll need to resist the urge to share all the personal details about your family with your clients. They may be understanding, but you don’t want to give the impression you can’t complete your work or are a stay-at-home mom with a hobby business. Sure, you should be friendly, but keep it professional. 

There are also personal mindset struggles. You’ll struggle with the mindset of not being enough in your business or in your home life. There are only so many hours in the day. And sometimes, you’ll feel like you’re playing “business” instead of actually owning it.

Your mindset shift may also change depending on the season. One month you may feel like you have your work-life balance nailed down, and other times you may lose yourself in your business. The fluctuations can feel destabilizing, but it’s also normal to occasionally wonder if you should have stayed in a secure day job where you could leave work at work. Of course, on that next sunny day where you get to finish up early with a delighted client and go on a hike, you’ll remember why you chose this life.

9. Downtime suddenly disappears.

You’ll have almost zero downtime at the beginning of your new work-from-anywhere lifestyle. Your family life and business are all you’ll have time for, especially when you’re trying to get your new business (a.k.a. your new baby) off the ground. This is normal in the beginning, but you need to keep going. It won’t be long before you see the light at the end of the tunnel and find more balance.

It can also be challenging to travel the world while working for yourself but is well worth the trade-offs. Why not work from Bali or Australia for three months? You may be working indoors on a glorious day while your family is outdoors, but then reap the rewards of having several days off to explore and earn more money. You also have the sense that you’re in control of your time and destiny.

Wherever you’re working from, you’ll realize you love your business and your work. Taking it with you on the road can be an exhilarating experience where you realize you’re living the dream. It can also be incredibly rewarding to know you can be flexible and not miss those big family moments when you’re in control of your own schedule.

10. Your sense of urgency skyrockets.

You’ll probably have the strange sensation that every single moment holds urgency. Suddenly you know exactly what you can accomplish in 45-minutes during cartoons or 90-minutes during your kid’s naptime. Waking up at 5 am to work on your business before heading to your corporate job suddenly feels productive instead of exhausting. If you have difficulty with focus, you’ll find you suddenly have more of it. It’s suddenly easier to hold your focus and sense of urgency when every minute counts.

11. You’ll feel really alone.

Unless you have a business partner (and even if you do),  things may feel really lonely at first. People won’t understand what you do or why you’re not socializing as much as before. It’s also lonely going on this exhilarating, transformative journey when it feels like the rest of the world around you is standing still. 

People don’t usually understand the work involved in running a small business. They probably think you’re at home watching Netflix in your PJs. And that’s fine. Just remember, other people’s opinions about you are none of your business. Ignore them and continue to focus on your growing business on your own terms. 

Instead of feeling the loneliness burn, go out and create the support system you need. Consider joining a co-working space and going in a few times a week so you get some human contact. This can also be a good place to set up meetings with other team members or even clients.

12. You’ll want to indulge in confusion.

Spoiler alert: don’t give in and don’t panic! You can figure anything out. Write it down, put it in your phone, or set a daily reminder for yourself so you never forget that you can figure it all out. Journal it out in the mornings and examine your thoughts. Pretty soon you’ll notice that most of your anxiety-riddled thoughts are not grounded in reality – they’re just your brain trying to keep you safe and in the status quo. But you can think new thoughts that help push you forward towards where you want to be. 

Here’s what usually happens: You’ll have to make a million decisions a day, and you’ll be tempted to say ‘I’m confused’ to avoid making a decision. Don’t do that. Make the decision, see what happens, and then move forward. You can always make a new decision if your first one didn’t get you the result you’re after. 

If you fail, that’s actually a great thing. It means you figured out a way to do something that doesn’t work. Remember what Thomas Edison said, “I have not failed. I’ve just found 10,000 ways that won’t work.” Of course, succeeding is also a reason to celebrate but means more than just securing the gig or the next payday. It means you learned to trust your judgment and become even more efficient with decision making and indulge less in confusion.

13. It’s tempting to never leave the house (or your yoga pants)

Yoga pants are a wonderful invention, and it’s far too easy to stay in them all day, every day, and never leave the house. Resist the urge! Otherwise, it becomes like the pandemic: It’s all yoga pants all the time.

Taking off the yoga pants is a way to take care of yourself. While you’re at it, make sure you’re getting rest, some exercise, and work plenty of self-care into your routine. Your health is not worth compromising for even the sweetest of successes. However, it’s not enough to promise to do it or squeeze it in when you have a few moments. To take care of yourself, you must schedule it. Guard your time and calendar aggressively to ensure you have the downtime, care, and daily habits you need for a healthy life. 

14. You’ll want to quit.

Working for yourself can suddenly feel less than attractive. That feeling of giving it all up to retreat back to your old way of life is bound to happen. It’s also normal to have some mishaps along the way. There will inevitably be a bad fit with a client, mistakes, or the realization that a particular product or service you’re offering isn’t in your zone of genius. 

You’ll need to make changes, pivot, and try again. And often, it will make you want to throw in the towel. The desire to quit and run for the hills will probably come up more than once. Don’t do it. As long as you don’t quit, you cannot fail. Failure is a choice. As long as you are learning, you aren’t failing. Just keep going!

15. You’ll never want to go back to a 9-to-5 again.

You’ll learn there’s nothing more satisfying than having control over your own career, time, schedule, and income potential. If you can make it through the first couple of years, things will get easier as you gain confidence in yourself. Soon you won’t have to dig deep for the courage for every single new thing you’re doing. You’ll know you have the skills and experience to get the job done, and that will give you confidence. And the more money you make that proves you’re doing it, the more you’ll realize you’re living the life you always wanted.

What no one tells you about working for yourself

There’s no doubt that working for yourself is a challenge, but it’s so worth it. If you want to earn more, have more control over your life, and build your dream lifestyle, your day job won’t get you there. It’s time to get out of your comfort zone, embrace the bumps in the road, and pursue that path to work-from-anywhere self-employment that you’ve been searching for.

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What you need to know about working for yourself

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I'm Esther, your
work-from-anywhere mentor & cheerleader.

I’m a former Googler turned freelance marketer, business mentor and mindset coach, building my dream life in Southern Spain.

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