Drafting this post on my Copa Airlines flight from Panama City --> Mexico City on 28 December 2015

Drafting this post on my Copa Airlines flight from Panama City --> Mexico City on 28 December 2015


My 2015

The media and millennials make entrepreneurship seem glamourous. In many ways compared to the confines of corporate, government, or non-profit work, charting one’s own destiny appears incredibly enticing and liberating. However, the part that seldom is talked about outside of entrepreneurial and startup circles is just how brutal this path can be. On a flight between Panama City and Mexico City, I reflected on my second full year of living the entrepreneurial experience. My hope is that these lessons (in no particular order) are useful to you whatever your profession or path may be. 


1 - Be Fully Present - I am most effective when I do one thing at a time

Maybe its because I’m a dude that I can’t multi-task worth a damn. For example, if I try to read an email while on the phone I tend to tune out the conversation. Or if I am toggling between apps on my iPhone I seem to never advance any particular thing I attempt. I’ve learned that the way I get the most done in a given day is to tackle each thing with singular focus. It is contrary to the methods of many people I know who claim to be multitasking mavens. Perhaps it works for them, but I doubt it. If I just sit down and bust out a given task it takes only a fraction of the time than it does if I do it in the midst of many other things. In conversation, which is a critical component of what I get paid to do, multitasking also exists when I am not being fully present. If in my head I am having a conversation with myself (where will I have dinner? does he love me? did I send that invoice?) I am also multitasking. Thankfully my daily meditation practice has given me significant facility to be fully present in my conversations, which makes me much more effective in giving business advice because I can actively listen.  


2 - Delivery Drives Growth - Focus on providing value to current clients to create new ones

After signing a contract or renewal I am tempted to think “okay, what’s next?” in regards to my sales pipeline. I think it's due to that uncertain entrepreneurial feeling of never quite knowing where your future revenues will come from (or even if they will come at all). What I’ve learned is that my next sale is actually this one. Delivering on what I committed to, and ideally more, is the best way I can establish a professional reputation and brand based on results. I’ve found that executing what I have under contract in a way that fully satisfies my clients is the best way to generate future business because they become my extended sales force, amplifying my message. A great deal of my business growth in 2015 came through referrals from existing clients. There is no higher compliment, or potent sales method, than existing clients who suggest me to their friends and family. Thank you to my many clients who have entrusted me with such introductions. 


3 - Keep It Simple - Complexity is the enemy of progress and success

One of the downsides of my creativity is that I come up with a mountain of ideas that get me very excited. As I develop a plan it can quickly become a science project, fraught with complexity, dependencies, flying in the face of the law of diminishing returns. This manifests as projects crawling along from concept to reality, at high cost, with a great deal of effort for me and my team, that can be more effort than they are worth. My training as a lean six sigma black belt taught me that complexity decreases quality and increases cost and timelines. I’m paying extra attention to what is critical and necessary now to get something done vs. what is nice to have. What I’m seeing is the vast majority of what turns my crank personally is not needed to complete the task. Less complex work scope means less cost, higher quality, and faster delivery. 


4 - The Importance of Vulnerability in Business - Showing my faults makes me more credible, not less

Perhaps it's lingering feelings of inadequacy or pressure from social media and other sources that led me to feel I needed to appear very buttoned up. After all, I’m in the business of giving advice and supporting smart decisions, so I best be doing the same in my own business and life, right? I felt tremendous pressure to paint a compelling picture of my progress and success. I always did this in an authentic way, but it was highly edited, omitting the many mistakes, failures, low points, and other moments of feeling low. How could I share these and be credible as a business coach? After reading Daring Greatly exactly a year ago I realized I had it all wrong. Mustering the courage to share my vulnerabilities, including my missteps, negative emotions, and fears, was exactly the thing that would bring me closer to people and make me more relatable. I still have an impulse to only share the “good stuff” but instead make a concerted effort to share my whole self and have found the real “good stuff” is actually the relatable ordinary aspects of the experience of being human. 


5 - Cash Is Life - Nothing stresses me out more than not having enough money to operate

Being a committed “upside” guy my general focus is on revenue generation, not expense management. Any weenie with a spreadsheet can control expenses. It takes much more to actually go out and convince customers to part with their money in exchange for my services. In 2015 I did a great job of generating revenue (and surpassed my stretch goal). However, in Q2 I did a poor job of managing my receivables (money I earned but had not been paid to my company). I was so heads-down delivering services I neglected to be “on it” with making sure I actually invoiced for the work I delivered. Thus expenses, which burn at a pretty consistent monthly rate, stacked up and my cash on hand to pay them quickly depleted. I ended up very stressed and racked up some significant, but temporary, corporate credit card debt for a few months. Lesson learned. I now have a system that reminds me when to invoice and when to follow up. 


6 - Get to Ready - Organized systems and spaces keep me sane and make me feel powerful

While my brain is organized like a bento box, some of my physical spaces and processes, better resemble a basement or attic. Cluttered, dusty, overwhelming, and anxiety producing. In 2014 I made getting more organized a key area of development. A critical component is moving away from relying on ineffective and ancient relics like email, digital file folders, and documents as a method of organization. Becoming an avid Evernote (my brain in the cloud) and Asana (my virtual organizer and nag) user, along with religiously using my Sunrise calendar and properly setting up QuickBooks with the help of my book keeper, were key improvements. I took things to the next level when I hired a Certified Professional Organizer who conducted an exhaustive audit of my business and personal life (down to my underwear drawer, people!). What resulted was a giant plan of one-time purges and more importantly new systems to maintain tidiness and order. Implementing this plan, along with a series of coaching conversations, infected me with a mindset about how to create and sustain sanity through organization. To me, “getting to ready” means structuring everything I do in life, professionally and personally, in a way that is easy and leaves me present and feeling powerful to pursue my dreams.


7 - Be Visible - Being on the radar of others requires consistency and yields great surprises

In my volunteer work in Washington D.C. a successful lobbyist once told me “it's not who you know, it's who knows you.” Amen. While most networking wisdom and content focuses on one's “rolodex” I’ve found its far more important to be listed in those of others. There are endless conversations, meetings, thoughts, etc. that I will never be at the table for. What I’ve realized is most important is being on the mind of many diverse people, in particular ones that I wouldn’t expect to want to engage me. Others having me, and a loose understanding of what I do, in their ambient awareness has generated significant revenue for me in 2015. I have gotten numerous texts, Facebook messages, emails, LinkedIn notes, calls, and even Instagram comments that have converted to new deals. Most of these have been a complete surprise to me, including a number of then strangers being aware of me but me not having been aware of them. Thankfully social media and other tools have made it easier than ever for me to have a micro presence in the minds of many people. Another component is just being open and ready for opportunity including always having business cards on me (even when taking out the trash), and answering calls from a unknown numbers. I just assume its someone calling to do business with me!


8 - Cast a Wide Net - Never bet my pipeline on an opportunity; always diversify my business development

A mistake I made early on with my business was getting punch drunk on a potential client prospect. I would submit a proposal and then coast, assuming the business would convert. What I’ve found is that it is very hard to predict which prospects will covert to paying clients and which will not. People get busy, they change their minds, they don’t have the money, they get confronted, they don’t click with me, they find someone better, they don’t end up buying from anyone, etc. In my early 20’s a friend in sales told me the phrase “Some Will. Some Wait. Some Won’t. So What? NEXT!” In short, regardless of what customers do or don’t do, keep going. I have matured to no longer mentally cash a check when I submit a proposal, and I assume it has no better than 50/50 odds of success. I pursue other opportunities in tandem. I realize the limitations to predict prospect’s behavior and as such ensure my pipeline is filled with multiple opportunities. My proposals typically are only valid for one week and I can always say no (which I have done multiple times) if I have too much on my plate. 


9 - General Management Trumps Vision - The unsexy grunt of effective supervision of people and work is really the magic

Media is packed with articles and content on innovation, creativity, strategy, and other sexy components of business. I’m into all of that but in reality ideas are abundant. The ability to execute on ideas is far less common. Being a superb general manager of people, work and processes, is far less sexy yet far more impactful. I’ve seen results snowball from components as fundamental as: ensuring effective communication and understanding between parties, setting clearly defined expectations for work, being decisive, providing direct and timely feedback, establishing budgets and timelines, fielding A-player talent, and leveraging outside expertise and resources when necessary. All of these things are about establishing a general sense of rigor in business that makes getting work done an efficient, satisfying, clear and effective process. I focus the vast majority of my time on general management vs. strategy or innovation. 


10 - Fiercely Protect My Time - Nothing is more important to leverage and protect than my calendar

My dad always said “your time is your most precious resource” but it sure didn’t seem so in my youth. Now I realize just how right he was. It is easy to be a slave to my inbox, other people's requests, and highly inefficient ways of working. One of the only fair things in this world is that we are all given 24 hours every day. To a certain extent I can buy time by paying others to do things that would otherwise occupy my time, but there is a low ceiling here. So I’ve had to be much smarter about who I agree to meet with, how I triage email communication, what I get involved in, and how I structure my day. A key component of this is trust because I both have to trust in my judgement that I am making the right decisions, and trust my team and providers with the vast amount of things I delegate. I’ve also developed the ability to quickly recognize when people are wasting my time and guard my time more closely that I do my money. 


11 - Take Care of Myself - Investing in myself, including self-care, is my highest ROI opportunity

While I leverage a myriad of talented providers and staff to help me be successful, the responsibility for my results is 100% mine. I’ve frequently found myself in a hole of exhaustion, overwhelm, fatigue and fear, and just kept digging. I’ve foolishly thought I just needed to work more, power through it, or even buckled to a feeling like I didn’t deserve to take care of my needs. Now I realize that if I don’t take care of myself I can’t be very effective with my clients or my team. In addition, I now see that every dollar and minute I invest in myself has an incredibly high return on investment (ROI) as I accrue 100% of the benefit, and it compounds over time. There are a variety of ways I have found to take care of myself. Meditating (Every. Single. Morning.) for 23 minutes is one of them. Or seeing my therapist weekly. Or exercising frequently. Or paying for things to get done on my behalf to free up more of my time. Or saying no and setting boundaries. In doing so I not only ensure I am taking care of my needs, I better position myself to take care of the needs of my clients, team, and loved ones because I am stronger, wiser, and healthier. 


In Conclusion

Thank you to my clients for giving me a shot, to my team and providers for supporting me, and to my broader community for encouraging me. 

May your 2016 be one of boldness, focus, grit, and triumph.