How to Know When it’s Time to Walk Away

Ah, the BIG question that no one likes to answer: when is it time to walk away?  To many, this question is the ultimate slap in the face.  As has happened to countless entrepreneurs – you are approached by any number of friends, acquaintances, distant family members, etc., (who may know very little about starting a business) with the frustration-inducing question – “So, when do you think it’s time to move on?”   This question is irritating on a number of levels, most notably because 99.9% of the general population assumes, based on popular culture, media, etc. that every single day, startup companies are acquired for billions of dollars, and their founders thrust into instant fame and glory.  Therefore, if you are toiling on a business for more than 12 months, without achieving millionaire-status, certainly you are destined to fail and therefore should resort to another line of work, and permanently extinguish any memories of that ill-thought endeavor.

Of course, my natural inclination here is to write some retort about disproving the obnoxious doubters and skeptics, whom are largely the ones asking this question, but I digress, as that is another post in itself.

Back to the question at hand.  Seriously, how do you know when it’s time to walk away?  As I have tirelessly admitted – I have done a deplorable job at keeping up this blog.  But, fast-forward from my last post, and I myself had been faced with this same question.  Thinking through the potential decision to walk away from the business, I continually came back to the same consistent answers.  Being that I am a big believer in “going with your gut” I took stock in those thoughts, and ultimately made the decision to stepdown from the startup I had co-founded.  It’s never an easy decision, and there is not a one-size fits all solution.  Each and every entrepreneur and business owner needs to think critically and objectively about their individual situation and logically arrive at the best decision to move forward.

In my opinion, however, there are a few essential areas that will provide clarity to a “leave or stay” decision.  I have found some of the best solutions are to be a devil’s advocate with yourself… and truthfully, doing just that can promote some seriously sound decisions.  How to know when it’s time to walk away is one of the most (if not the most) under-rated, but incredibly important questions to ask.  Here are the top five questions I’ve asked myself before deciding to walk away:

  1. Why are you asking the question to begin with? This is not meant to be a satirical question.  Think about it – if things were going well, you wouldn’t be thinking of walking away, right?  Or, would you?  Are you thinking of quitting because the product isn’t working?  Because your sales aren’t growing?  Customers aren’t buying?  Investors aren’t making offers?  You’re running out of cash?  You’re unmotivated?  Find the reason – it is a huge first step.
  2. Are you meeting your milestones? Another tremendously under-rated question.  Seriously though, I’m amazed at how common this problem (of not attaining goals) is.  Any intelligent investor is going to ask, and if you aren’t reaching your goals; be it customer acquisition, partner retention, or good old-fashioned sales, you need to figure out why you’re not hitting them.  Or, in the even worse scenario, you don’t even have any goals, milestones – which is an even larger red flag.  Assuming you do, why aren’t you hitting them?  Answering this specific question should be a separate post, but if you’re missing your targets repeatedly, that could be a sign that you need to exit (notice I said “could” be).
  3. How are your business partner relationships? If you have a business partner, what is the relationship like?  More specifically, are you able to work together?  Do you agree on long-term goals for the company?  Short-term implementation strategy?  Do you get along in a business context?  Partner tensions are one of the largest causes for startup failure and/or split-up.  Assessing the day-in-day-out working relationship with your business partner is a necessity.  Long run – what implications could be made about the business’ success if things stayed the way they are.  As a company grows, so do the problems.  Correcting issues now (or choosing to walk away) could save a tremendous headache later on.
  4. If the business blew up, and you had quit, would you be okay with that? If some of the above questions are under-rated, this one would have to be one of the most over-rated question asked.  Regardless, it aided in my decision, only because I was asked countless times.  I get it, everyone wants to know – if your company worth skyrocketed to the hundreds of millions, and you weren’t a part of it, would you hate yourself?  The reason I say this question is over-rated is that it’s somewhat ridiculous.  If you would make millions next year but instead, didn’t, would you be disappointed?  I would think the answer is an obvious, yes.  There would be disappointment certainly.  But, it’s just not that simple.  If the business were on the verge of blowing up, most likely, you wouldn’t be contemplating quitting.  And, if you were still thinking of quitting, that would imply that there were serious concerns outside of your future financial well-being.  Point is, what got you to this decision point is probably one of the above issues.  The reason people hang on to this question so much is that they obsess over the “what if’s”.  IF the hugely improbable happened, then…  This is just not logical thinking.  The bigger picture is that, in this scenario, your only motivation is financial and you are treating your business purely as a lottery ticket, but with a lot more required from you.
  5. Do you still care? Is the fire there?  Yes, I realize this sounds like a witty rhyme, but it makes sense.  Do you get up excited to work on your business?  Do you still enjoy what you’re working on?  Do the reasons that you started the company still stand?  Has the company become what you thought it would?  This last question will usually be the final straw.  Missing milestones, partner disagreements, lack of growing revenue, and customer issues, may begin piling up, but will ultimately result in you losing interest and even motivation.  The fire is gone, as is your desire for the business to succeed.  It never starts with this, but it often ends that way.

In the end, each founder needs to make a decision that is right for them.  These are five of the self-reflective questions and reasons that I chose to walk away, but just because one individual leaves their startup, doesn’t mean that you should too.  Sometimes hanging in there, and finding answers or solutions to the above questions is exactly what you need to do, and will be the spark plug to incite change in your company.  Other times, patterns emerge and regardless of what changes you try to make, time keeps slipping away without results.  Analyze the reasons, as I suggested above, and make the decision.  Lingering on the pain points for months (or years) on end, often does not make the decision easier.

Lastly, and on a positive note, just because you have moved on (or even massively failed) on your first attempt, does not mean your next endeavor won’t succeed.  And that is horrible advice, if anyone tells you otherwise.  And, in the same breath, past success doesn’t guarantee future performance either.  If you walk away from your startup, as I have, pick yourself up, move on to your next project with enthusiasm, and most of all, take with you, the lessons you’ve learned from the last one.

NOTE: Thanks for checking in!  I no longer keep this blog up to date on a routine basis.  While I will occasionally write updates here, it is not regular.  I have switched all publications over to our new venture, Fuel Your Mission, focused on equipping individuals with tools to succeed in their careers and businesses.  Be sure to follow us over there to stay up to date!

4 Ways That Getting a Job Helped My Startup

Unfortunately, in many minds, a full-time job rebels against any form of entrepreneurship. Like an un-tucked shirt in a prep school, an entrepreneur with a full-time job goes against the grain. In a modern world, where we set parameters and stereotypes for every possible thing imaginable, a full-time employee can’t possibly be a “real” entrepreneur. Right? Recklessly flittering away any savings and donations of family and friend, while tirelessly working on idea after idea with hopeless abandon is certainly more respectable than a part-time entrepreneur distracted by a full-time job. Polar extremes, I realize, but you get my point. But this mindset is flawed.

I don’t believe for a second that there is a definite “right” and “wrong” way of becoming an entrepreneur. However, I absolutely do believe that many startup founders would be so much better, if they did take a (or keep the existing) full-time job while launching their business. In many of my previous posts, I have mentioned my strange start, which did involve cold turkey quitting of a good job. A lot has happened since, and I have recently found myself full-time employed again, and happy.

There are unbelievable benefits reaped when I returned to a full-time job. While the list could fill this page, I kept the impact to 4 ways that getting a job helped my startup:

  1. Increases Focus – When I was in the throes of co-founding a startup, I was also trying to pick up consulting projects to pay the bills; all while anticipate the birth of our first child. I was stressed (but don’t tell anyone). Guess what I had none of? Focus. It was non-existent. I was scrambling like a wild-eyed retiree at a yard sale. I wasn’t on point with my tasks, and it cost me. Which stressed me out more. In a conversation with a college friend of mine, he summed it up perfectly, “You can’t focus on long term goals while your short term needs aren’t being met.” That was exactly right. Something had to change.  When I took the full-time job, it literally changed my mindset instantaneously. I slept well that night. At first sight, the tangible benefits I hadn’t had in over 18 months were amazing. Consistent paycheck, healthcare benefits, etc. But, what was also inherited was a new adherence to a schedule and better discipline. I had a set task in front of me each day. I no longer had to debate at which level of desperation each of my tasks were. I was committed to an employer to provide a service, and that commitment gave me more focus on my startup during after-work hours as well.
  1. Encourages Creative Thinking – Contrary to what popular culture depicts, a startup environment is not constant creativity. There are things that suck, and tasks that are boring, but need to get done. Setting up bank accounts, phone numbers, CRM systems, paying bills, spending money on business needs with no budget. But then there’s amazing upside of course. When I took a job as a marketing manager of a large technology company, all the creative process used in Mango was spilt over into my day job. I had an open mind to do my job better, and work in higher collaboration with my teammates and clients. And it worked in reverse too. During my work hours, I created proposals and executable plans that adhered to business strategy objectives, and metric-driven goals, while keeping high creativity. Shockingly, the same goes for starting a business. This day-in-day-out performance turned around and enhanced the objectives and direction of our startup as well.
  1. Maintains Accountability – I’ve heard it said that accountability (or lack thereof) will either help a startup succeed or help it fail. I whole-heartedly agree. An idea itself is absolutely meaningless. The best business and marketing plan in the world will fail, without execution behind it. And to that end, execution is reinforced with accountability. I have admittedly struggled in this area, at times. Juggling several tasks, let alone different roles in different projects leaves you disorganized. Putting out fires as they pop up constantly is horrible. Having a job again, forced me into holding account for my waking hours spent. I manage my schedule and personal time with so much scrutiny. Sure, I fail often (especially if Blacklist is on), but I am on-point with what I do during the day. Being certain to execute what I need to accomplish for my employer. I don’t waste my time, because it is a precious commodity to me. When the switch flips in the evening, and I shift over to startup, I am more diligent and on-point, because I have been exercising that drive and accountability all day. And vice-versa in the early morning hours, when I “check in” to my day job. This has been an invaluable benefit to me this past year.
  1. Reminder of Motive – In the flurry of life, sometimes it’s easy to forget what we’re working for.   We “do the work” in part, because we’re lost without it, and rarely question why we do what we do. Sad really. Without a motive for our efforts, we are literally like the metaphorical hamster on a wheel. I am a huge proponent of occasional pauses in life, to assess circumstances and surrounding. Like so many, I have a family I love very much. Their needs are greater than mine. Always. I will do whatever I have to do to protect those needs. That reason, combined with my personal faith and convictions to do work that matters, was all the reminder of motive I needed. Accepting that full-time job gave me a refreshing reminder of what I was working for. This self-awareness is critical.

So, I’ll take my shirt untucked, thank you, and work my full-time job, while managing my time and resources wisely to continue to further my business as well. Getting a job has helped my startup. It can be done, and don’t let anyone tell you otherwise. To each his own, but I can certainly speak for the tremendous value gained from working a full-time job while in startup mode.


NOTE: Thanks for checking in!  I no longer keep this blog up to date on a routine basis.  While I will occasionally write updates here, it is not regular.  I have switched all publications over to our new venture, Fuel Your Mission, focused on equipping individuals with tools to succeed in their careers and businesses.  Be sure to follow us over there to stay up to date!

The 4 Most Important Lessons I’ve Learned Being a Broke Entrepreneur

The words “being a broke entrepreneur” are tough to say. As I’m typing this out, a gut-wrenching feeling comes over me. Reminders of grueling anxiety, heightened confusion, and desperation, rush back easily. I think of days being unbelievably distracted. Too much to do, too little time, and not a clue on what to tackle first. Discouraging days, followed by afternoons of incredible excitement, and then repeating all over again at random. Going out on your own, as many of you will attest, is rough. It’s easy to stand on the sidelines and watch, critique, judge, and point fingers, but playing the game and grinding day by day as your business starts at ground zero, is incredibly difficult.

One of the most challenging things that most entrepreneurs encounter is loss of financial security. Certainly at inception, this is a common peril. Sacrificing comfort, security, and consistency of a paycheck is a pill not swallowed easily. When I left my corporate job initially, I thought I understood the impacts. To summarize the 6-12 months that followed – ouch! Initially swept up in the “this is something I’ve got to do” mentality, the reality sinks in that giving up the paycheck is hard to do. My wife and I were pretty darn near close to broke, and that’s before we had our baby. Financial instability clouded my vision, distracted me, kept me up at night, and left me dazed and confused at times. But, like most things in life, there are lessons to be learned in the midst of difficulty. The 4 most important lessons I’ve learned from being a broke entrepreneur have been helpful moving me forward.

  1. Lends Perspective – Working in a corporate job grants us many luxuries, that we commonly call necessities. Health insurance, 401k, term life polices, low deductibles, routine paychecks, and more. All good things. It also provides comfort in terms of career security and even personal identity for many. With some of those luxuries stripped away, I realized how raw starting a business really is, and what gets taken for granted under the banner of a large company. Company names gave me an identity, at least at times. It’s instant credibility and reputation. Heck, GE is running an ad campaign with this logic. The perspective that I gained was tremendous in many ways. More appreciation for things easily taken for granted. A respect for those other self-starters. An understanding of how truly hard it is to start and succeed as an entrepreneur. Maybe greatest of all was thankfulness for what I did have versus dwelling on what I did not.
  2. Strengthens Work Ethic – Being 100% self-dependent for the progress of your startup produces an accountability and efficiency with the work you do. While any successful venture draws on the work of multiple individuals or teams, when you are starting out, the responsibility lies with you to divide the workload. Decide where you do and do not need help and set a plan of accomplishing the tasks. That “sink or swim” mentality is incredibly more intense in the survivalist life of a startup.
  3. Exposes Weakness – Our flaws tend to hide when we’re absorbed in a large environment. Our job roles can at times keep us confined to a particular set of skill sets and even a lack of skill sets. Programmed to conduct our jobs and stay within the lines and framework of our prescribed duties, we typically are not able to see our shortcomings or opportunities for personal development. Starting a company is raw, and you’re either all-in, or out. There is no job role, until you create one. This is a vulnerable spot to be, but it forces self-awareness. Self-awareness is critical.
  4. Reinforces Motivation – A young business or entrepreneur for that matter, will never survive if they’re unable to find their source of strength. Contrary to popular culture starting a business is rarely an overnight success, but a long fought battle. Stamina is king. If you don’t know what motivates you, you’re going to drown. When things become difficult, your motivation gives you the strength to persist, period.

These are pivotal moments when you (and I) can look back at a time that was excruciatingly difficult and come away with lessons to encourage you moving forward. As difficult as it is to admit, I am thankful that I spent time in the “very broke” stage of life, and survived to tell the tale. In my opinion if you don’t learn anything from a struggle, you’ve lost.

NOTE: Thanks for checking in!  I no longer keep this blog up to date on a routine basis.  While I will occasionally write updates here, it is not regular.  I have switched all publications over to our new venture, Fuel Your Mission, focused on equipping individuals with tools to succeed in their careers and businesses.  Be sure to follow us over there to stay up to date!

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