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15 realities after the start-up honeymoon

Starting a business is hard. The experience is different for everyone and, for many, the realities of post-start-up honeymoon hit quicker than for others. After a year of preliminary research and development, I launched matlen just over 2 years ago. I am not a raging success (yet). I have not struck it rich (unlikely). I am not featured in a major business publication as one of the great minds of our generation (never). I am, however, the common business owner — the regular, vulnerable, hopeful entrepreneur.

“Normal” entrepreneurs are not represented by the small sample portrayed in media. We are not all anomalies. We don’t all use the terms ‘hustle’, ‘hack’, and ‘secret-sauce’. We don’t all make it a point to don too-casual clothes to bring attention to ourselves. We don’t all have leading roles in start-up theatre. We don’t all use curse words during presentations to display an obvious, anti-corporate, “I answer to no one but me” demeanor. We don’t all open Macs while sipping lavish caffeinated concoctions by day, while, jumping feet-first into what appears to be a Michaleb Ultra commercial by night, every night.

In fact, the majority of us are stressed (good-stress and bad). The majority of us don’t have it all together. The majority of us are further down the left-side of the introvert-extrovert continuum than the minority may lead you to believe. The majority of us are high-achievers experiencing low-achievement levels for the first time. The majority of us are ready to sell-out and sulk back to corporate jobs more often than we’d like to admit. The majority of us struggle more often than we succeed…and it’s worth every minute, every dollar, and every lost brain cell.

Far too often, start-up owners and first-time entrepreneurs seek wisdom from proven experts; awe-inspiring leaders of lucrative start-ups, or, ‘started-from-the-bottom-now-we-here’ fairy tales. When I began, I was no different. After a few short years, however, I’ve learned that the best lessons come from those who are still figuring it all out, still in the trenches, still at the bottom of the growth curve. These are the real experiences. Our stories are humbly unaffected by a ‘rose-colored-glasses’ version of how success was conquered (past tense) but, on the contrary, are entirely inspired and driven by how success will be found (future tense). I am you, the common entrepreneur, 2-3 years in the future — these are my observations (not advice) of “reality” that I wish I’d received on launch day. 


This may sound harsh but hear me out: your family and friends will not be the reason you grow or fall flat. Sure, they may be first in line to see you cut the inauguration ribbon and they will more than likely be there to provide you motivation, inspiration and, sometimes, even money. Although they may be your biggest advocates, THEY ARE NOT YOUR BUSINESS DEVELOPMENT EXECUTIVES. If there is something you need, be sure to ask and, of course, they will help. Otherwise, don’t expect that your business will be the first topic of conversation among your inner and/or extended social circles. The number of friends in your social network is not a predictor of your potential client base or even representative market size — and that’s perfectly OK.

The reality: your family and friends will support YOU regardless of your chosen career.


Social media is a funny thing. Don’t ever forget: social media is a form of MEDIA, the accuracy, thereof, is always biased, partially true and, sometimes, completely inaccurate (at the risk of making a “fake news” Trump comment). You will, inevitably, be required to dip a toe in the vast world of content marketing at some point in your entrepreneur journey (blogs, articles, videos, e-books, podcasts, online courses, etc.). My observation: don’t be afraid of the crickets. Clearly, I am not a maven of digital marketing. I don’t have a vast following and my ‘likes’ and ‘shares’ are few and far between at this stage of my (ad)venture. Despite the adrenaline rush I may receive when my content is shared, I have learned that it is not an indication of traction in the market — despite what social media and digital marketers may suggest. I have seen (and worked with) multi-million dollar companies who have a negligible base of followers and abysmal social media engagement. However, these same companies have a strong, dedicated client base and healthy, recurring revenue which leads to profit almost every year. On the flip side, I have also been witness to companies who have a phenomenal ability to engage a vast audience on social media and, yet, they struggle with the concept of monetization.

The reality: don’t be afraid of the crickets when it appears your content is falling on deaf ears — you never know who’s watching. the reality: despite your number of likes and shares, the follower quantity doesn’t represent profitability.


I cannot count the number of times I’ve walked around my home staring out the windows while I thought about my company. How can I make this piece of the business better? How can I find more clients? What's the wisest way to spend my money? Is there an additional business idea I should pursue? Hours (and even days) go by and my mind has taken me on a complete tangent while my whiteboard list of “key priorities” remains untouched.

For the longest time, I would be overcome by an incurable feeling of guilt: guilt for wasted time, guilt for focusing on non-priorities, guilt for not getting as much done as I wanted to get done.

The reality: these unplanned thinking engagements result in the culmination of new ideas, innovation and progress; the qualities which make entrepreneurs so valuable. Lose the guilt. Thinking is a vital aspect of your job, so, accept it. It’s those who don’t walk around their home thinking about new ways to improve their business that end up failing the quickest.


Sparing you any unwanted visuals, perhaps the biggest shock to the system after the start-up honeymoon phase is the realization that you’re alone, naked, without any trees to hide behind. Your mistakes are your mistakes — and everyone will see them. Your failures are public — and everyone will see them. Your weaknesses are exposed — and everyone will see them. It’s you, buck naked. Sure, you may not be a solo-preneur and, as such, you may have a solid team to back you up or even a partner to help share the load. You will also have access to great resources devoted to supporting you and increasing your likelihood for success.

However, the reality is: be prepared to wander into the world of vulnerability, without multiple layers of corporate protection to use as a scapegoat for those times when you look more human than ever before. 


If you’re an aspiring entrepreneur looking to start a new business in hopes of leaving corporate politics behind, you may want to revisit your reasons for leaving your current job. The startup/entrepreneur ecosystem is, quite literally, one big corporation with a heck of a lot of sub-divisions. There are still political echelons (look at how many companies I’ve started; look at how many users/clients my company has; look at how much money we’ve raised, etc.). There is still political favoritism (I’ll award the contract to Jane Company X because they have a major client to whom I’d like to be introduced). There is still a political popularity contest (Joe Company X has received a lot of press lately, I should get connected to share in the limelight) and so on and so on.

The reality: running your own business means selling, and selling means that politics will always be at the table. Knowing the kind of person you are (and aspire to be) as well as the type of business you intend to run is every bit important to entrepreneurs as it is to players of the corporate jigsaw.


If you’re currently working in a corporate environment, chances are you experience all the typical stress triggers: finding a balanced lifestyle, accommodating long hours, pressures from deadlines, people/communication dynamics, resource limitations, etc. Dealing with stress in such an environment is, well, stressful. If you think jumping out on your own will alleviate these kinds of pressures, think again. Here’s the difference: doing what you love (your terms, your timing) turns bad stress into good stress. It’s incredible how the same activities can, all of a sudden, become enjoyable when you have bought into the purpose.

The reality: stress will always exist — it’s fulfillment that often eludes us when we continue to pursue that for which we lack desire. 


Too many start-up owners dig their heels into the ground of their initial idea. Their decision to become self-employed is predicated on the fact that a particular business idea will be their ticket to freedom and success. Truth be told: even if you have a stellar idea, market uptake is never guaranteed and can often move at a snail’s pace (at best). Don’t buy into the “never quit” ethos — knowing when to jump ship is something you should determine before you launch. If something doesn’t work, it doesn’t mean you’re not cut out to be an entrepreneur, it means your idea was a poor fit (timing, market need, competitively, etc., you name it).

The reality: cutting your losses, changing your business model, and/or making a complete pivot that sends you in an entirely new direction, shows wisdom, not weakness.


There really is no better way to describe this reality than through an example. Last summer, a friend and I had planned a round of golf for a Friday afternoon. We approached another individual and asked if he wanted to join. His response was as offensive as it is common: “Sorry, some of us actually have to work for a living”. What made this individual appear to be even more obtuse was the fact that, he too, was a self-employed owner (albeit in a more traditional, brick and mortar model).

The reality: be prepared for ignorance. The world is only now being introduced to the gig economy and to those who, collectively, agree that there is more to life than the shackles of traditional careers. Indeed, we don’t “work for a living”; we choose to work in order to enjoy living.


There are two key perils that come with the inability to turn off your brain: social sabotage and ingenuity burnout.

Social sabotage is the negative impact on your family and friends resulting from your inability to stop talking about your business and all the ideas you’d like to implement today, tomorrow and in the future. Fact: no one ever cares as much about your business as you do. Make an effort to stay in touch with the world outside of your new world. Don’t turn into an entrepre-hermit.

Ingenuity burnout is a self-inflicted, harmful cycle of “good idea-better idea-even better idea- still nothing executed”. Often time, entrepreneurs are sucked into the vortex of new ideas, innovation and “disruptive” business models (yes, note the quotation marks). Trying (and thinking) about such concepts is often like running on a treadmill — you’ve expelled a lot of energy to end up where you began. There exists, what I like to refer to as, the “think-do” continuum. It’s important to (quickly) find a balance point on this continuum and to teach yourself (and team) to identify when you’re overloading on too much thinking.

The reality: sometimes, you just need to turn off your brain to get things done.


Be 100%, absolutely, no-questions-asked, positively, certain about what you value more: immediate freedom OR immediate money. Sure, there are examples of entrepreneurs who were able to hit their stride out of the gate and, thus, were able to obtain both immediate freedom and immediate money. However, for your own mental well-being, it is important for you to perceive such people as unicorns — don’t be lured into the beauty to which only few are privy. Anomalies are inspiring but don’t forget: they’re anomalies. Too many start-up owners expect to find immediate financial freedom but instead find themselves quickly lured back to their former life with a steady paycheque.

The reality: if you want to start a business, do it for the freedom in hopes of finding money — not the other way around.


The reality: Self-explanatory. Literally, schedule a 20 minute, weekly rant with someone you trust. Getting it off your chest is therapeutic.


Sounds a bit harsh and bitter, right? However, just like getting passed over for a deserving promotion for which only you are truly qualified, sometimes morons will succeed while you struggle to find your way. There exists a plethora of reasons for why this may occur but, indeed, it will happen, it will sting, and you will have to absorb it and move on.

The reality: luck exists for everyone except for the morons who tell themselves luck had nothing to do with it.


If you conduct your pre-launch research properly, be sure to blatantly invoke questions pertaining to the monetization of your product/service. Finding people who like and support your concept is one thing. Finding people who like and support your concept with their wallets is another. If your research indicates 1000 people who are willing to pay for your product/service, expect that 10 will actually pay.

The reality: the importance of conservatively projecting your cash flow is essential.


I’ve come across a lot of business owners who appear to “have it all together”. I have been witness to the same owners struggle to get out of debt, gain any form of market traction, and, sadly, many of whom did not survive the chaotic world of entrepreneurship. I’ve said it before: allow yourself (your company) to be vulnerable for the sake of improvement.

The reality: if you need help, ask for it and if you begin to drown, accept the rescue. Furthermore, learn to identify confidence over-compensation in others — offer to help despite it, rather than ignoring in spite of it.


Great. All of these realities are nice to know but the real question is always the same: is it really worth it? It sounds like a lot of work and an extreme tug-of-war between emotions and opportunity cost. That’s because it is.

Here’s the ultimate reality: sometimes, I miss having a job description with a defined mandate. Sometimes, I miss having a steady, healthy paycheque. Sometimes, I miss the support system of a larger organization. Sometimes, I miss the benefits of working for an established brand. Sometimes, I miss business travel, expenses paid by the company, nice hotels, and a per diem meal allowance. Sometimes, I miss the luxury of not having to work at 100% effort 100% of the time (yes, I said it).

However, (and I believe I speak for many common entrepreneurs) I believe freedom is worth the sacrifice of pseudo-certainty, predictable income, and fabricated status. I prefer complete, untamed autonomy. I enjoy not having a fixed office space or 'office hours'. I choose to replace steady income with a steady workout time. I revel in the ability to replace dated traditions and ludicrous policies with relevant logic. I don’t believe in vacation days, sick days and “time-in-lieu”, instead, I believe in being a responsible adult, fully aware of my own, personal capacity, limitations, and when I'm feeling inspired and in the zone. My quarterly bonus is received as a daily dividend in the form of dropping off my children every morning and being home when they arrive to tell me of everything epic from schoolyard politics.

So, after the start-up honeymoon phase, is it still worth it? I guess it depends on what you aspire to be. Why don’t you ask that nagging voice in your head?


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