How to Survive the Ups-and-Downs to Succeed as Your Own Boss

To succeed as your own boss often seems like an up-hill battle. There are many ups-and-downs you’ll face and it can feel like you won’t be able to survive them all.

How do I know this? When you’re self-employed you experience major peaks and valleys. Self-employment isn’t easy.

When you work for yourself you tend to question everything you do. From interacting with other people on social media or working with clients, it seems that everything you doesn’t come out right.

It can feel as if you’re in a constant state of hustling and for what?

Once you finally feel like you’re seeing good results, they either stop happening or you have to let go of a passion project because it just doesn’t make sense anymore.

The hustle is never-ending, that is until you set boundaries!

You have to learn how to become a business owner who can survive this crazy roller coaster ride. Sometimes it can feel like all that hustle was for nothing.

I know you can you relate!

The continuous cycle of running a successful business can be frustrating and discouraging. But you can’t give up (reminding myself of this right now!).

There are specific steps you can take to not only survive the success of being your own boss, but learn to thrive in the midst of ups-and-downs.

Here are simple steps you can take to regain control of your business.

1. Remember the successes

Oh how easily we forget how far we’ve come and how much we’ve accomplished along the way. Once a goal is reached there are a hundred more lined up after it.

This dissatisfaction with your accomplishments is the root of the problem. You forget the success you’ve had and the big goals you’ve already achieved.

I am SUPER guilty of this mistake and it’s something that can keep me down in the dumps for weeks.

How do I get past this negative habit? Write out all of your successes every single week — or even at the end of every day.

Jot down your achievements:

  • List out at least 5 big things you achieved this year! And then be thankful for each one of them. Remember your successes and don’t let the pressures of other bloggers, business owner or people on social media get you down.
  • Create a habit of positive focus every week. At the end of each week I spend time writing out my accomplishments in my “success journal”. It’s a simple Moleskin journal that details everything I got done that week, from big to small. This is a good reminder to focus on the positives instead of obsessing over the negatives.

2. Consistently prune your project list

When I was going through business depression at the beginning of 2015, I discovered that I had gotten way off track from my original purpose.

It’s waaaaaay too easy to get sidetracked by the amount of money you can make, or outside advice other people offer you because they’re “just trying to help”, or successful case studies that have worked for other biz owners.

I learned the hard way, how vital it is to constantly prune your list of projects, clients, and services.

This routine check-in is what you need to stay on track with your financial goals, and make sure you’re still doing what you love.

Sit down and prune your project list on a monthly basis. Although, I still do a big purge every quarter where no one, and no project, is guaranteed to make the cut.

Create a project comparison list:

  • Use a large notebook or sketchpad (or use my spreadsheet template) and draw multiple columns down the page — one for client/project name, price, hours involved, enjoyment level, and notes. This is really fun to do this with colored pens or markers.
  • Write out the project details in each column. Don’t worry about what order they’re listed in, you’ll rearrange them in the next step.
  • Arrange them from best to worst depending on which category is a priority for you. If it’s pay you’re worried about, then list your projects based on pay rate. If it’s time or energy level, then categorize your list based on which projects you dread the least? Arrange your least favorite, or lowest paying clients, towards the bottom, with the other more prominent clients at the top.
  • Draw a red line and cut any projects that fall below your expectations. Anything you feel isn’t worth the time, headache, energy, or money anymore needs to be removed. Remember, this exercise is about growing as a business owner, and in order to do that you have to prune until it hurts.

Once you’ve finished doing this, take a step back and look over everything. Are there any surprising things that bubble to the top? Did one client become your absolute favorite?

Subject every project to these questions:

The first time I did this, it was shocking how effective the process was when I saw everything in black and white.

Here are 5 questions every client/project on the list is subject to.

  • Do I still enjoy the work, or do I dread it?
  • Do I like working with the client?
  • Am I paid on time, with little headache?
  • Does the project excite me?
  • Am I paid a price that’s fair? Do I feel well compensated?

If any of the answers to these questions is NO, then I consider cutting them from my workload (and suggest you do the same).

This means letting the clients know you’re either raising my prices, won’t continue doing the work until you get paid, or can no longer work with them.

Once a client is no longer on your list, you’ll have time slots open to add in more projects or work that you do enjoy, or that pays wells.

This is a process that keeps a business growing, and can help you stay on top of all your work.

I highly encourage you to carve out time this week to create a project comparison list. If you don’t want to do it on a notebook or sketchpad, I’ve created a free client comparison spreadsheet template you can use and customize for your own biz.

3. Make your work the number one client

Working with clients can be a very lucrative way to build a business. In fact, Alexis Grant has built a social media marketing business that employs 8 team members.

And I too employed several team members while I built the Careful Cents community on the side. The only thing about this though, is that you must freelance as a way of bringing in revenue until you can work for yourself long-term.

What does this mean? Your bank account is subject to someone else’s payment schedule.

You’re still working for someone else to pay the bills, and that can lead to being trapped in the employee mindset again.

Your own business should be your number one client, and receive top billing hours. As your own client, you don’t have to depend on someone else to get paid on time, and you don’t have to worry about being fired.

The work you do is sustainable, consistent, and has the potential to make a lot of money.

Don’t believe me? This is something successful entrepreneur, Chris Ducker teaches — build the business of you — so if it works for him, I know it can work for you and I.

Take the challenge:

Putting your own brand in the number one client slot allows you to have more control, and freedom, over how much you work, and when you get paid.

  • For the next 14 days, I dare you to make your own blog and biz your NUMBER ONE client. Give your business prime time at the beginning of each day. What’s one project you’ve been dying to work on? What’s a blog post topic you’ve been meaning to write for over a month? Take these ideas and carve out time each day to work on them (even if it’s 15-30 minutes). No more trying, now it’s time for doing!

I’m already doing this experiment right now, and have spent the past six months working on Careful Cents projects for the first hour of each work day.

My goal is increase my traffic and income to fully fund my lifestyle. It’s a small, very attainable goal that’s not overwhelming for my schedule, and I feel confident I can do it.

4. Create a smart portfolio of work

There’s a difference between entrepreneur ADHD (yes, it’s a real thing!) and creating a diversified list of work as a business owner. Your goal is keep your “shiny object” distractions to a minimum and determine which ideas are worth pursuing.

Since being my own boss in June 2011, I’ve called myself many things.

I was a social media manager, marketing strategist, newsletter content marketer, business and tax consultant, freelance writer, assistant editor, and managing editor.

Although that’s quite a diversified list of job titles, all of them were unified because I chose to work with startups, bloggers, and companies related to the finance and business space.

This allows me to become more focused with my work and reach my target clients better. I get to work with awesome brands, like QuickBooks Self-Employed and Focuster.

I also have a plan for bringing in more affiliate income, and possibly adding more consulting clients to my list.

The point is to look at where your income is coming from and find out how you can diversify it more.

Diversify your portfolio:

  • Are there brands you can work with to promote helpful products?
  • Can you do in-depth tutorials and reviews that produce a portion of affiliate income?
  • Can you offer coaching or mentoring programs?
  • What can you do to branch out your list of offerings and create more income streams?

When putting money into traditional investments, you have to diversify your portfolio in order to mitigate risk, and make sure you aren’t setting yourself up for failure by depending on one stream of income.

The same rule applies to being an online biz owner.

This will also make working something you look forward to doing, because you’ll never get bored of what’s on your plate.

Click here to find out how to use Pinterest to create a free portfolio of work.

5. Create a future-proof business

The biggest lesson I learned while trying to level up my business, is that I have to stop trying to put bandaids on my business to fix it in the short-term.

To succeed as your own boss you have to create a future-proof business that can stand the test of time. Cutting back on client work is scary, no doubt, but when done the right way, you can double your income in half the time.

Seriously! In the past, I’ve personally used the tips mentioned here to see great results.

I removed a client from list who was paying me $25 an hour for 30 hours a month, and replaced it with another client who’s paid me $44 an hour for 16 hours worth of work.

“Leap and the net will appear.” – John Burroughs

Don’t let your hard work be at the mercy of clients who might fire you tomorrow. Put your own blog/business on the list of clients you serve and make your projects a priority.

Strive towards building a future-proof business that doesn’t drain you of joy and energy but instead, replenishes it.

Then put these other strategies to work and create a long-term strategy that will take your business to the next level.

If you want to succeed as your own boss, take one action item from this list and implement it in your business this week!


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