How To Succeed As An Entrepreneur In 2020 — From Someone Who’s Failed Miserably.

When you read “failed miserably” in the title, what’s the first thing you thought of?

Did you think by failed I meant I haven’t made a certain amount of money?

Did you think by failed I meant I’m a workaholic with no life or family?

Did you think by failed I haven’t achieved XYZ level of success you deem satisfactory?

Did you think this meant I don’t have enough clients, or did you think this meant I haven’t spoken on stage… yet?

Please, take note of what your initial thoughts were because that will tell you what you need to do to succeed as an entrepreneur… and probably where you are failing.

Success is relative — we all know that.

Whether your vision of success is 7 streams of passive income with more real estate investments than you know what to do with…

Or being part of the who’s who of the influencer, personal development, or entertainment crowd…

Or just having more than enough consistent income to afford you a peaceful life away from it all, on a farm or in a cabin, where you can travel anytime you want…

Success is your vision and your version only. Everyone’s is different.

But, it’ll tell you a lot about where you think you’re failing when you see someone else describe their failures.

Failing To Succeed: How It All Began

I don’t think many entrepreneurs really understand what it takes to reach their specific, tangible measures of success.

When I started my coaching business in 2015, I had already been in online marketing for three years. I’d classify myself as entrepreneurial during that time, not an entrepreneur or business owner, although I was licensed.

To me, those first three years were a success. I was 21, had clear goals that were just a few steps ahead of where I was, I wasn’t attached to how they came, and I achieved them.

But after that… I got lost and felt stuck, which is why I became a certified coach. At the time, I wanted to use my natural adeptness to help people and, not to get too personal, I felt like it was a way to make up for a lot of my wrongs.

To feel good about myself. To ‘cleanse my soul’.

Little did I know the rampant journey of heartache and break, financial downfall, and setting myself up for failure as I had to face who I really was as a person.

Here’s the truth about entrepreneurship: it really is the fast-track to all of the personal development work and transformation you never knew you needed to begin with. It challenges every part of your mindset, your weaknesses, your insecurities, and your dis-abilities so that you can step into your role as a leader and a business owner.

So I failed miserably over, and over, and over… and over again. I’d take two steps forward, five steps back. I’d run full speed ahead towards my goals with anxiety and stress, or I’d burnout completely and lose momentum. I’d go after other people’s goals (which is why I’d never achieve them), use strategies that weren’t a good fit for me (which is why I’d fail at filling my pipeline or growing my audience), and push my back against the wall constantly (which is why I faced eviction and car repossession) in order to break these debilitating habits that don’t allow you as an entrepreneur to succeed.

Success Takes Time

The first thing I misunderstood about success was that it takes time. It just does! Success is growth… do we grow from a five year old’s body into a fifteen year old’s overnight? No! And thank God, if you’re anything like me the growing pains I had were bad enough!

I see a lot of thought leaders and mentors for entrepreneurs share content under the premise that “patience is underrated” and “you don’t have to wait for success”, and in some instances this is true. But I think this sets a lot of entrepreneurs up for failure because they’re expecting that they can just take a few steps toward their goal and boom, magically clients or sales will appear.

Considering how fast the landscape of online marketing is changing, how overcrowded all (yes I said all) industries are, and the constant upswing of people starting businesses, I think it’s pretty safe to say the amount of time and consistency required to truly grow your business is only going to get bigger.

That’s not to say you can’t start seeing results towards your goals now, and I do believe in measuring small measures of success daily or at least weekly to show yourself your progress. It’s also been my experience and countless others that if you do want to ‘shorten’ the time period between goals, the more “big” (relatively speaking) steps of action you take, the faster the results.

Big Action Takes A Big Mindset

Something that, for years, I didn’t have. I say years not because I’m mentally where I’d like to be as a business owner (Grant Cardone anyone?), but I’m miles and miles ahead of where I once was.

I think that mindset starts with recognizing you are not a failure… at all. Leveraging your failures is what it really takes to succeed as an entrepreneur, and you can’t do that if, in your mind, you are constantly failing and looking at your mistakes as a result.

I was completely incapable of taking ‘big action’ when I first started. A large part of that was I wasn’t clear on my target. In my formative years, when I wanted something, I just moved full speed ahead to get it. I didn’t need to be super specific or methodical about it. I took that same mentality towards my business and, well, it didn’t get me very far. As I mentioned earlier as well, I leeched on to many of the versions of success other entrepreneurs have.

The path to success is clear when you truly want it… which I did not. I didn’t know what I wanted. I never envisioned myself as an entrepreneur until then, or a coach, or having an online business. I struggled to create my own personal goals because, if it wasn’t clear from earlier, I had started this business for the wrong reasons. I was “running from my past” and I wasn’t giving myself permission.

Although this past year, 2019, was filled with many, many challenges, it was my best year yet as a business owner. Why? I took much bigger steps of action than I ever had before. I did what I needed to do to push pass my insecurities and small mindedness, took risks going after much larger clients, stuck my neck out there, raised my prices, changed my positioning, and had a few leaps of faith when deep down inside all I could think was, “I have no idea what the hell I’m doing.”

I guess you could say I reached a new level of #adulting in my business.

That Mindset Will Come At A Cost

It is true what they say that no one else is going to understand your desire for success but you. Everything in your reality will try to distract you from your vision, your goals, and the action you should (and want to) take. I didn’t really understand this until I started taking an observational seat at my own behavior.

When you really start to shape your reality from the mindset of a leader, all of your habits, self-awarenesses, beliefs, and ways of living will smack you in the face so you will continue to decide, “do I really want this?”.

You have to really want it.

When I started my business, I had a serious case of the ‘shoulds’. I should show up online consistently, I should learn how to do this, I should be cold emailing higher level prospects, I should be… etcetera. I don’t know if you’re like me, but I don’t like being told what I ‘should’ do. I’m a rebellious, independent, only child not here to people please, and that includes myself. So having this narrative really destroyed me for a long time because I told myself I ‘should’ be doing things that (get this) I actually wanted to be doing.

But the mere fact that it felt like a ‘should’, or like a burden to me, made me run into a boatload of walls led by my friends procrastination and excuses.

Speaking of people pleasing, those around will think you are crazy. They’ll think you’re a workaholic. They’ll tell you it’s okay to take a break. They won’t understand why you’re working so hard with ‘little results’. They’ll sound supportive, but you’ll have to make sure you receive that support for yourself. You can’t try to fit in, and you have to choose your passion over your comfort.

Let me just preface that I don’t believe succeeding as an entrepreneur has to be hard work. When you are driven by passion and purpose (as cliche as it sounds), it feels good. And when it feels good, you’ll do it. When you do it, you reach goals. When you reach goals, you succeed. Boom. Piece of cake. Right?

Not for me. The whole “have a business doing what you love!”, even when I started “doing what I love” wasn’t something I could resonate with.

I had spent a large chunk of my life at that point running away from my passions and feeling like I had no sense of purpose. I carried a boatload of fears, beliefs, patterns, and behaviors with me that caused me to have a difficult time coming back to that point of passion and deep care. It wasn’t until I let myself connect to that again, fully, that success started to flow naturally (success to me being defined by opportunities to do the work I love, with clients that are ideal to a ‘T’, while reaching sales goals, and having my life outside of ‘work’ be just as fulfilling).

Failing Miserably Is An Art

Truly. If you feel like you’re failing as an entrepreneur, take a step back and observe your behavior. What have you been doing consistently that causes you to feel like a failure? What do you see as a success, versus a failure, and what’s the difference between the two? When you remove yourself from your actions, you can see patterns and a lifestyle that supports your mindset and artistry.

It’s not easy to fail, truly! It takes a lot of dedication, hard work, focus… borderline obsession.

You don’t have to fail miserably, however, especially when you are able to look at the positive outcomes from points of failure and use that to catapult your growth. If you’re going to continue down the path of entrepreneurship (or life in general), you’re going to fail. Don’t make a big deal. My success tips for turning those failures into opportunity, profit, and fulfillment?

  1. Give yourself permission. Permission to succeed, permission to fail publicly, permission to share your unapologetic opinions, to take risks and listen to yourself, not the gurus… Give yourself permission for whatever it is you are craving or feeling pulled towards along your entrepreneurial journey. This is the only way you are going to open yourself up to what your truly believe is your version of success. This is probably the biggest feat to overcome for (new) entrepreneurs because we’ve grown up, in all societies and cultures, to believe we need to be told what to do. That there is someone greater, bigger, and smarter above us that we need to listen to instead of listening to ourselves.

We also punish ourselves for more than we’d like to admit. Wonder why you’ve had the idea to write that personal blog post for years, but haven’t? Want to know why you have all the tools you need to get on national TV, but haven’t put yourself out there? Know that your funnel works great, but you’re still not closing deals? Self-sabotage/punishment is probably the culprit. Do what you need to do to forgive, let go, and give yourself permission daily to get your goals accomplished.

2. Take risks. Along the same lines of giving yourself permission, you have to start taking risks. It will probably start as bite sized risks here and there, and grow into larger leaps, but start somewhere. My philosophy that’s worked pretty well: do something each day that scares me or makes me feel extremely uncomfortable. If I don’t, I can clearly recognize that I was avoiding taking steps of action I know will help me achieve my goals. Maybe I was tired that day, maybe I had a ‘win’ yesterday so I think I can take my foot off the gas… nope. Don’t let anything get in the way, because trust me, your back will soon again be against the wall. And you will fail.

If you are a business owner, you are a leader. Leaders have to take risks and lead, even if that means making a mistake or a fool out of yourself. Not fully convinced? Think about this — millennials and Gen Z’ers now have all the buying power. They care more than anything else about purchasing from brands that are authentic, real, and they can build an honest connection with. What does that mean? That means it’s safe to make mistakes and not look perfect in front of your audience. In fact, it might make you more sales than you had planned on.

3. Above all else, believe in yourself. Sure, you may have had a long day and just want to curl into a ball and watch Billions. Or Marvelous Mrs. Maisel. Or Disney Plus. (I have more than a few favorites…). But what’s more important? Believing in your dreams and holding on to that passionate purpose? Or believing in comfort because watching TV is self-soothing. Don’t get me wrong, I think self-care (entrepreneur or not) is of extreme importance. I don’t believe working day and night on your business will help you succeed faster (trust me, I’ve tried it).

When you have full belief in yourself, those thoughts that make you want to step away from your passion, or the people around you who, mean well, but tug at you to step into their world? You can easily say no to them. Believe that you can and you will achieve your next goals, regardless of how long it takes or how you get there. Know your limits, yes, but also know that staying tapped in to this will fuel your energy more and bring you success faster.

4. Trust your gut. Especially if you are crystal clear on where you’re headed, your intuition is your best, secret weapon. I can’t tell you how many times I’ve listened to the do’s and don’ts of online marketing, or stuck with my strategy because it appeared to be the right thing to do, only for it to blow up in my face. Thankfully, after one too many of these occasions, I listen to my intuition no matter how risky, unrelated, or illogical it is. It always, always leads me in the right direction because it is driven by my passion and my purpose, not by logic.

Well, who’s ready to fail their way into success in 2020!?

I know one thing’s for sure, the entrepreneur/startup world is moving faster and faster. You don’t have time (or room) to get lost in other people’s opinions. Do what’s right for you and give yourself permission to have a clear vision. The more you practice the consistent art of failing and learning to leverage it for growth, you’ll see your seeds of efforts sprouting and be gifted opportunities that you couldn’t see coming yourself.

What was your biggest failure of 2019, and how did it lead you into success? I’d love it if you would share with us below.

Human-centric, data-driven Marketing Director @ FreeByrd. Writing about tech, startups and B2B marketing. Fueled by coffee and dark chocolate.

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