The Leap: How do I know I am ready?

Happy Sunday! You know what that means? It's SUNDAY FUNDAY and we are talking all things small #biz + taking the leap. Making the transition into full-time entrepreneurship is scary! It is intimidating to look out into the ocean of unknown and actually jump. One of the questions so commonly asked is "How do I know I'm ready?" Well, today I am excited to have Wes here with his top tips for prepping yourself for success.

The following is a guest post by Wes Lehman of Urban Buffalo Marketing.

Wes is CEO and founder of Urban Buffalo Marketing based out of Tampa, Fl. Passionate about helping businesses grow and succeed online, Wes is an advocate for digital strategy and success. For more information, visit or contact Wes at

I always felt that I was different.

I was never a perfectionist, but I was never satisfied with the status quo. I always saw things as they were and imagined how much better they could be. I was constantly seeking approval for my work, yet I was uncomfortable being overseen. To be honest, I was confused about who I was and who I was supposed to be.

    Growing up working on a farm and working as a contractor in many different fields, I took pride in the fact that I never had a real boss. While in college I eventually grew into a pattern of working regularly with a single company and began to put in full-time hours with them. The pay was good, the atmosphere was relaxed, and the people in the company were phenomenal. One night after the CEO treated us to a night of seafood and drinks. I remember saying, Theres no company that I would rather work for.

    Fast forward two months. I felt like I was suffocating. I dreaded working every day. It wasnt the company, it wasnt the pay, it was me. So I decided to take a leap. The kind of leap that I know youve thought about because, lets be real, why else would you still be reading this?

    That leap is one of the greatest choices I ever made. In one week I made more than I had in an entire month at my previous job. But heres the catchthis was only 4 months ago. My entrepreneurial expertiseprobably doesnt line up with most articles youll read, heck it may even be less that yours, but I do know that it is RAW. It is raw because I am living it right now, not reflecting on it 20 years later.

    I am pumped to be able to share 5 of the most important things Ive learned taking the big leap. I promise to make this as practical and applicable as possible; no fluff.

Patience - The Thing I Did Not Have

    “Wow, ‘patience’? Really? What a fluffy start”. I know, I know. But give me a chance here. Chances are, you’re probably dying to get started with your entrepreneurial journey, but jumping in right away isn’t always the best start. Take a moment to step back. Think about your life balance. Is there a way you can make a smoother transition than cutting cold-turkey and starting anew? One option is to start your business as a “side-hustle”. If you work 9-5, Monday - Friday, set aside a half-day on Saturday and maybe an hour before/after work that you can dedicate to your new adventure. This way you don’t have make the big jump without having some sort of serious ground work already in place to ease that transition. This will also allow you time to study and plan for your full launch-mode.

Which brings us to…

Planning - The Thing That I Thought I Had Done Well

    Part of my story that I didnt tell you is that I actually intended to launch my business a year earlier than I did. I pushed back the date until I felt like I was going to, well, suffocate. However, now, I am incredibly thankful for this time that I had because I was simply not ready, I just didnt know it at the time. I spent almost all my spare time throughout that year studying the industry, watching trends, writing out business plans, re-writing out business plans, and re-re-writing out business plans. It was a never ending cycle. When it finally came time to launch, I felt very prepared.

    Well, it turns out that I was NOT prepared. Two weeks in I almost completely reworked my strategy and my business model. Why? Because I Planned, but I did not Practice.

Practice - Makes Perfect(ish)

    I tend to be an all or nothingtype of person. At times though, that plays to my disadvantage. Just as the eye is bigger than the stomach, my ambition was bigger than my practicality. I launched my digital marketing company because digital marketing is my passion, not because it was a field that I was in before.

    So what does this look like practically? A big part of what my company does is website design. Well, the very first website that my company had ever designed wasour own. The second one was our clients. In all honesty, we were not experienced because we never practiced in the real world. We never ran it as a side-hustle, we never ran test trials, and at first, we put out a product that we were not satisfied with.

    It is important that as you prepare to take the leap, whether as a company or as a solo-preneur, to have played in the space you will be operating in. Even if you already have the head knowledge like we did, putting that knowledge into action is a whole different game.

Pricing - The Struggle Is Real

    This isnt a struggle just for entrepreneurs, its a universal struggle for businesses across every industry. A lot of people ask, Where do I start? Am I overcharging? Am I undercharging?. Well, 9 times out of 10 you are probably undercharging. After youve finished the first 3 Ps (Patience, Planning, Practice) ask yourself this:

    What is a realistic financial goal for me in the next 12 months?

    From there just do the math and price accordingly. Youd be surprised how much people are willing to pay, especially for services. If you still feel uncomfortable with that figure because of a lack of experience, work your first client for free. Tell them you are trying to build your portfolio. Then do your next client for 50% and the next one full priced. I promise, youll feel comfortable being paid in full. Its a nice feeling.

    If you’re anything like me, being an entrepreneur means doing something you are passionate about. Which can often turn into doing things for cheap or free, dont fall into that trap for very long.

Perseverance - C’mon Man, More Fluff?

    Okay yes this “P” is a little more general. But I cannot emphasize enough how important it is. Keep moving forward. You will have burdens that seriously weigh you down. I’m not talking about bumps and hurdles in the road (though there will be plenty of those too), I’m talking about the things that will eat away at you and make you think that there is just no way to keep going. This is different for everybody. It may be trying to keep your family financially afloat, it may be your family and friends not supporting and encouraging you, it may be your health, or a myriad of other struggles. 

    I feel like I’ve already talked about my experiences too much, but hey, it’s all I really know, right? I suffer from—no, I deal with—chronic pain and weakness in my joints and muscles every day. Lightly put, it sucks. On a good day I spend an hour stretching and a good bit of time laying down. On a bad day I have to stretch for 2.5 hours and spend many hours lying down. But we were all given burdens to carry. This is just mine. Yours is probably different and you probably handle yours better than I would.

    Just know this, if you let the struggles and burdens weigh you down so much that you never take that leap, you will never know how much you might have missed out on. I’m not trying to give you some motivational BS. I’m just being real. Taking that leap was the greatest decision I have ever made. I just want to help other people get there too.

So, what about you? Are you ready to take the leap? Are you scared? Let me know below!

Ashley McAlpin4 Comments