Where do you want to go? Where are you now? Are you getting to where you want to go?
These are questions I’ve been fielding recently. However, these are questions that should be periodically asked and answered. More than likely, myself and many others ask these questions only when things are bad. That is, thoughts arise like, “I don’t like where I am, what should I do next?” It’s akin to reevaluating bad habits or poor exercise form only when pain occurs. Even less often is when longer-term questions are asked.
It’s a problem.
We shouldn’t ask these questions so rarely. We definitely shouldn’t ask these questions simply when things are not going well. (“Don’t go to the grocery store when hungry” comes to mind.)
We should ask ourselves several times a year where do we want to go. Has this changed since the last time we asked? Why?
The difficult part of not asking these questions periodically, then, comes when we have to ask the question not out of a want and simply to stay aligned. Instead, the difficulty comes when the change must come out of necessity – when a drastic change must occur. The difficulty comes when we find ourselves further beyond our locus of control. The difficulty comes when things have become easy or comfortable, and we’ve adopted a higher luxury. That’s when lethargy comes in and we forget about our why.
Ask yourself: Where do I want to go? Where am I now? Am I getting to where I want to go? If not, how do I get back on-track?

John Greathouse wrote back in May about practicing entrepreneurship with a purpose. John talks about deliberate actions before (or during) diving into entrepreneurship.
It’s a great reminder-type post as to what drives many entrepreneurs beyond building a company and, yes, the chance at making a substantial lifestyle change. For many – me being one of them – there’s a drive and passion about the challenge and impact of building something great from nothing.
A few points John shared that I strive to practice everyday:
  • “Advise A Startup”. I love speaking to startups, entrepreneurs, and wantrepreneurs. Networking is great, but hearing the problems others are solving and how is highly educational. As John also said, teaching others is a great way to amplify and accelerate learning.
  • “Don’t Throw Up, Speak Up”. I grew up as an introvert, but realizing what I wanted to achieve, I wanted to be more extroverted. So, I hacked my personality for years and got comfortable doing uncomfortable things (i.e. giving presentations as often as possible, meeting others by simply starting with “hi”, etc. It starts with deliberate, small actions. Overtime, it gets easier – not totally comfortable, but you develop a strength to be successful at it.
  • “Entrepreneur It”. Entrepreneurship really builds on my past life as a consultant (looking for problems, finding solutions, and implementing solutions). I do this often in everyday life including random interviews of flight attendants during flights or door-to-door surveys at local restaurants. There are problems everywhere, and you can exercise that creative, problem-solving muscle everywhere, too.

Find ways to practice entrepreneurship with a purpose. Take small, deliberate actions consistently. You’ll be amazed how opportunities start to flow. Then, take the leap.

I recently met an author of several books and also had a startup some years before. She lamented how her beauty product was probably too early – timing, indeed, is an important factor in startups. She also shared how many of her books failed to be commercial successes.
Knowing what my own book was about, she asked me, “When did you know it was time to stop?”
I get asked this a lot. Perhaps everyone believes an author on startup failure knows the moment. Perhaps I know the signals, the omens of impending startup doom. That, sadly, is not true at all. It’s not true because there’s no answer. It’s up to the entrepreneur(s).
Steve Blank used a comparison in “Venture Capital is ‘Liquidity Ponzi Scheme” that I often use: “entrepreneurs are like artists”. Both can accomplish great things and be wildly successful. Both can be wildly misunderstood, too. Both, likely, must overcome the roller coaster of ups and [many more] downs before finding success (if ever).
Entrepreneurs and artists are driven by a mission and passion. That’s what keeps entrepreneurs and artists going.
Entrepreneurs, like artists, see the world in their own ways (“different”). Often, they misunderstand or meet odds and antagonists all over. To entrepreneurs and artists, the challenges are opportunities.
When I looked at the author, I responded, “you stop when you’ve lost the passion” referencing what happened at Body Boss. We had lost the passion to keep hitting and overcoming challenges.
A Google search of “failure” and entrepreneurs returns thousands of results, and indeed, entrepreneurs. Jack Ma, founder of China’s Alibaba, is one such example of extreme grit and persistence – his failures are well-documented. When entrepreneurs ask, “when do we know when to quit?”, they are looking for reasons to quit. Many are looking for outside influences to signal to stop when the true answer lies within.
You’re going to run into challenges (opportunities) as an entrepreneur or an artist, no doubt. What will keep you going is passion and a belief in your mission.
Took a hike on Saturday morning to the top of Stone Mountain to catch the sunrise. There are a million reasons not get up this early, but if I hadn’t, I wouldn’t have caught this beauty.
If you’re a mountain biker, you know the importance of picking a line, attacking it, and driving your legs to get through tricky terrain. Turns out, this line-attack-drive mentality is actually pretty applicable in the world of startups and entrepreneurship, too, but not just in navigating the treacherous terrain of entrepreneurship, but also in just starting out.
When I was younger, my buddy and I biked around the neighborhood looking for “mini-off-road adventures”. That meant going down stairs around the ‘hood, flying through the wooded backyards of neighbors, and occasionally, fording a creek bed near the neighborhood pool.
The creek had rocks and dips in addition to the slow current of the creek, so it made for a “risky” adventure – hey, we’re in the suburbs. The key to navigating the traps and obstacles was to find a line, attack it, and keep churning your legs.
At first, my buddy had trouble fording the creek either stopping well before entering the creek or right smack in the middle. But once he focused on a clean line free of rocks and big dips, finding momentum into the line, and then driving his legs, he was crossing the creek almost effortlessly.
I’ve recently sat down with several “wantrepreneurs” and musicians, and so many of them are stuck in this “I’m not ready” phase or “I’m waiting for… [insert ‘stars to align’ here]”. But as they’re waiting for the right people to come aboard to help or for themselves to have the confidence to try, years have passed by. And in most cases, those ideas are now yesterday’s someone else’s successes.
So why are people holding back? How do you just “pick a line, attack it, and keep your legs driving”? Everything’s easier said than done, but maybe being conscious of what’s holding you back is a step towards accomplishing the goals you’ve set forth for yourself. So here are a few thoughts:

Surprise! You’re afraid of what others think.

How many times are we afraid that others won’t like what we’re doing, or they “disapprove”? Funny thing is that everyone has their own priorities, and you should too. That priority? Yourself.

I happened to meet a young girl in high school who said she liked to sing, but she didn’t consider herself a singer or musician. In fact, when my friend and I asked her why she didn’t share her music more, she mentioned “mean girls” at her school. Wow. That was truly sad. She was holding herself back from her passion, afraid of being teased by others who really didn’t care for her. Meanwhile, those who did care for her encouraged her, but it was the rotten apples in the group with nothing positive to say who held her back.

What you’ll learn in any marketing exercise, especially in startups, is that you’ll have multiple levels of the market, and those who your message resonates with are the ones who matter the most. It’s that depiction of a funnel where the right audience who comes through at the end. And believe me that there are plenty of people who will care about what you do and say.

You think you’re not ready.

“If we wait until we’re ready, we’ll be waiting for the rest of our lives.” – Lemony Snicket

Truth is, I don’t think we’re ever truly ready for a lot of things. Couple examples:
  • I hear from my friends who are now parents of little ones that they didn’t think they were fully ready, and even when their kids were born, they weren’t. But they learn on-the-fly.
  • As I’ve started consulting independently, I’ve had to rely a lot on my own experience and skills and my ability to quickly learn. Once I sold myself on projects and started working on them, I’ve continued learning which has been my way of powering through (the drive). Sometimes, it’s smooth, sometimes it’s not. But each time has been a great learning experience.

When we pursue a dream or a passion like entrepreneurship, we have to be strong, smart, and vulnerable enough to ask for help. Those capabilities you think you may lack can be learned, and asking for help is one of the best ways to do that.

It’s amazing what happens when we actually push ourselves and keep our legs churning – we accomplish what we didn’t think we could.

With more time (and falls), you seek the path of least resistance.

I was hiking on Stone Mountain this weekend, when I realized I started picking lines on the trail with the smallest “steps”. I remember I used to love jumping down the larger boulders. Now, I’m nursing a sprained ankle (I’m like Mr. Glass these days), and I’m consciously more cautious of what line I take.
When I was younger, I would dream about mountain biking up and down this granite. Now? Now I’m slowly, cautiously stepping down each boulder. Ah, how the years have affected my risk aversion…
As we all get older, “wiser”, we’ve got more experience and scars that keep us from both getting hurt and attempting anything too risky (like a growing family). Sure that can be a good thing, but it can also hold us back as we settle into a pattern. It’s important to weigh risks against the opportunities and realize, too, that some risks aren’t really risks at all. Instead, they’re just excuses.

You don’t think you’re good enough.

Patrick McKenzie (of Kalzumeus Software) wrote a post about the need for salary transparency in Talking About Money, but he also shared a little nugget of truth about skill growth. Patrick increased his consultancy rates dramatically from $12K per week to $30K to $50K (PER WEEK!!) DESPITE his skill levels being largely the same. Instead, it was his ability to continue to market and sell himself that drove up rates.
When we’re afraid to venture out on our own or to share our music or our ideas, most of the time, it’s because we THINK we’re not “good enough”. However, in most cases, we are. Patrick continued growing his consultancy rates by learning and iterating over the years. It took practice to learn and iterations… practice and iterations he would never have if he never started.

You put others and others’ obligations ahead of yourself and your own.

I was talking to my musician friend the other day. I’ve heard his stuff, and he’s genuinely a great musician, but due to his work with others, he hasn’t put out any new music in years. At least, he hasn’t shared it. It makes me sad a bit.
I explained it to him like his personality… he’s a great guy, has a good heart, and has some deep, creative thoughts. However, most people don’t know him that way because either he doesn’t open up to others or strangers don’t just say hello. I just happened to be the Curious George to say hello.
His music, like his personality, will never be liked, disliked, or even known it ever existed if he doesn’t share it with the world.
It’s easy to be so focused on the day-to-day that our true passions fall to the wayside while we earn the paycheck that puts food on the table. Important, sure. However, perhaps it just takes being conscious of the lack of effort we spend on what we’re truly passionate about to seize the opportunity and share.

The most successful DO-ERs know that stagnation is a trap, and it’s got this gravitational pull that keeps us there. They know that the only way to success is to… well, DO. Pick your line (your direction), attack it (you do), and drive through it (learn, iterate, keep doing). 
How would you use the Line-Attack-Drive mentality to achieve some goal you’ve set? What other step do you think is missing from this?
Source: http://www.quotesvalley.com/images/09/motivation-is-what-gets-you-started-habit-is-what-keeps-you-going.jpg
Recently, I got a chance to sit down with the President and co-founder of IRUNURUN, Travis Dommert. Met him walking down the street of Piedmont with a friend. I actually yelled at my buddy from 200 yards away. It’s funny how things work.
Anyways, great guy with some deep thinking. We talked a little about irunurun, especially sharing some experiences from Body Boss, and how he and his team are pivoting slightly towards building more sustainable habits after watching how users were tracking and engaging in their run-tracking platform. Now, irunurun is…

IRUNURUN is a performance and accountability app designed to help people and organizations achieve through focus, consistency, and accountability. 

If you’ve been reading my blog regularly or at least ​a few articles, you’ll know my interest in psychology and passion-pursuits. So Travis and I had a great talk, and it made me think more about building sustainable habits. But there was this one idea that really hit me and made a lot of sense — the Gap vs. the CHASM.
I wrote about Getting Over the Gap previously, but I hadn’t thought about the follow-up CHASM that exists. It makes sense. That is, getting over the gap is really tough, but getting over the chasm is REALLY, REALLY TOUGH. Crossing the chasm is consistently​ doing (vs. just doing) and can be referred to as “mastery”. This is where many people, I’ve seen not make it over.
I’ve seen entrepreneurs take the plunge and just after building an MVP (or oftentimes more than), watch traction not quite be where they dreamed, and they call it wraps without actually trying to find out why or how to pivot. There’s a saying to “fail fast”, but don’t quit prematurely. I’ve seen others find the financial burden of jumping off the original gap​ (and off a full-time gig) quickly swimming back to the full-time safety net. I don’t see enough people really endure and knock through walls where challenges exist; instead, wanting to turn back around. I’m not saying I’m not one of those to have turned around in some points, but maybe this opens my eyes on how to succeed.
Real back-of-the-napkin stuff right here… See the CHASM? It’s huge. Have your five steps grounded in your WHY to reach mastery
Travis described there being five stepping stones to help get over the chasm… each, anchored in a bedrock of some purpose — the “why”. I think my business school professor for an Innovation class would be thrilled to hear me say this. The five stepping blocks are:
  1. ​Clarity– What’s the goal? What’s the purpose? Who’s the team? Etc. This is mostly living and breathing and will need to adapt over time.
  2. Rhythm– Build a cadence that is sustainable, and sticking to it. I like to reflect on this story about how a guy did a “life hack” by getting up everyday at 4:30AM for 21 days. Except, he didn’t do it everyday straight. Instead, he focused on the weekdays because he knew that he couldn’t sustain early days on the weekends.
  3. Accountability– Who are you accountable to? For me, I’m accountable, largely, to me and I can usually drive my feet towards a goal. However, accountability can also come from work colleagues, friends, saying publicly you’re going to do something (like buddy Matt performing 100 asks for 100 days).
  4. Reinforcement– What enables you to consistently achieve what you need to achieve? In some ways, this can be the incentives. Lean more on the intrinsic vs. extrinsic motivators most will say.
  5. Leadership​ – In many ways in entrepreneurship, this can be you and kind of you alone. However, you can also lean on mentors and co-founders or even idols to lead you. Though, it’d best be someone or some example that you can have some direct interaction with.

​The five steps are from Travis, but the rest was in my terms of understanding. Let’s see if I got it right when he reads this (and potentially corrects me). The biggest stepping stones that I find people having trouble with is in Rhythm and perhaps the bedrock of their Purpose. Whether it’s finding time to workout in the morning, building a new business, or any other transformation, it’s imperative to find the balance that works for you (Rhythm). Part of that may include taking a step back and uncovering what it is that really drives you, not just motivates, but really DRIVES you (Purpose/ Why).
** As an aside and for bonus points, I thoroughly enjoyed Simon Sinek’s TED talk “Start with Why“. Good talk on what really drives people, and it’s not the “what” that a company does, but the “why”. My good friend Michael Flanigan, Co-Founder of innovation leaders Covello, recently shared his thoughts where in the [near] future companies will all need to have a humanizing element to be successful and sustainable.
What are your thoughts about the five steps to overcoming the CHASM? Are we missing a step? 
READY? FIRE! AIM… source: https://media.azpm.org/master/image/2012/4/6/2col-ff/civil-war_firing-line_fullframe.jpg
I’ve long known that I can be impulsive and highly engaged when I’m passionate about something. In one anecdote, I was helping a friend move and we were working on taking apart the bed. I immediately started to remove the screws and bolts until my friend just lifted the frame and showed it was a simpler operation. In startups, I’ve been hooked on an idea and gone door-to-door that afternoon with businesses to test the idea.
Then more recently, there’s the awkward opportunity where I open an email up, and start writing all sorts of incredibly deep, probably overzealous, and yet genuine message. It just so happened to span several hundred words long… whoops! Having a “ready, fire, aim” mentality is dangerous. Being that way at 2AM is a whole other level. As “How I Met Your Mother” showed, “nothing good happens after 2AM”.
source: http://media-cache-ec0.pinimg.com/736x/aa/13/77/aa1377e58ebffb0ac2d7a8c0d5594fd5.jpg
I was talking to an entrepreneur buddy recently about my overzealousness, he laughed, and said that it’s a common trait amongst entrepreneurs. It can be good, and it can be bad. Some reflections from this most recent experience and how to embrace and mitigate this mentality:
  • Can Impulse Be Sustainable? Everyone gets excited about something new from the get-go. However, is that impulse something that you can be excited about for weeks? Months? Years? Building a startup can be fun and in some ways, impulsive. However, the stamina required to continue a startup against the emotional, social, physical, etc. drains can be tough to overcome.
  • Co-Founders/ Trusted Mentors Can Limit the Risk. I’m not a fan of being a one-man band (solo-preneur). I’m somewhat doing it now with a new idea (I’ll share later), but it’s a long, lonely road. Being highly passionate and with a “ready, fire, aim” mentality (I’m calling it RFA from now on) doesn’t quite let me bounce ideas or have a great yin to my yang. Especially when it comes to having a technical partner, I’m nowhere as productive. My co-founders at Body Boss always gave great feedback, and there was always at least one person who played devil’s advocate. This really enabled the team to bounce ideas and think customer-oriented, design-focused, etc.
  • Passion Gives You Some Serious Freedom and Creativity. Like in my more recent passionate outburst, it can be hard for me to contain. It comes from a deep place within, and sometimes, that’s a really great thing. It can be highly inspiring for others while also incredibly liberating for you. Most people tend to hold back what they say or perhaps lack the words to put their thoughts into words (or actions). Being able to share can be an amazing way to share with others how you really feel. As a leader, this can be a powerful motivator.
  • I admit – I don’t always KNOW what I’m doing, but I BELIEVE in what I’m doing. True story. Building Body Boss, for example, was a great learning experience. I didn’t necessarily have “formal” sales practice in the past, but I could really feel what needed to be done. Everything from building and managing the pipeline to creating campaigns for outreach (to be known later as “drip marketing”) was all bore out of feeling. I’m certainly a man of conviction!
  • Don’t Overwhelm Others With Your Passions! Winston Churchill once said, “If I had more time, I would have written a shorter letter”. As I write my blog posts and crazy emails, I realize that I can be incredibly intense with how much I write. In fact, I’ve been called intense by a fair share of people. Oftentimes when I write a lot, it’s because I just sat down and started tip-tapping on my keyboard. If I take a little time out to think and let things digest, my words can be more concise and much easier to consume for the reader. In face-to-face settings, I need to work on listening more than speaking, even if it’s a passionate subject. Read: I should practice brevity and “passing the stick”.

Reflecting on my past, it’s clear how passionate I can get, and how they can quickly lead me down many paths. However, it’s important to temper those passions and that “ready, fire, aim” mentality with the right balance of conciseness and analytics. Analytics meaning being able to think holistically about areas and critically. Till then, I’ll need to also remember what my triggers are and put in the right stop-gates to mitigate sending crazy-long letters at 2AM even if they’re well-received. *phew* Write to the right audience! Or more generically, know your audience!
What are your thoughts about being passionate and the “ready, fire, aim” mentality? How would you practice a little patience and stem off potentially long diatribes to the wrong people?
I read a lot. Not books, but I read a lot of articles and blog posts and the like. When I do, I try to diversify a bit of what I read, but inevitably, I tend to read those that are more or less related to entrepreneurship, leadership, psychology, etc. Naturally, they tend to sound very similar to one another in some way, and I doubt mine is too different – except, sprinkle in some of my anecdotes and writing style.
So recently, I read a post about a corporate suit-turned-chef – “Fulfillment & Restoration Of The Soul”. But it tasted similar (see what I did there?) to other “pursue your passion” posts with a couple interesting points but one that really stood out. That is, the ending left me with a very, very interesting thought. So much so that I can’t get over it, and I have to write about it now – several hours after I read it but far before the Wednesday this post will eventually be published on.

“Maybe the trick is to make your passion a hobby first and see if you’re finding peace in it.” – simple, right?
A bit of an oversight on my part because whenever I wrote about passion-pursuits and the like, I always felt that it was superfluous to say, “it’s a hobby” or that you’re “living it”, when that’s not the case always. It really SHOULD be explicitly said. At least, that’s how I view it.
The way I’m interpreting this enlightening, yet maybe not so profound (?), piece of advice is simple… is your passion even something you can do as a hobby? Is it something you can find yourself doing repeatedly? Are you actually happy doing it repeatedly? Again, probably not so profound for you, but it’s interesting because as much as I think I know some subjects, it’s great to look at “familiar” things from another perspective and learn about it that way.
Okay, so you’re probably thinking, “Daryl, what the fudge are you talking about?” (Yes, those exact words.) Bear with me. I think the writer here is telling the readers to really try this “passion” that they feel they have. Sometimes, passions are really great interests, but not something you truly want to pursue.
Kind of like these winter melon pastries I get from the Philippines. When I get a couple packs, I freaking love them and will devour them in minutes. However, when I get a big bag of them, after a few packs, I’m disinterested.
It could even be something as simple as you love doing it, but you don’t want it to become your life. You don’t want that passion to creep into a business where now you live and breathe it, and then it ceases to be your passion.
If you really, really love doing analyses and cutting big data, and you think big data is your passion or social media marketing or technology are what drive you, make it a point to integrate elements of those in your life everyday. How’s that feel? Still excited? Are you finding yourself not that interested in new techs, new apps because you think you’ve seen them all? Then maybe technology in the marketing space isn’t where you should pursue an entrepreneurial endeavor.
Pursuing your passion via some entrepreneurial endeavor is great. It’s fantastic! Though, when you intertwine that “personal life” into your “business life” so it all just becomes “life”, maybe it’s not cracked up to be the right move for you after all. To figure that out, as the writer puts it, “make your passion a hobby first and see if you’re finding peace in it.”
Silly profound.