Critical Business Lessons I’ve Learned (How to Avoid Disastrous Startup Mistakes)

The judgment, the comparisons, the rejection— Entrepreneurship is not for the faint of heart. And neither is opening up about the experiences you’ve had along the way and the many, many, many business mistakes you made. (And when I say “you”, I really mean “me”.)

But I’m here anyway, sharing my journey in the hopes that you’ll not only learn from my past mistakes, but that these business lessons will provide you with the tools you need to prosper. 

 

Whoever you are — whether you’re a current or former client, a past colleague, an Instagram follower, or you simply stumbled upon this post — I’m happy to have you here.

My goal in writing this post was to inspire anyone who needs help letting go of whatever’s holding them back in business. And, in the process, to empower you to take bigger, better, and smarter steps in your business. 

In order to do that, I need to take you through my entrepreneurial career, from my greatest mistakes to my biggest wins. And that means sharing with you how I went from employed to unemployed, and then employed again. But, this time, as my own boss and the owner/creative/visionary of this now-successful online digital marketing business. 

Whether you’re struggling to get your business off the ground, wondering how to survive a misstep or two, or simply want proof that every single person who’s had the guts to start their own business hits a rough patch, my story and the following business lessons are for you.

“Failure is the stepping stone for change and growth, followed by success!”

 

I was getting really tired of working 50+ hours, moonlighting, and catering to external expectations other than my own. Sadly, this was a recurring pattern of mine. 

For years, I felt like I had a bigger role to play in the industry. By late 2017, the noise from all the possible alternatives swirling around my head became too much to bear. 

So, I decided it was time for a change. But what change exactly?

I started with the following question: What had I really accomplished up until that point?

I’d done a lot, it seems:

• I built and ran design departments. 
• I helped my employers reach their financial dreams through hard work and ingenuity.
• I hired great talent that enabled that growth and financial success for my employers.
• I formed strong relationships with fellow designers and shared clients with them. 
• I leveraged my experience in non-profits, fundraising, event management, design, and marketing to strengthen other people’s businesses.

There were two things I realized after I evaluated what I’d done. 

The first was that I was craving more control. Correction: I wanted full control over my professional destiny. 

The second thing I realized was that I didn’t just want to improve my life and business, I wanted to do the same for other people. 

Once I had that realization, it felt like my body and mind were on fire. I needed to take action and I knew it was time to build my own business. I just knew that going down this path was the right one — that the fulfillment and joy of helping others do what they’re meant to do would be greater than anything you or I could imagine.

Knowing that you want to start your own business is only half the battle. Before you jump in head-first, you need to make sure you’re prepared for it. 

Here are some questions that will help you figure out if you’re ready for this life, career, and mindset shift:

• What would it feel like to be accountable to myself?
• What would it feel like to be in charge of my own time?
• What would it feel like to take a risk every day? 
• What would it feel like to work with leaders and businesses who hired me to enable their success?
• What would it feel like to feel free?

Starting your own business is like gambling: You win and you lose. But it’s what you do with those winnings that will define your future and how you handle the losses.

 

Even before I took the leap in 2018, I started doing my research. A lot of it. I found myself dreaming up everything I needed to do:

• Develop branding for myself
• Create a more streamlined process for designing websites
• Build marketing plans
• Start relationship building
• Strengthen my customer service
• Educate teams of creatives
• Create valuable content

I didn’t realize I was laying the plans for quitting my job and starting my new business. I was just consumed by this idea. I was completely obsessed with my work, fired up about learning, and determined to make a change — to the point where I actually began to dream about it at night (during the little bit of sleep I was getting). 

Within just a few months, I made the biggest decision of my life. 

I didn’t try to do it alone though. I went in search of support. 

I emailed influencers, leaders, businesses, and past connections on a quest to make baby steps towards creating a business I could sustain and live off of on my own. 

I emailed business coaches, mentors, project managers, virtual assistants, copywriters, designers, web designers, you name it. I desperately wanted validation that I was making the right decision.

Plain and simple, I was seeking acceptance and was yearning for community. A place where I could feel heard, to talk about my business frustrations, and to keep myself accountable for a goal I wanted so badly. 

If you’re like me, you need to be surrounded by good people who are positive and uplift you. You need community, too.

So, here’s what I did:

• I hired coaches.
• I hired a business manager.
• I enrolled in a new course that had a solid community.
• I joined numerous Facebook groups.
• I signed up for a conference.
• I signed up for any free program or resource I could.

By the middle of 2018, I invested $10,000 in professional development (AKA figuring shit out). 

I didn’t go into debt to do it. I saved up 6 months of my salary before I quit to take my business full time. It was enough money to know I would be comfortable while I built my business. 

By the way, I strongly advise against going into debt to grow your business. If that’s your plan, you need to re-evaluate your strategy.

Some of the people I hired in the early days of my business were helpful; some were not. Sadly, there’s not always something to be gained when you hire and then lose a contractor or employee. 

To help you find the right people for your business, here is some honest advice: 

Figure out what your rules of engagement will be. 

When hiring contractors, you can’t dictate things like where they work from, what tools they use, or even when they work. So, you need to find people who align with your approach. 

Make sure you know what that is: 

• What hours do you plan to work? 
• How accessible do you want to be and will you set limitations on days/times when clients or team members can contact you? 
• How quickly do you respond to messages?

Don’t be afraid to ask these questions when talking to prospective hires. They’re curious about the same thing. 

Know exactly what you need from your new hire or contractor. 

For instance, if you pay them $XX/hour, what is the deliverable you expect in return? If you can’t clearly explain what you need from them to yourself, you’re going to set the wrong expectations for them. 

If the job and expectations aren’t clear from the get-go, you could end up with a wrong-fit hire and/or someone who just can’t meet or exceed your needs. 

Find out what others have to say about them. 

Look for written or video testimonials from others who have used their services before. Even if you’re not hiring them as an employee, treat this part as if you are. They’re working for you, after all, so make sure their work and level of professionalism is up to the standard you need.  

Don’t be afraid to take it a step further and contact the people who left the testimonials and hear what they have to say!

Do your research on them. 

Everyone has a digital footprint these days. Go to their website, their blog, or their social media and check on their content quality! 

1. Do they provide knowledge and education to their community? Or is it all about them?
2. How do they connect with people? Or does their business appear to be lifeless?
3. Do they care to share their insight? Or are they less than generous with their time and knowledge?

You can tell a lot about someone’s values by the content they create.

Get them on the phone. 

Look beyond the shiny exterior. Just because they seem planned out on social media or they have a rockin’ website, doesn’t mean they know what they’re doing! People are good at bullshitting. Trust me.

Jump on a call with them. What does your gut tell you?

 

Around the summer of 2018, I decided to quit working 40 hours a week for one company in order to pursue my own digital marketing business. 

This isn’t the first time I’ve been unemployed, but this was the first time it was my decision. 

I was so excited to branch out on my own and the few months of unemployment were good for me. The way I was working previously was too much for me to manage and I was really struggling to meet the extremely high expectations I’d put on myself in that job. 

I’m really grateful that I had that time off between my last full-time job and kicking off my new business. It allowed me to get really honest with myself. 

During that time, I realized that I love change so much that I need to constantly be challenging myself and evolving and in control of my surroundings. Which meant I couldn’t work for one company anymore. It also meant that I had a clearer vision for my life, which would make decision-making for my business a whole lot easier. 

Let me say that the decision to quit my job and pursue my dream didn’t happen overnight. It actually took 4 years to gain the courage to take the leap. 

While I regretted not doing it sooner at the time, hindsight is 20/20 and I realize now that I wasn’t quite ready for it.

 

The summer ended and I wanted to quickly get moving on my business. The only problem was that I didn’t think about the most important factor: 

My finances. 

The passion and fire I have for what I do took over! I just wanted to start my agency and push forward without thinking about the money involved and what it would take to get there. 

Unfortunately, I lacked the financial resources to do what I’d envisioned — and it cost me dearly. September and October 2018 totally rocked me to my core. I was drowning.

If you looked at my earnings that first month, you might think that $4,500 was a good start for just leaping into the unknown world of entrepreneurship.

But, the truth is, I had no idea where my financials were and I ended up $2,500 in the red at the end of the month. I overspent without knowing it! 

As I looked back at what happened, I clearly saw the mistakes that I made: 

• I hired people a month into my business and gave away my profit.
• I rented an office space because I thought it would bring me more qualified leads, but never announced it.
• I purchased office equipment I didn’t need.
• I spent energy on people who had no intention of hiring me because I didn’t take the time to see if they were my people.
• I went on a trip that I couldn’t afford and dipped into my savings.
• I didn’t know what my profit was and overspent everywhere.

I had good intentions of growing and scaling, but they were uninformed decisions. I didn’t have a plan for my budget; I just flew into it with passion, drive, and said “I got this!”. 

So, in my first couple of months in business, I made mistakes. But these mistakes became a pivotal moment in my understanding of what wasn’t working for my business and how to get back on track.  

Without risk, there’s no reward, right? 

To give you a little bit of background, I’m a single mom, I own a house, and I take care of myself. There is no backup plan. I am the back up plan. 

Shit has to work at the end of day. So, I made it work.

I knew I needed to figure out the financial side of being in business for myself. I knew that if I didn’t, I would burn through my savings and never understand what was profitable in my business and what wasn’t.

When I tallied up November’s profits and losses, I ended up in the black with $120. I gotta tell ya, it felt like I won the fucking lottery! 

I was so proud of myself for having my first profitable month. And, not only that, I was proud of myself for taking the time to look at my financials, to recognize what needed to change, and then implementing a strategy that worked.

Let me tell you something. I’m a right-brained, creative, free-spirited, intuitive person. And… 

I.

Hate. 

Numbers. 

I really hate them! They stress me out. But numbers are important in business. 

So you don’t make the same mistakes I did, here are the important money lessons I learned from this false start:

1. Review both your personal and business expenses.
2. Set a spending budget based on the revenue you know is coming in. 
3. Get rid of any services or software that you can get for free.
4. Find other service providers or apps if the ones you’re using are unnecessarily expensive.
5. Modify your processes to run without all the bells and whistles of software (for the time being).
6. Know how long it actually takes you to complete a project, so you know how to evaluate which prospective inquiries will be profitable and which will be a loss.

 

I also built a simple spreadsheet to help me manage it all. If you hate numbers like I do, you’ll love this:

This template may help you navigate through your financials and it may not. It works for what I need, but business is not a one-size-fits-all approach.

2019 has been my best financial year to date. In January alone, I had doubled my revenue.  

How did that happen?

Well, I really started to understand where my money was going, where not to invest my time and money, and what to invest in. 

Alternatively, my content marketing strategy was gaining traction and my closing rate was high. I was able to close sales based on referrals, through cold leads to my website, and through social media (thanks, Instagram and Facebook!). 

I also did it organically, so there were no ad fees to cut into my earnings!

7 Critical Business Lessons to Take With You 

If you want to avoid making the same mistakes I made in the early days of my business and double your revenue, listen up. There are a few areas you’ll want to focus in on to get yourself on the right path:

Lesson #1: Pursue What You’re Passionate About

Why are you going into business? Is it because you love making money? Or because you love helping people? 

If you have no urge to help your people and feel no reward when you help others win, why are you doing what you’re doing? I mean that. 

You know when you get to talking to someone and you can tell how passionate they are? That’s how you should feel about your business! Passion and mindset are the two key factors in creating a successful business.

Lesson #2: Be Smart with Your Money

A good portion of my story deals with the money mistakes I made, so there isn’t a whole lot to go into here. I just have a few more points to add. 

If you’re serious about running and scaling your business to success, you’re going to need to invest in it. This is inevitable. So, get good about managing your money on Day 1. 

Then, when you’re consistently in the black, prioritize points of opportunity and capitalize on them. Analyze where your current business income is and set aside 10% for investments you want to make!

Lesson #3: Connect with Your Audience

Find the connection point between the casual browser and the people who’ve loved your products or services. Understand their pain and what drives them to take action to resolve it.

Show how empathetic you are to their plight. 

• Share your real-world experiences with the same pain. 
• Let them hear directly from people who’ve used your services or products. 
• Keep them in the loop when a new project wraps, when your clients’ businesses hit major milestones, and when you have new value-adds to offer everyone!

This will strengthen their trust.

Lesson #4: Be Human

Everyone makes mistakes and visible mistakes are okay. 

For example, there have been numerous times I’ve made a spelling or grammatical error on my social channels while promoting my business. 

This doesn’t happen all the time. However, from time to time it does — usually when I’m too excited to get something out to everyone.

When it does, I openly point it out because this is what makes you relatable. To err is human. So, don’t be too hard on yourself if it happens.

Lesson #5: Your Marketing Shouldn’t Sound or Feel Like Marketing

It’s okay not to have a perfectly curated social media feed. It’s the content you provide to your audience that’s most important. 

A perfect-looking social feed doesn’t cut it anymore. Especially in the health and wellness space, people want to know the real you. So, your marketing strategy needs to come from the heart.

Sharing part of your life and posting content that will benefit your customers’ lives or businesses will go a long way. 

A proper marketing strategy should have your audience engaging with your posts and the way to do that is to give them practical and insightful ways to solve their problems, whether it’s on their own or by reaching out to you.

Lesson #6: Outsource What You’re Not Good At

Do you find yourself trying to learn everything just so you can save money on hiring? The truth is, business owners are all too often the bottlenecks in their businesses and cost themselves more money than all the apps and services and contractors they pay for. 

Psssst! 

Come a little closer so I can share this secret with you… 

The best thing you can do for your business and for your clients is to outsource your weaknesses and stick to your zone of genius.

The only way to grow is to build a team of experts instead of trying to be a Jack-of-all-trades yourself!

Lesson #7: Learn to Be Okay with Saying “No”

If you’re passionate about helping people, it can be so hard to say “No”. Trust me, it’s something I struggle with even to this day. However, I can tell you from experience that it’ll cost you if you don’t master that one little word. 

Here’s how I rationalize it (to myself and to prospects and clients):

If your business doesn’t offer a service, just don’t take it on. The client will respect you more and appreciate your honesty if you say “No” rather than if you say “Yes” and screw it up royally.

So, be transparent. Say “No, but…” and then refer them to partners that you trust. That way, the client gets what they need and you can stay in your lane and do what you’re best at!

 

It’s so strange to look back at the last few years. 

I wanted freedom from feeling guilty about not being at my desk by 8 a.m. every day… Freedom from someone else’s agenda… Freedom to work with people who needed my expertise and know-how… 

And here I am in 2021, living that very dream. I consider myself incredibly lucky that I get to do what I love.

I do want to reiterate, though, that the strategies I wrote about above might not work as well for your business as they did for mine. There are some things that are universal — like managing your cash flow. That’s something everyone needs to master no matter how far you’ve gone in business. 

But there are other lessons from above that might not be the perfect solution for your specific needs or goals. That’s why I work with entrepreneurs, service providers, and other business leaders to build their own success. 

If you’re just getting started out, then I’d love to talk to you about building the right business branding and identity. 

For those of you who are a little more established and want help creating a custom pathway to success, let’s chat about my business coaching and development services.

Book a Call with Ash!