5 Tough Lessons I Learned The Hard Way As An Entrepreneur
Being an entrepreneur requires exceptional leadership skills, creativity, and resilience. If you didn’t grow up around other small business owners and didn’t go to business school, then you might have jumped into running your own business without knowing some key lessons that are essential to long-term business success.
When I started my entrepreneurship journey I had zero clue what I was doing. I knew I was a fantastic digital marketer — but I quickly found out the skill you are good at is completely separate from the skills needed for running a business.
All I knew was that running my own show was the only way I was going to create the life I wanted to be able to put my priorities first. And like many lessons in my life, I had to learn them the hard way.
So today I’m sharing the most impactful lessons I learned as a work-from-home business owner that I wish someone had told me.
01. Not everyone is your client, and that's okay
I think most people who start a service-based business go through the phase where they will take any work just to pay some bills and get going. It's easy to get caught up in the idea of catering to everyone's needs but trying to please everyone will only lead to burnout and the dilution of your brand.
Sometimes you’ll only realize a certain type of client or service is not right for you after you are knee-deep in the work. It’s going to happen.
The important thing is to recognize it, correct it quickly and professionally, and move forward.
This lesson might be the hardest one I had to learn, in that when I realized I had to fire a big client, I had let them take over most of my time and business, and I ended up letting go of 60% of my income. You can read the story about that client and niching my services here.
Here are some tools I developed over the years to help me only take on great-fit clients:
I niched my services to only offer what I loved doing.
I required potential clients to fill out an application (which helped me sort bad-fit clients most of the time) before they could book a discovery call.
Even if they slipped through the application and onboarding process without red flags, if those red flags became obvious I gave myself 60 days to do my best to correct the issues with the client or let them go.
I analyzed as best I could what it was about my favorite clients that made them such a great fit and tried to weave that verbiage into my marketing.
02. You don't have to build and market your business the way everyone else says to
There’s only one thing you HAVE to do in business — and that is you have to market what you’re offering or no one will know you’re open for business.
After that, how you choose to create your marketing plan is wholly up to you.
I started my business because I had a few years of being the social media manager for the band Megadeth under my belt (you can read that story here). I knew I had a knack for digital marketing and wanted to help my peers with my skills.
But social media marketing back in 2012-2015 was the wild west. There were no expensive courses or scheduling apps or anything else that makes marketing easier to manage a decade later.
And while apps, platforms, and trends have come and gone over the years, the fact is, there's no one-size-fits-all approach to building and marketing a business. What works for one “influencer” or that buzzworthy mastermind program may not work for yours. It's crucial to experiment and find what works best for you.
When building and marketing your business, it is essential to stay true to your vision, values, and personality (if you’re a solopreneur). Don't be swayed by what other brands are doing or what industry experts recommend.
In fact, the best, most creative ideas for social media campaigns came from inspiration totally outside the music industry — not from following what other bands and artists were doing.
Your marketing (and hence how you build your business) should hit these checkmarks:
you enjoy using and posting on the platform(s)
your ideal audience is also on the platform(s)
your branding voice and visuals are clear and consistent
you have a system for batching your content marketing so you don’t have to be creating it all the time
If you are like most business owners and struggle with creating and being consistent with your marketing, check out the Marketing Magic App. This amazing AI-powered software merges your brand with all the marketing assets you need to create for your business (I’m an affiliate for this amazing tool that makes every marketing task easier).
Right now you can sign up for a free trial to take a spin around what the Marketing Magic App can do.
When you sign up for a free trial, you'll be able to...
Create a short sales page in 2 minutes
Craft a marketing email in less than a minute
Create a product description for your website in moments
Craft an Etsy listing including tags & keywords
Draft 24 social posts to promote your product
The best part is, “free trial” doesn’t mean you try it for free for a week and then get charged. You have access to test out the trial version as long as you want to see what this brilliant software can do, and no credit card is required.
03. Shiny object syndrome is real - have a system for gut-checking
As an entrepreneur (especially if you’re online-based), you will come across many opportunities that may seem too good to pass up. Ad targeting by social media platforms has reached a level of creepy based on your activity, and you’re probably in an echo chamber of your peers who are also looking to solve similar problems and are on the same email lists of the big names in your industry.
It's easy to get distracted by these shiny objects and lose focus on your business's core objectives. It's essential to have a system for gut-checking these opportunities. Ask yourself if it aligns with your business's mission and values and if it will help you achieve your long-term goals. If the answer is no, it's best to pass on the opportunity and stay focused.
Often times we think signing up for the latest course, program, or app is the key to solving all our problems in building our businesses — but the reality is we usually need to focus on follow through instead.
Here are the 5 questions to ask yourself before you decide on buying the next shiny object:
Do I already have a solution available?
Am I avoiding something?
Would my future self/business be doing this?
Will this actually save me time and/or money?
Am I spending more time planning than doing?
This problem is so prevalent in the entrepreneur world, that I wrote a whole blog on dealing with “shiny object syndrome”. You can read more about each question to ask yourself here.
If you want to be more distraction-free in life and work (and get your hands on my shiny object decision tree flowchart), grab the Distraction-Free Living eBook
04. Find a peer you can bounce ideas off of and share your real struggles/wins - with no expectations of leverage
Being a work-from-home CEO can be lonely at times. It's crucial to have someone you can bounce ideas off, and share your struggles and wins with. However, this person should be someone you trust and who has no expectations of leverage.
It's not uncommon for people to want to leverage their relationship with each other for connections and personal gain. Having a peer who genuinely cares about your well-being and success can be a game-changer.
Helping each other with accountability and fresh perspectives are what are going to help you make better business decisions.
Shiny Object Syndrome is one of the lessons I have struggled with the most in growing my business, and my own “biz bestie” has been an invaluable help in offering insights into this lesson. I asked her to be a roadblock for me every time I got sucked into wanting to try or do something new. Not only do I have to sleep on it before I click buy, but I have to chat with her about it first.
We’ve been biz besties for over 8 years now, and so she knows me well enough to see my blindspots and how I think. I can honestly say if it wasn’t for this relationship, navigating the years of pivots and income roller coasters would have been much tougher.
If you’re looking for that peer relationship, the best advice I can give is to just be open to it coming to you. Don’t try to force it and be patient with how that relationship unfolds.
05. You will never get through your to-do list - prioritizing skills are key
Ask any professional adult if they feel like they “get everything done” and they will tell you that the to-do list never ends. If you add in being a CEO, parent, partner, or any of the other wonderful roles in life — and you can count on experiencing the feeling of no one getting the best of you and a million half-done projects taking up space in your brain.
As entrepreneurs (especially solopreneurs), we can get bogged down in menial tasks in order to feel like we’re checking things off and making progress. But there will always be something that needs your attention — from email pings to client needs and product launches.
You have to create boundaries around your priorities if you’re going to achieve your goals. And since you’re the boss, it’s your job to do so.
One of the best tools to create those boundaries is what I teach in my Theme Day Planning Method. Flexible time blocking will give you enough time to get in the flow state with a single project or task that will move your business forward.
And boundaries are not just for work! In order to be well-balanced CEO, you have to take care of yourself and any other priorities in your life (like your family or a hobby you love). When you realize you are not a machine of productivity, and you need to fill a few different cups in your day to be happy and healthy, all those tasks that don’t actually help your business get cut out.
Here are a few questions to ask yourself to help you identify priorities so you can start to create boundaries:
Is this essential for my health (i.e. sleep)?
Is this essential for my relationships (i.e. family time, date night)?
Is this essential for business income and is it going to “move the needle”?
Is this a goal for my own personal development (i.e. hobby, class)?
Theme Day Planning Method will show you how to identify and actually plan for all the priorities in your life, as well as helping you create boundaries so you can focus more.
Conclusion
I wouldn’t trade being an entrepreneur and the control it gives me over my life and destiny — but the lessons I’ve learned along the way have been hard-won and helped me mature into a better business owner. If you’re newer in business, or taking on a new role as a CEO, knowing these five things can help you be better prepared for the challenges that lie ahead.
Here are those 5 lessons again:
Not everyone is your client, and that's okay
You don't have to build and market your business the way everyone else says to
Shiny object syndrome is real - have a system for gut-checking
Find a peer you can bounce ideas off of and share your real struggles/wins - with no expectations of leverage
You will never get through your to-do list - prioritizing skills are key
Remember to stay focused on your core objectives, stay true to your vision and values, and prioritize tasks effectively. With the right mindset and approach, you can lead your business to success.
