Lessons of a Self-Motivated Person Working in Tech for Over 15 Years

A journey and insight exploration
March 14, 2023 by
Lessons of a Self-Motivated Person Working in Tech for Over 15 Years

Here's insights to consider before getting into anything tech related (yes, that means you, too, GPT-ers) from someone who started as a freelancer and worked up to the Director level in the corpo world.

I am pleased to announce that my wife, the CEO of the company Kief Studio, and myself, now the COO of Kief Studio, don't deal with the nonsense anymore. If you want to go down that rabbit hole, by all means, the insights in this reading will undoubtedly put some things in perspective and help you choose your path.

Never Go All in on Being a 'Brand Driven Buyer'... or Worker

Oh, have you seen the latest (insert--new-tech-product-name-here)? They added in (x,y,z) features and even upgraded (a,b,c)!

Yea, I've seen it, but I've also seen the same stuff every time a product launches. Guess what happens in tech all the time? Improvements, cutting-edge ideas, and better features. That doesn't always mean better overall, helpful, or even creating long-term ability expansion.

You need to visualize the standpoint of a consumer one year from now. If it passes that test, make it two years. Going beyond two years is fundamentally flawed since predictive analysis becomes more like guessing at that point.

From an Employee Position

Evaluate contract offers from companies in those one-year and two-year terms. Do not sign employment contracts with companies that can't pass that simple test. It'll be a barrage of PR campaigns discussing the uniqueness of the product and company. You'll be on top of the world, getting all the recognition and praise you always wanted in your field, and then you'll be disappointed.

The subsequent layoffs from either failed product launches, overspending, the breakroom being just a space with no time limits for hanging out with friends, or someone else will make something that is just better is all very likely.

It happens all the time. Young entrepreneurs (and some older ones) get their big break in the tech scene. They love the glam that comes with a successful launch. Then their mission magically changes into 'Being a role model for the tech world' instead of just building good products with real-world practicality. Be mindful of any contract that goes beyond six months.

Start with a W-9, not a W-2

Start with a six-month w-9 contract, get the vibe, and research the management, investors, and public perception. If you see any trends toward the dark side of tech, do not renew the six-month contract. Get paid and get out. You have all the networking connections necessary and leave on good terms, don't be a jackass in the office (even virtual - ask who plays games you like, ezpz), and make some real friends.

Research The Managers

It would help if you got in-depth here. You should Know everything and more than what they know about you. Use social media, public records, Search Engines, etc.

Why Research the Managers?

When researching potential managers, dropping your expectations by about 25% is wise until they have earned your respect. Remember, respect is earned, not given. Just because they have a good (or bad) track record doesn't mean much about how they will interact with you. This approach can help you maintain a better mental state, even if the project is less than stellar, and you won't resent them. However, if the project and team are fantastic, don't hesitate to go all in.

Realistically, two weeks is often enough to determine whether the project is worthwhile for an 'all-in, #team-no-sleep' approach. While some managers may not be terrible, they may lack the skills or knowledge to manage the project effectively. If no progress is made after two weeks, that's a red flag.

How to Navigate Bad Managers

Remember that the company needs your help, they put a budget towards hiring someone with your skills, and they picked you. That also means you can provide valuable support by taking on some of your manager's responsibilities. They wouldn't have needed more people if that manager could handle the responsibilities and workload. It's essential to approach this positively and helpfully to advance the company's position within your field. Remember that it can be difficult to manage someone more skilled or knowledgeable. In these situations, organizing a meeting to analyze the challenges and suggest building a team to take the challenges on may be helpful. Besides, it gives the manager another group they are "in charge of" on the company record. Win-win.

High Risk, High Reward Positioning

The following is a risk-to-reward scenario. Read the room. If you can't read the room, bring in someone who can. If it's a 'mission failure imminent' situation and you understand how to fix the problem, and your manager is the roadblock, bring in their manager. Just bring your A-game, and you better be 100% correct. If you don't, you will get messed with by the lousy manager and, ultimately, fired. I've seen this play out both ways, and I've also seen this method used, and the manager's manager was terrible too.

What if the Manager's Manager is Also Bad

If their manager is terrible too, escalate all the way up because, at this point, you'll get canned unless you can find someone higher up in the chain that sees your capability, vision, and the problem you can solve. This is never to be done for mundane things. If it's something that is losing the company money and isn't a cog in an overarching business strategy, it's not mundane. You need to know that project just as well as the person who originally conceived it, and you need to know precisely what part of the business strategy it does or does not align with.

Alternative Escalation Method

Bring it to someone higher up in the finance department, they'll do the alarm bells on your behalf, and they'll be your new buddy since you made them look good, and you look good because you have the solution ready to go.

I Quit a Cannabis Tech Job at 6 Months

The red flags I missed when I got involved in it

As someone who quit a tech position at a cannabis company, I can attest to the importance of recognizing poor management practices. While the company had a great idea and decent execution, the C-Suite micromanaged all projects (that's what I missed in my research) and filled my week with pointless meetings without producing one viable budget discussion. They wanted to do everything exactly how they wanted it done and not spend a dime on it.

Some Success Comes from Luck

The owner was part of the 'right place, right time' crowd in the late 90s. He bought a bunch of equipment and re-sold it at a markup, priced into the installation service. He purchased the equipment to install everything after closing the deals to install it, so he never had cash on hand to manage. It was all 'per project' stuff. The news media discussed this equipment becoming necessary, and he made some cash. It could have just as easily never materialized or been out-hustled by a competitor.

Right Place at the Right Time: Luck or Skill?

Granted, you need to be in the right place at the right time, with the right product, to succeed. You could argue that is a positioning skill, but I'll be transparent. After what I saw in the office from a complete lack of managerial, business, math, people skills, and software skills, I'm betting it was pure luck. The gift of gab and a willingness to hustle without much else going on there.

That's not enough long-term. This leadership style requires the staff to control their projects and manage their teams completely. If you don't want to take the time to learn how it's done, you don't get to dictate how it's done. You'll fail way more than you would if you listen to the people who know what you don't. Don't trust anyone? Don't hire anyone.

How to Be a Better Leader if You're a 'Hustle' Boss

This type of leader must become a motivator while focusing on optimizations to the hustle. It also requires a selfless approach. The team has to come first. Otherwise, the other shortcomings will lead to a lack of trust in ability, leading the team to quit, just like I did.

Check Your Manager's Personal Social Media

I'm not gonna knock the hustle, I dig it, but as far as business was concerned, he had no experience aside from elementary margin math. I would have known this if I had researched social media more before signing the agreement. I wouldn't have worked for them if I had seen that first. A lesson learned, for sure.

They wanted to build this massive, data-less set of projects because they 'sounded like a good idea.' It would cost thousands more in staffing and equipment in the long run. The solution was to fix what they already had, not to add more.

Fix Losing Money First. The Rest Comes After

The company was losing money daily. Fix the losing money problem, then add on more projects. Those decisions are made by analyzing the cash flow and available data. Cut costs, optimize processes, then re-allocate what becomes available to new projects. Basic stuff. This disconnect gave me a few red flags:

  1. They didn't understand basic business principles.
  2. They lost sight of people. Without sight of people, the company can't see its customers. If the company can't see its customers, it can't speak to them. If the company can't talk to them, the customers won't shop with the company.
  3. They had no money left. One of my roles was marketing, but I also needed to build the whole tech suite involved in that process. That costs money. They didn't approve budgets or talk about them at all. They just breezed past it like that was out of the question. That's a telltale sign they have no money.
  4. They make decisions without analyzing data. You can't run a business without analyzing data at some point. Better companies do it every day and adjust as needed.

Data For The Win

I tried to salvage the situation from the inevitable financial disaster. I gave them a full rundown of how we could amplify one aspect of the business, their website, with a gain of ~20% in shopper loyalty and a ~40% increase in customer acquisition, which would ultimately snowball through a feedback loop as long as we maintained that path. That required me to have a budget for some software or time to build a custom solution we could use. They didn't do it.

If the Company Buys Random Things that Don't Drive Profits, you Should Run the Other Way.

Aesthetics are fantastic, and it's fun to say, 'Hey, look at this cool thing I got' sometimes, but this is a losing strategy in business. They were buying decorations for the walls that cost thousands of dollars. It took over a month of setup time, which cost them thousands in staff requirements.

When you don't have funds for the basics, buying aesthetics that nobody will see because you didn't put money towards getting people through the door to see it is a bad idea.

I know what you're thinking, nobody running a business would be that stupid with their investor's cash, buying wall decorations for thousands of dollars and overstaffing when they are hemorrhaging money and owe investors millions. Still, yes, that's a true story.

Either way, they needed to cut costs on other business areas not producing revenue. They always had 5-6 employees on the floor doing nothing. That is necessary to stop first. Frivolous spending on equipment was a close second.

Use the newly available cash to pad the project plan with a decent enough budget, then re-establish the areas that had cutbacks as we created the feedback loop since they were personal 'nice to haves' and not 'need to haves.' Once the money comes back, add the staff hours back. You then realize the other expenses were unnecessary and don't buy them.

Incompetence Became Clear

They didn't look at the data. That's when I clearly understood I was the only person in the room with any real-world business experience. That's never good if you're not the employer. Creating a productive environment down the road after trudging through the un-relenting micromanagement was not possible since the micromanagement was the source of the lost revenue. That's when I decided to quit that job. Besides, my wife started her creative marketing agency and wanted me to join her. It was an easy choice.

Research The Investors

As an employee, the best friends you can make are the investors. Especially if you have a capability that is valuable to some of the companies they invest in.

Investors become your boss's boss very quickly in companies at these stages. They know what budgets are allocated, what projects are going on, and who everyone is. They fund the tasks as they are built to get a higher payout.

Know How Investors Work

A company investor is an exciting role. Essentially, you give someone money because you believe in their ability to do something, with the promise of them returning your money with additional funds for the support. The concept is simple. The relationship is not.

If a company isn't profitable, and that investor is not skilled in running a business of that nature, then this is a prime opportunity for you, their problem-solver friend, to take over the project.

Profit Misses are A Big Deal. Here's Why

Let's say you work at a company that is hemorrhaging money. If an investor is involved and keeps pumping in cash, that's a red flag, especially for the C-Suite. The investor can take the company if they kick in enough to own more than 50% of the company.

If You're The Best, Here's Your Chance To Prove It

They can then arrange with you, their cash flow problem solver, to step in and take over. Be ready for litigation and a lot of headaches, the investor will likely cover the costs upfront, but you'll owe them big.

Where's The Money?

The money owed hasn't been realized due to bad management, so you have grounds to fire the company's previous owner. When you look at it from a business perspective, it's the right thing to do if the investor is not getting back what they are owed.

The Boss's New Boss Approach

Alternatively, you can be their boss, which can be a better play since you won't have to pay the severance package, and you can teach them the right way to run it while you get paid more than they do. Respect is earned, not given. All the work they do after that boosts your bank account if they are capable.

If they aren't, it might be better to take the financial hit of the severance package. Evaluate this scenario carefully, and consider personality types to analyze risks, including your own.

What Are The Business Ethics Involved Here?

From a personal ethics standpoint, you must ask yourself if you dare to do this and still sleep at night. Bad managers make it easy to say yes to the 'can I sleep' ethics questions. It's what is known as a hostile takeover in the business world. It happens very often at companies in these stages.

Be friends with your investors, and if they give you signs that they don't want to be your friend or use clever NLP tricks to make themselves approachable without going beyond an acquaintance, be aware this is likely what they will do. It's way cheaper to do this than it is to build a company from scratch. It's just business.

What Drives These Investors?

Money and the opportunities that money brings drive these types of investors. Know who they are, who they are friends with, how many companies they own, and what the track record of those companies is. Did they all seemingly swap the C-Suit around six months to one year after that investor got involved? This is either a red flag or an opportunity. Take your pick, and make sure you can live with it.

This strategy is another high-risk, high-reward strategy to take on in the tech industry. You might consider it if you're the best in your field and can save the day for an investor like this for some profit sharing. If you're not into doing that, be aware of it, and watch for the signs so you can get out with your severance package.

The Company I Quit is Likely A Prime Target for a 'Hostile Takeover'

I looked back on them, and they have, so far, fired 60% of their staff. They quite obviously ran out of money; if they didn't, they figured out their idea had a low profitability capability and shrunk. They (hopefully) learned a hard lesson. Data is a critical component of running a business. If you don't collect and use it, others will, and as a result, will clean-sweep your potential customers.

Would Hippy Take on That Project with the Investors? I would be full of shit if I said it wasn't an appealing option, I could easily turn a profit at that place, and the fact that the boss was a jerk makes it a reasonable option. My work ethic is nearly unmatched, and my ability to see the big picture is clear as a sunny day. I haven't decided yet, but I am leaning towards just doing what I'm doing now and avoiding the headaches instead. I prefer to be helpful on a bigger scale. The role I am in now lets me do that.

Know When You Should Quit

If you are in a situation like the one mentioned above, you should quit that job. They are too far out in the ether to understand anything you bring them. Data charts aren't going to help you here. It's a lost cause. Do your six-month contract, and don't renew it. Make at least one person on that team your ally, and make buddies with the investors. That way, you can still do some short-term work in a bind for cash if they have any left and keep your options open if the company starts hemorrhaging money.

They All Talk To Each Other

Think twice before you badmouth any company, product, developer, or leader in the industry. They all go to the same lunch spots.

Some of them deserve a good ego check, but guess what? That time your boss walked up to you out of nowhere and started fishing for your opinion on a product launch from another company? Here are four highly likely scenarios:

  1. They got asked to do it by their friend in the management at the other company.
  2. They wanted to see where your loyalty stood to the company.
  3. They wanted to see how your thought process works and if it would benefit them for an upcoming project.
  4. They were making small talk to see who you were.

Notice how the first option would be bad for you as a contractor or someone who may need to find work in the future due to the fickle nature of tech job stability? It's the first on the list because it's also the most likely scenario. It would be best if you did your research on your managers.

The Network Is Smaller Than You Think

Know who they are friends with, and see if there is overlap with managers at other companies. Did they go to the same college? Then that means they likely know each other on a friendly basis. Assume they are friends. It's the best approach to ensure you don't say something dumb. While employed by a company, or even just contracted with one, you introduce yourself to a much bigger audience than you think.

Good Managers Know Their Staff Well

Good managers know their people like the back of their hands. They know where they went to school, where they worked, their goals, and what drives them. You need to know the same about your boss. If they have a heightened ego, see if they earned it or just took the liberty of it. No golden handcuffs, no problem. Don't sign on for a w-2 without some good data.

Your Mental Well-being is Critical

Tech burnout is a real thing. Avoid it at all costs, even if you get canned for it.

Get a W-9 For Piece of Mind. They Need to Earn the W-2

Finally, it's worth considering the freedom gained from a w-9 over a w-2. The latter can quickly become "golden handcuffs," trapping you in a position even if the company becomes intolerable. As a contracted employee, you won't carry the stigma of the company on your resume. Instead, you'll showcase the project you worked on. It's essential to consider your long-term goals and choose your employment status accordingly.

Unrealistic Deadlines

Change them. Yep, it's that simple. They map out an impossible project, re-do it, and CC their boss on the email. They'll never do it again. Setting unrealistic expectations for the company's clients is a huge problem. It leads to lost contracts and bad reviews. You name it. If your boss decides you will do three weeks' worth of work in one week, correct it and return it, and CC their boss explaining why this project will take that time without an additional staff of (x) people.

As the section states, you might get canned for it, but this one is worth it. Besides, from the past contracts you've landed, you built relationships with plenty of people, and you weren't a jackass at the office, right? So finding another contract is easy for you now.

If you must avoid getting canned more than fixing your unrealistic deadlines, go GPT yourself a nice ATS resume, include all the cool projects you're building, and get away from that company. It's easier to get a job while you've got one.

Shut Off Communication When You Leave

It can wait. Not much else to be said here. This falls under managing expectations. I was terrible at this for years. I was a 'yes, it'll be ready tomorrow' kind of worker. Never again. I resented my manager and hated the work, likely because I was cranky. After all, I never slept. I took a month off of all technology after this particular role. No phone, computer, laptop, nothing. One month to recover. Now I make sure I put in the time to be a human. If I'm mentally drained, I take the day to finish mundane stuff so I'm not engrossed in a project. Don't use this as an excuse. You need to stay self-motivated regardless. Use it as a tool to rejuvenate, but don't abuse it.

That's the only time off I've taken in 15 years. That was nine years ago. I take days here and there, but no more than 2.

Grow a Plant

Grow a plant. Get a small kit, Bonzai, whatever. Just have one. It's a responsibility outside of your work and yourself. You have to keep it healthy, and it's not a keyboard. It'll get you away from the desk every once and a while. Pick one that smells good for a bonus.


I hope this helps a bit.

Be aware of all the stuff in your company if you decide to be in tech. It could save you from a surprise layoff or a terrible boss. Know who's who and who went to college together.

You'd be surprised at how small the tech world is. There are a lot of companies doing a lot of cool things to get involved with. You can be picky. Just be the best at what you do. If you're average or below average at what you do, you need to up those skills.

The onset of AI should be a top priority to fill in those shortcomings. Use it to teach you, fill in what you missed, and do what you gotta do. But if you're getting into tech now? You won't compete with anyone else if you don't leverage AI.

Now that's all said, with 15+ years in tech (actually closer to 20), I've found that the key is ensuring you have a good balance, ignoring mundane stuff, knowing who everyone is, and planning accordingly. If you decide to be a shark, it's not hard to do. Just be mindful that you're not making real friends that way. Make sure you get good.

You must put in the time to be the best at your work and make some investor friends. If you want a check and to be left alone, keep the w-9s on deck.

If you don't want to deal with that nonsense, don't do tech work, or go and start your own company. That's my thoughts on it.