10 Posts for 10 Years: Mistakes Every Successful Entrepreneur Makes

I am celebrating ten years owning my own business! Woohoo. And to mark this milestone I’m sharing 10 new articles reflecting on business insights, experiences and personal stories over the past 10 years. This is the first in the series. Enjoy!

In this article, I share 18 different mistakes that all successful entrepreneurs make. Be sure to read them all. Mistakes are both a cautionary tale and a celebration, often at the same time. Dive in to this long article and learn my mistakes and mistakes by others I’ve met along this decade long journey.

What does success even mean?

I’ve had the pleasure of working with hundreds of women over the past ten years and we’ve had many personal conversations about goals and what we want to achieve. At the root of all our businesses, I’ve learned is that our definition of success is vast and varies uniquely from person to person.

First, we ALL want money

Making an income is a core definer of success for all business people. Whether you want to make enough income to pay your bills or you want to be a millionaire, whether you want to keep it or give it all away, we all need to make money. So, sure, success is defined by making money. How much, how and in what way is part of your success measure too. But, without making money, you are a hobbiest. So we can agree on money as a success marker, right?

Second, the world is your oyster… define success for yourself

I’ve learned through conversations and workshops with clients that success to many include: alignment with values, a deep sense of happiness in work, making a difference, freedom and choice, flexibility, confidence in running their business. There are many success markers that spin off these themes. But I think those capture the essence of values nicely. In the Life Proof Business Model, there is a chapter on SuccessScaping your life for those seeking connection between wishing for success and making the plan to get there.
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The Mistakes Success Entrepreneurs Make

Knowledge Collecting

Attending courses, going to conferences, signing up for free gift after free gift… knowledge is important, but success follows action. (shameless plug, I have just opened the doors… but am prelaunch so haven’t even announced it yet… this is why I have built my own “course” because I’m tired of hearing of people buying courses and getting no really value because they don’t know how to implement. My course is Life Proof Business Model — if you’d like to browse there is a link at the top of my website).

“Online Real Estate” Problems

There is only one place online that you completely control… your website (and if you like, to a degree your email marketing channels). Entrepreneurs easily get caught up in the costs of ‘pay to play’ and shrinking profile in audience’s feeds on Facebook, Twitter, Instagram, etc. In fact, several very popular “publishing” companies have shut down because they invested their entire business into being a “publisher” on the Facebook platform — they can no longer rely on the algorithm in Facebook to keep the volume of eyeballs on their content as they used to. The problem with this is, they never should have relied on that. They don’t own Facebook. Neither do you, neither do I.
Invest in the ‘pay to play’. Appreciate that social media channels are BORROWED or BOUGHT avenues. There are benefits. There are consequences.

Word Hoarding

Not investing in developing your story, your ideas, your help, your inspirations. Hoarding your thoughts and hoarding your words does not grow your business, nor serve your audience. What you know… what you do… it is a gift. If you don’t share you cannot receive back.

Evaluation Fail

How frequently should you evaluate your business methods? I would say daily. Successful entrepreneurs review, revisit, tweak and move on. Regularly. As regularly as needed. In fact, one of my clients is a Scrum trainer. The Scrum process is a contradiction to typical project management. It allows for ongoing experimentation and testing on weekly or biweekly basis. Avoiding frequent pauses to evaluate removes the opportunity to learn from mistakes and see what is not working, and what is.

Not Nimble

Being flexible to opportunities is critical, particularly in a digital age. The more things change, the more opportunities show up. I do NOT believe every opportunity is worthy of your business, however every opportunity should be considered against some criteria for your organization (values, goals, dreams).

Lack of Self-Care

This one is obvious. Yet not always so easy to attend to. In fact, many of us were conditioned to work, work, work. Self-care was sadly not really on my radar until my car accident 2.5 years ago… certainly not in a meaningful way, certainly not by choice (car accidents force it on you, but over these years recovery I’ve built new habits of self-care and am still learning). It is incredibly important to care for yourself in a way that helps sustain your mindset and physical being, or you will hit a wall (hopefully not as hard as a car crash) and your business will suffer. I feel very grateful that my business was 8 years old and I had built a solid, open, trusting relationship with clients and community. My business had major impacts (I stopped the launch of a major project and let clients go) but it was also sustainable because I had a business model that allowed me to scale down. That same model allows me to scale up. That same model allows me to sleep, go to physio, take days off, stretch, exercise, see therapists if required, meditate (oh heck, I don’t like meditating but this means hitting the mountains or ocean or listening to the birds or going for a drive with music loud and windows open).

Under/ Over Problem

No, not gambling. Undervaluing, over delivering: when we underprice or undervalue our own worth, our products, our services – we will resent our own business. No matter how much we love what we do and how appreciated we are…. When combining that with bending over backwards to serve and make customers happy also damages our brand. It hurts the perception of our worth. Both to ourselves and by others.

Under/ Under Problem

Underachieving, under delivering: do you not live up to your potential due to fear, lack of confidence, lack of clarity? We all cycle through this. The problem in underachieving and under delivering is you are selling yourself SO short of your potential. By underachieving, this is not necessarily in terms of time spent or quality of what you put out there, but rather, not pushing yourself to do the things you desperately want to do. Want to write, but aren’t writing? Want to podcast, but aren’t podcasting? Want to do Facebook lives, but aren’t doing them? These are examples of underachieving, under delivering. You have great things to offer! And these great things are the storytelling aspects of your business that makes you lose out on finding new customers in essentially the easiest way possible.

Comparison Traps

This is easily explained. I’m sure everyone falls into comparing ourselves to others at times. It starts when we being our journey doing market research. But growth comes from serving our customers in our own unique ways — knowing how to do what we do best in our own best ways — not from watching what others are doing. That is only useful to a point – but even then, it serves as distraction more than usefulness.

One Trick Show

Some businesses may be able to thrive on one sku, one product, one method of generating income… however, I believe to grow, thrive and survive the tough times (and we all have them) have 3 different sources of revenue at least is useful. This does not mean varying from the core of what you excel at – it means taking what you excel at and offering it in many different ways to suit your audience – in retail, you might bundle or offer seasonal sales or other. In services – we might offer individual support, group support, workshops.

Blind Trust

We don’t know what we don’t know. So at times, we may hand over the reigns of our business to others who say they do. There is HUGE risk in this. Particularly if you aren’t hands on learning what you don’t know. In my practice, I make sure my clients learn as I go along. There is less risk in not learning what I know, if you keep hiring a marketing pro or writer or brand strategist… because you will learn, by osmosis, enough to keep you rolling until you hire again. BUT, what about web development and all those systems and tools you need to link into. I CRINGE at how many times I’ve heard people say they have been LOCKED OUT of their website, their email service, even their accounting!  Blindly hiring an assistant or web developer to set up your accounts and use their own passwords and not share with you is an epic, painful, sometimes costly mistake. Whether you are a solopreneur or a CEO with a team, handing over your operations of any kind, without knowing how to get back in on your own is devastating. Handing over your money or spreadsheets or financial decisions to someone else can end your business if that person fails you. It happens. Don’t be naive.

Partner Paralysis

Collaborating is essential at times. I believe very much in sharing and collective thinking. BUT… it takes  a very carefully crafted arrangement to formally partner with someone. It goes beyond shared vision and trust. It goes deep into shared values and respect of real life stuff… real life really affects entrepreneurs. An ideal partner lets you roll with it and not feel burdened, left out or left behind. Legal requirements are essential. But personally, we can feel drained by partnerships more than bank accounts. I can think of many great partnerships… most are based on deep levels of friendship along with paired vision.

Race Not Pace

Living your business like it is a race, instead of a marathon is exhausting! You have to decide intentionally what pace you prescribe to. For me, I’m a huge advocate that slow and steady is okay. In fact, I’ve worked mostly part-time for 10 years on my full time business in a full time life. It’s not always part-time of course. There are cycles where it is an 80 hour work week — when I’m launching or working on an intense project. But usually, I pace slow and steady — if I didn’t, I wouldn’t be having a 10 year anniversary this year. My choice was out of necessity. I started a business with 3 daughters under the age of 5. And I’m still a mom too! It’s a priority for me. I only do work I can fully commit to so I have to pace myself with what I take on for them and for others.
Now, some might like to lean in or hustle. Good for you, if that’s the pace you feel works for you! You will reach goals faster, most likely. You may raise more money, quicker (not necessarily but it’s possible).
Either way it has to be sustainable!

Winging It

Throwing time and money and energy at every.random.idea is often a waste of time and money and energy! I deeply believe we all have a set of strengths we bring to our businesses at any point in time, and usually, when we honour what those are, we can start from our strengths and what we ACTUALLY know and avoid winging it. Playing to your strengths and then learning or hiring or asking to fill in the gaps of what you don’t know, is a more certain method of ‘winging it’. We cannot know what we don’t know, and mistakes will still happen! But ‘calculated’ winging it is a good risk that gives you information to work with and ‘instinctive decisions’ come from a framework of knowledge. Definitely take risks and try things, but if you are a business owner who feels like you are winging it chaotically and without a clue more than 20% of the time, I promise there is a better way. You need to build your chops, find a system that works for you and figure out your strengths (this is the entire structure of the Life Proof Business Model).

DIY Death

You aren’t an expert in everything! In some cases, you will learn, in other cases being a DIY business owner can kill your business. It certainly can limit your business. Because customers have an excellent sense of quality. And if your business doesn’t pass a “quality sniff test” because you’ve cobbled together aspects of your business you have no business touching, it makes you look less than the professional you are. The biggest area of risk is in DIYing the image stuff – your logo, your website, your brand identity, your copy if you aren’t a writer. I’m a fan of learning how to do nearly all aspects of your marketing as you can, to a point (when you are too busy, outsource – but watch the blind trust factor). But do NOT do your design or complex marketing tactics if you do not have trained skills. An excellent professional will ensure what is crafted for you looks and sounds like you…. this is BRAND strategy my friend and it is essential.

Image Over Inside Work

People who focus on ‘just’ making pretty things for their business or dressing the part or looking good are missing the essence of a quality business. And it takes time to get there. In fact, many people start with outside image first from a lack of knowing better or lack of knowing how to do better. I firmly believe in creating a professional brand, as stated above. Your ‘image’ is the window dressing on your brand and it matters. But, it is not the depth of your brand. It is not the heart and soul of your brand (although it definitely should reflect your heart and soul). The heart and soul of your brand comes from doing the inside work around your values, what you love, what you want to put out in the world, and how you want to deliver it. The heart and soul of your business comes from discovering your greatest confidence and projecting it with courage and clarity. This inside work is essential to developing and portraying the outside image. Three years into my business I rebranded my business from MPowered Marketing. While Truth & Tonic was an epic external image makeover, it was reflective of the inside work I did to discover my strengths and desires as a marketing professional. If it took me a few years to noodle over what I really wanted my image to represent, it is okay for you. But know that the outside pretty pictures alone are not enough to truly demonstrate your best stuff. You are your best stuff.

Money First

If success is defined by money. That’s fine. In fact, if you cannot truthfully say one measure of success is an income… then you likely aren’t being truthful with yourself. Conversely, at times when our focus is completely on money, it is easy to lose connection to what our customers really want and trust with them. Business is about building relationships and relationships don’t start by money-talk. Our job is deeply listen to customers and discover if we can solve their problems. If we do not listen and discover these problems, and focus on sell, sell, sell, we smell desperate and that is a huge turnoff. And it’s not who you are. Right?

Avoiding Mistakes

Don’t do it! Don’t avoid them. Make them fast, learn faster! In the Life Proof Business Model I have an entire module about evaluation mistakes you do make. But let’s really call a mistake what it is to a business owner… it’s a stepping stone from one decision to the next decision. Every single day we should make business decisions that are somewhat calculated risks, then step back and assess what part of that decision was great and what needs to be changed. Don’t avoid it. This is critical information to gather for making your next step!

My past 10 years of success looks like this:

I started this business when my daughters were 1, 3 and 5, which seems crazy now! Wow.
But with three little littles under foot (driving to preschool and kindergarten and changing diapers) while also being a very Type A go-getter, I had to set some strict definitions of success for myself. I could not ‘have it all, do it all’ without compromise to my family. While I fully support a parent who wants to work and have nanny’s or babysitter’s, that was not my choice. This choice was not always congruent with my passionate desire to be a superstar and international speaking career (that is still the long term goal)! So I had to (still have to) manage my mindset with other markers of success to suit my values in this phase of life.
So, my success equation had to be to grow at ‘slow and steady’ pace. I wanted to achieve my desired income while working part-time so I could also raise my kids full-time. I desperately wanted to break the mould on what marketing means to my clients (ew, marketing!) – if I can help them feel that marketing is fun, necessary, and doable, I’ve made a desired impact. That impact is success for me and my clients. And, after my car accident two years ago, I’ve embraced that my success really also includes self-care: a slower rollercoaster, more sleep, movement, and laughing at life and myself as much as possible.
So, what about you? What mistakes have you made that have made a difference in your path to success? What does success mean to you? I’d love to know!

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