Success No Matter What: How to Engineer a New Opportunity

By Nicholas McGill

Before starting a new venture, job, startup, relocation, investment, or big opportunity, steal one of Heroik’s operating mantras:

Success No Matter What.

SWIPE this - (Steal With Integrity and Pride Everyday). If something works, take the principle, understand it, adapt it, and make it your own. Chew the meat and spit out the bones.

“Success No Matter What” sounds motivational. It isn’t. It is a design constraint. It means you do not build a plan where only one narrow outcome counts as success.

You design the opportunity so that if Plan A works, you win.  If Plan A partially works, you still win. If Plan A goes completely sideways, you have already built enough options, assets, relationships, runway, and capability that you can turn the experience into the next move.

You cannot control everything that happens. You can control whether your original plan is the only way you come out ahead. The goal is not to predict the future correctly. The goal is to design enough optionality that being wrong about the future does not wreck you.

Success No Matter What is not an argument for playing it safe. It is an argument for taking bigger, better-engineered risks.

The objective is not to avoid getting hurt. The objective is to make bold moves while increasing the probability that the gains survive the move, even when the original plan does not.

You are not trying to preserve your current position forever. You are trying to level up, and keep as much of the level-up as possible.

Maximum sustained gain. Take the swing. Chase the upside. But engineer the bet so the skills, capital, relationships, access, reputation, experience, assets, and options you gain do not all disappear if Plan A does.

But how do you plan for it and make it happen? Start at as early as you can. At the beginning.

1. Get As Much Say In The Design As Possible

The more influence you have over the shape of the role, deal, responsibility, or engagement from the beginning, the better.

Do not assume an opportunity handed to you has been designed in your favor. It probably hasn’t. That does not mean anyone is trying to screw you. The organization offering the opportunity is simply doing what organizations do, designing around its own goals, risks, budgets, constraints, and incentives.

You should do the same. Your first responsibility is to make sure the opportunity strengthens your own position. That means preserving as much strategic autonomy as possible.

• What will you actually own?
• What decisions can you make?
• What budget can you control?
• What are you responsible for delivering?
• Will your title match your level of responsibility?
• Will you be able to build or hire?
• Will you have visible ownership over meaningful work?
• Can you speak publicly about what you build?
• Can you publish?
• Can you maintain outside professional activities?
• Can you retain ownership of your existing intellectual property?
• Can you preserve relationships outside the company?

Do not negotiate only salary. Negotiate the shape of the opportunity.

Sometimes the most valuable part of a role is not another $10,000 in compensation. It is authority, access, visible ownership, flexibility, title, budget, relationships, or the ability to point to meaningful work afterward and say:

I built that.

2. Straw Man it. Steel Man it. Red Team it. Then run the Pre-Mortem.

Most people examine opportunities emotionally. They get excited. They imagine the apartment, the title, the company, the city, the lifestyle, the upside. Then they unconsciously start defending the story they want to be true.

Don’t do that.

Use AI to grill you. Then use those reflections to discuss with smart friends. Use people who know you well enough to call bullshit.

Start with four passes.

Straw Man: What is the weakest realistic version of this opportunity?

Steel Man: What is the strongest realistic version of this opportunity?

Red Team: What are the flaws, dependencies, incentives, hidden costs, gaps, risks, and likely failure points?

Then run a Pre-Mortem. Imagine it is two years later and this decision was a disaster.

What happened?

• The company ran out of money.
• Leadership changed.
• Your boss disappeared.
• The role became administrative.
• The equity turned out to be worthless.
• The cost of living ate the salary increase.
• The relationship that motivated the move ended.
• You stopped learning.
• You became too dependent on one employer.
• You lost your network back home.
• You stopped building anything that belonged to you.
• You burned yourself out.
• You made a lot more money and somehow accumulated very little wealth.

Now work backwards.

• Which of those risks could have been detected beforehand?
• Which could have been negotiated around?
• Which could have been hedged?
• Which could have been insured against?
• Which are simply risks you knowingly accept?

This is not pessimism. This is engineering.

3. Red Team Staying Put Too: Comfort Has a Cost

When evaluating a big opportunity, people tend to put the risky option under a microscope and give the comfortable option a free pass.That is bad math.

Moving has risks. Taking the job, joining the startup or starting the business. But staying where you are has risks too.

There is no risk-free square on the board. The decision is not Risk versus no risk. It is one set of risks, costs, opportunities, and possible gains versus another.

So after you Pre-Mortem the big move, Pre-Mortem the decision to stay exactly where you are.

Imagine it is three years later and you did not take the swing.

What happened? Maybe nothing catastrophic happened. That can be the problem.

• You got comfortable.
• Your income moved sideways.
• Your network stayed roughly the same.
• Your responsibilities became familiar.
• Your learning curve flattened.
• The interesting people went somewhere else.
• The technology moved.
• The market changed.
• You accumulated another three years of experience, but not necessarily three years of growth.
• You stopped deliberately expanding your perimeter.

Meanwhile, the people who moved, built, failed, learned, met people, took calculated risks, and accumulated new capabilities started operating on a different board.

Comfort carries opportunity cost.

And over enough time, stagnation becomes its own form of concentration risk.

• Your choices narrow.
• Your skills become more specific to the environment you already occupy.
• Your network grows inward instead of outward.
• Your compensation becomes dependent on fewer viable alternatives.
• Your tolerance for change decreases because the cost of changing gets psychologically and materially larger.

Eventually, necessity starts making decisions that courage should have made years earlier.

That is the danger.

Do not merely ask: What could I lose if I go?

Also ask: What could I lose by staying?

• What will another two years here do to my earning power?
• What skills will I fail to acquire?
• What relationships will I never develop?
• What rooms will I never enter?
• What experiences will I miss?
• What opportunities will become harder to pursue later?
• What happens if my current role, employer, industry, or geography deteriorates while I remain comfortable?
• Am I preserving optionality, or quietly consuming it?
• Is staying strengthening my position, or merely postponing a decision?

The comfortable option should have to survive the same scrutiny as the bold one.

Sometimes staying wins. Great.

But make it win the argument. Do not award it the decision by default just because it requires less courage today.

Robust Risk-Taking

The goal is not reckless risk. It is not safety either. The goal is robust risk-taking.

Take the home-run swing while building Moneyball plays underneath it.

Build multiple ways to win. Build multiple positive exits. Map the adjacencies. Know what else the move can produce if the headline outcome changes.

If the new venture works, fantastic.

If it does not, perhaps you leave with two years of extraordinary relationships, a stronger reputation, a valuable specialty, cash in the bank, a body of work, another offer, and knowledge that puts you three moves ahead somewhere else.

That is not failure. That is a swing with multiple positive exit points. Those are still wins. That is still a success.

Take risks that can level you up in more than one way.

Then work to keep the gains.

4. Evaluate the Whole (Holistic) Opportunity

Heroik’s approach to engineering an opportunity is in a word; Thrivalism; AKA Success No Matter What.

You have limited amounts of control, influence, and reconcile that with your responsibility to provide abundantly on top of that.

Your first priority is to create a win-win. Your second priority is to make sure your win is even bigger for you, from your perspective.

This doesn’t mean getting greedy or taking more from the deal just for the sake of taking more. It means optimizing it for YOU and YOUR goals.

Secure enough value that, if the other side could completely see the opportunity from your perspective, they might reconsider just how good a deal you got.

That bigger win does not have to mean more money. It could mean less risk, less liability, less responsibility, more freedom, more access, better upside, or a cleaner exit, or a better way to apply and leverage the opportunity into the rest of your life.

The opportunity is not the whole board. Your life is the whole board. See the whole board.

You need to properly assess the value of the opportunity, and the risk-to-reward ratios need to line up FOR YOU, from your perspective.

See The Whole Board On Real Terms Of Today’s Economy

These days, most people have an outdated economic model in their heads.

Example: People think that earning $240k a year is a lot. In reality, $240k per year is the new $89k from the 90’s (price point reference for most people). That’s the upper-end top 12% of middle class - you used to be able to get with $89k in joint income. That gets you a decent living, house, car, maybe pool and or boat and hobbies you can afford to neglect.

It disappears in today’s economy, and most people’s mental model for economics is lagging greatly behind inflation (ESPECIALLY the under-reported impacts of BIDEN-FLATION). This is particularly relevant because the under-reported impacts of those years, mean that the rest of society has a misinformed perception of economics.

You can’t afford to operate on Covid/Biden pre-inflationary economics. It is in the buyer’s benefit, to have you operate on an outdated economic model. This ensures you settle for less.

Do not negotiate against the economy you or they remember. Negotiate against the economy you all actually have to live in.

Calculate The Real Value Of The Opportunity

Scan the environment - including the overall state of the economy and job market (who has leverage, employer, or employee),  cost of living, taxes, the works. It adds up in a hurry.

A salary is not the value of an opportunity. It is one line item.

People regularly make life-changing decisions because a large nominal number triggers an emotional response. Then they discover they did not actually improve their lives very much. You need to calculate the opportunity in real terms.

Start with the obvious financial pieces:

• Salary
• Bonus
• Equity
• Retirement contributions
• Healthcare
• Relocation assistance
• Severance
• Professional development
• Travel
• Other benefits

Then subtract the real costs:

• Federal, state, and local taxes
• Housing
• Transportation
• Insurance
• Interest rates
• Debt servicing
• Relocation expenses
• Lifestyle inflation (pressure to keep up w the Jones’ is real)
• Opportunity cost

Adjust for the operating region if you’re relocating:

Example: $60K in Knoxville Tennessee operates differently than $160k in San Francisco or Manhattan. On paper it looks like an upgrade, but if you don’t have a plan, it slips through your fingers and you’re actually worse off on dollar terms alone.

You don’t move across the country and relocate - surrender everything for $60k to $160k - unless there’s a lot more potential upside to the rest of that equation. Do the math, interest rates, cost of living, etc. Unless you’re an ex-con, or total hermit in your current community,  there’s no way the odds will out in your favor for that.

But even that is incomplete.

At Heroik, we use another capacity measure:

TEA: Time, Energy, Attention.

Where are you pouring your TEA?

A $300,000 job that consumes your evenings, weekends, health, relationships, mental bandwidth, commute time, and ability to explore may be a worse deal than a $220,000 role that preserves enormous discretionary capacity.

Time is scarce. Energy is renewable, but exhaustible. Attention determines whether your time and energy are pointed toward anything useful.

You need to know what the job pays. You also need to know what the job costs.

Where are you pouring your TEA?

5. Get Into The Bug Guts (The Finer Things) - What is the Deal Really?

Now look beyond compensation. Ask what the opportunity makes you more valuable at. A good opportunity should increase several forms of capital at once.

Financial Capital - What can you actually save and invest?

Capability - What will you know how to do afterward that you cannot do now?

Reputation - Who will know you are good?

Access - What rooms become easier to enter?

Relationships - Who will you genuinely know?

Proof of Work - What can you point to?

Forward Signal - What will you see earlier than people outside the environment?

Future Earning Power - Does this meaningfully raise the value of your next move?

Autonomy - Will this leave you with more control over your future choices or less?

This matters enormously when considering a place like San Francisco. Do not evaluate San Francisco only as a place to live or a salary to earn. Evaluate it as an ecosystem you may be buying temporary access to.

Being physically close to founders, investors, engineers, researchers, technology companies, operators, universities, and commercialization networks can have tremendous value.

But only if you actually acquire the access. Living near interesting people is not the same as knowing them. Working in an innovation ecosystem is not the same as developing standing inside it.

So ask:

• Who will I actually work beside?
• Who will take my call after two years?
• Whose problems will I understand?
• What communities will I earn standing inside?
• What information will reach me earlier?
• What doors become easier to open?
• What people will know enough about my work to recommend me?

Sometimes accepting slightly worse immediate economics is rational if you are purchasing extraordinary access, experience, forward signal, and future earning power.

Just make sure you are intentionally making that trade.

6. Understand The Shelf Life Of What You Are Learning & Working On

This is becoming increasingly important. The half-life of technical advantage is shrinking.

A tool that makes you unusually valuable today may be normal, automated, cheap, or irrelevant two years from now.

So do not merely ask:

What will I learn?

Ask:

How long will what I learn remain valuable?

At Heroik, we think about three kinds of shelf life.

Technical Shelf Life:

How long will this specific skill, tool, technology, or technique remain relevant?

Strategic Shelf Life:

How long will knowing it actually differentiate me?

Operational Shelf Life:

How long can I personally continue extracting value from it before my advantage decays?

Learn current tools. Know the vocabulary. Understand the platforms. But go deep on principles.

If you spend several years learning the current AI tooling, that knowledge may decay quickly. If you spend several years learning how technology commercialization works, how innovation ecosystems form, how capital moves, how institutions adopt technology, how leaders make innovation decisions, how partnerships are built, and how organizations navigate technological disruption, those principles have a much longer shelf life.

Do not merely become good at today's thing. Become better at understanding why things work.

7. Always Pack A Parachute

This has many layers.

The best time to build a parachute is before you need one.

In every engagement, project, job, adventure or misadventure there is almost always:

• A story to tell and data to sell
• Relationships to preserve and leverage
• A reputation to build.
• Proof of work to capture.
• Capital to save.
• Capability to accumulate.

Before you start the opportunity, ask yourself:

• If this goes to shit, what story will I be able to tell about what I did and learned?
• What must I document along the way so that story is credible later (in case you need it)?
• What data can I legally and ethically retain?
• What adjacent data can you gather along the way (beyond the scope of interest of the engagement)? (Like picking flowers on a hike, making a nice bouquet for someone).
• What information or first-party data can I gather or create that I am entitled to use later?
• Who should I invest in knowing?
• What adjacent industries, opportunities, or relationships might emerge from this environment? (Being aware of adjacencies can save and change your life).
• What work should I make sure I can point to?
• Who needs to know I was responsible for it?
• What should my reputation be when I leave?

A great opportunity should leave lasting artifacts.

You should walk away with more than memories and direct deposits. The experience should leave behind assets you can point to, carry forward, compound, or convert into the next opportunity.

8. Create A PACE Plan

PACE comes from military communications planning:

Primary. Alternate. Contingency. Emergency.

It is a simple way to prevent yourself from mentally treating one plan as inevitable.

PACE is not merely a ladder of “disaster” planning. Used properly, it is a way to design multiple acceptable outcomes before making the move.

Your Alternate should not be "what happens when I lose."

Your Contingency should not automatically mean retreat.

Whenever possible, they should be different ways to keep moving forward.

If Primary is the home run, Alternate may be the double. Contingency may be getting on base, preserving capital, and stepping into the next at-bat with a stronger position than you started with. Only Emergency is truly about stabilization.

Design positive exits before you need an exit.

Primary Plan

The Primary Plan is the dream scenario.The company is great. The role is great. The relationship is great. The money is great. You grow. You build. You develop significant access. Everything more or less works.

Fantastic.

As Hannibal Smith would say:

“I love it when a plan comes together.”

Unfortunately, life regularly introduces John McClane economics:

“Come out to the coast, we’ll get together, have a few laughs.”

Sometimes the trip to the coast gets complicated.

Alternate Plan

Your Alternate Plan should still be attractive. If Primary Plan A = I’m getting this great job in Silicon Valley that pays $300k, the Alternate plan is I’m taking this okay job in Silicon Valley for $180k.

Here’s the rub - An Alternate Plan is only real if you have done the work required to preserve it.

In this case, for the Alternate Plan to be viable, you need the offer for the other job to exist. This means you need to be interviewing for the “okay job”, even if you’ve already been promised the job that fits your Primary plan. A bird in the hand is worth two in the bush.

The guidance here: pursue and secure multiple adjacent offers (same sector, region, industry), keep them open until you’re up and running.

Questions to ask to maintain a viable alternate plan:

• What is required to preserve this as a viable plan?
  • Maintaining your LinkedIn presence.
  • Maintaining your personal website - The full expression of yourself, portfolio and endeavors on your own terms, NOT AN ALGORITHM’s terms.
  • Maintaining professional relationships. You still make time to network, build MEANINGFUL relationships and connections, and budgeting to serve others in clever and generous ways.
  • Staying current.
  • Taking calls.
  • Knowing what companies are hiring.
  • Knowing who has money.
  • Knowing who is building.

A parachute you forgot to pack is not a parachute.

Contingency Plan

The Contingency Plan is less ideal, but still solid ground, still workable. Maybe the company fails. Maybe the market changes. Maybe the role is not what you were sold. Maybe personal circumstances change.

Your Contingency Plan might be to get a stable job with benefits (healthcare and a 401k),  that’s less demanding, that allows you to hedge with a side hustle. This could be a state, county, university, healthcare or nonprofit job, or something else between - and YES I am poking fun at those industries.

It may mean returning geographically. It may mean changing sectors. It may mean using your accumulated relationships and reputation to land something entirely different.

Beyond the job change, your Contingency Plan may be to cash in on what you developed and cultivated - that data to sell, story to tell and relationships to leverage. Time to cash in on those.

Emergency Plan

The Emergency Plan is the final stable option. Its purpose is not to preserve prestige. Its purpose is to cover your nut and buy thinking time.

You need enough money coming in to stop the bleeding while preserving enough TEA (Time, Energy, and Attention) to regroup, think, decide, and execute the next plan.

A good Emergency Plan might be:

“My friend Paul works construction and is always hiring guys - I can do that and buy myself a runway, and time to think about next moves, regroup and execute.”

That is dramatically different from having no plan and suddenly improvising survival.

Working at Starbucks, Using credit cards, taking out a home equity Loans, Uber, DoorDash, Cleaning Gutters, Pressure Washing Driveways or Trash Cans, Buy/Sell ebay or Facebook Marketplace, crashing at your buddy’s place, etc.

Those are not Emergency Plans. Those are sustenance tactics, Naked and Afraid shit. Know the difference. Your Emergency Plan should put you back on solid ground, not merely keep you alive another day.

9. Reduce Concentration Risk

Most employees have an enormous concentration problem. One employer controls all of their income. Often the employer also controls their title, identity, access, healthcare, daily relationships, and professional visibility.

That works wonderfully until it doesn't.

Do not disappear inside your employer. Build an identity bigger than your employee badge.

• Maintain your professional relationships.
• Maintain your personal domain.
• Maintain your personal email address.
• Maintain a body of work.

Everyone should have ABBS (Always Be Building Shit)- outside of the box, beyond the confines of the current engagement. ABBS is how you keep some portion of your capability, identity, and productive momentum outside the walls of whoever currently signs your paycheck. Keep writing. Keep learning. Keep showing up in your professional community. This does not mean living with one foot out the door. It means refusing to surrender your sovereignty.

Maintain your relationships in your hometown. Build new relationships in the new town.  Keep enough awareness of the market to know where the exits are.

Pro-tip: Have AI and your calendar create auto reminders to check in with key contacts and relationships. These should be reminders to send personal messages that amount to asking “What’s up? How are you doing?” and respond and share in kind based on the response. This is not a license to create robotic slop comms with key contacts. Automate the reminder, not the relationship. The message should still come from you.

The employer/provider owns the job/opportunity. They should not own your professional existence. NEVER ever surrender that.

GUARDRAIL - NEVER allow yourself to get so lost in the job you neglect the rest of your professional existence.

10. Make The Opportunity Compound

There are broadly two types of work. Some work pays once. Other work pays you while also building assets that keep paying later.

The first is mercenary. The second compounds.

A job is necessarily partly mercenary. You trade a portion of your life for compensation. But the best career moves also compound.

Ideally, they leave you with:

• Better relationships.
• Better reputation.
• Better judgment.
• Better capabilities.
• Better access.
• Better stories.
• Better credentials.
• Better future choices.
• Higher earning power.
• Perhaps equity.
• Perhaps investments.
• Perhaps intellectual property developed outside the employer.
• Perhaps a business idea.
• Perhaps relationships that produce opportunities for twenty years.

Some of those things compound in value and impact on your life, if you steward and protect them. But beware, There is a catch: not all compounding assets are equally yours.

Some of the things that appear to be yours are actually granted by other people or institutions.

Your title can disappear. Your access can disappear. Your credentials can lose value. Your reputation can be damaged or reinterpreted. Relationships can cool, get blocked, or become politically expensive. A company can reorganize, change leadership, remove your visibility, cut off your access to key people, or simply stop validating your role in the story. And often, the employer is the choke point through which several of those assets flow at once. That’s concentration risk right there.

That means you should absolutely build relationships, reputation, access, credentials, and standing, because they matter enormously. But do not confuse valuable with fully owned. The more dependent an asset is on someone else continuing to grant, recognize, validate, or permit it, the less control you actually have over it.

So build compounding assets across different levels of control.

Build the externally granted assets: relationships, reputation, access, credentials, title, and institutional standing. Don’t over-value them or mis-read their fragility.

But also build the things that are much harder for anyone to take away:

Judgment, principles, frameworks, processes, skills, documented experience, savings, investments, portable proof of work, and intellectual property you legally own.

Own some of the machinery beneath the outcome. The work behind the work.The operating principles that make the results possible. Those are gold.

You want to leave an opportunity with more than borrowed status. You want assets that still exist after the badge stops working.

The question is not simply:

What am I getting paid?

It is:

What am I becoming while I am getting paid?

That is a much more important question.

There is another question underneath it:

How much of what I am becoming do I get to keep?

This is the difference between temporary upside and sustained gain.

• A promotion you lose when the company collapses was useful.
• The judgment you developed while earning it is portable.
• Access granted through an employer can disappear.
• The ability to create access for yourself is much harder to take away.
• A large paycheck ends when the job ends.
• The assets you purchased with the surplus can keep working.
• A prestigious title may vanish.

The proof that you can actually perform at that altitude can follow you.

The goal is to convert as much temporary opportunity as possible into permanent or durable expansion.

Those are the level-ups you keep.

11. Convert Temporary Income Into Permanent Optionality

If you take a lucrative opportunity, do not immediately translate the income into a more expensive lifestyle.

That is one of the easiest traps in the world.

• The expensive apartment.
• The new car.
• The restaurants.
• The wardrobe.
• The subscriptions.
• The premium everything.

Suddenly you need the job. You make dramatically more money and somehow require dramatically more money just to keep your life standing upright.

That is not progress. That is a more expensive dependency. That is the opposite of what the money was supposed to accomplish.

So for the first six months especially, live beneath your means. Aggressively.

Save like a motherfucker.

Aggressively. Build runway. Kill bad debt. Fund retirement. Accumulate assets.

Think about real estate when appropriate. Invest. Preserve liquidity.

A larger paycheck should create freedom, not merely finance a more elaborate cage.

If you have a fitness mentality, develop a financial fitness mentality.

You do not become fit from one workout. You become fit because disciplined choices become your normal operating pattern.

Money works the same way. Frugality is not about deprivation. It is about optionality. Every dollar you do not permanently attach to your lifestyle gives Future You more room to maneuver.

Buddy, pay attention - I wish I learned this sooner.

Start turning temporary income into permanent optionality. This took me years to really submit to. I wish I had understood it twenty years earlier. Learn from my scars and mistakes brother.

Financial fitness shows up in stupid little decisions all day long.

Simple Example - Practical - The gas station can sell you a perfectly decent XL latte for $2.19 while Starbucks can turn the same basic act into an eight-dollar event. If the cup matters that much to you, buy the reusable Starbucks cup and fill it somewhere cheaper.

The principle is not coffee. The principle is refusing to let vanity taxes chew holes in your parachute, or eat the seed funds of your future, levelled-up life.

Costco is your friend. Gas. Groceries. Clothes. Hot dogs. Date night. Household stuff. Program an AI agent to stalk deals for you. Know when to buy what. Take pride in this.

Learn to extract value from systems instead of paying retail because it is convenient or because someone successfully convinced you that paying more means you are doing better. Let somebody else eat depreciation.

• A one-year-old Mac in great condition still does the work.
• A two-year-old vehicle still gets you there.
• A used kayak still floats.
• A used gaming console still wastes exactly the same number of hours.

The fish do not care whether your kayak had a previous owner.

Remember, the first guy through the wall gets bloody. Not the second.

The second mouse gets the cheese.

These serve as lessons for many things. One of them - the first buyer pays for the privilege of removing the plastic. You can often buy the same utility after someone else has already absorbed the steepest part of the loss.

I used to be a bleeding-edge guy with everything. Now I am perfectly happy waiting for the new model to come out so I can buy the old one from somebody who suddenly cannot stand looking at it anymore.

Let them eat Apple’s profit margin. You still get to vibe code on a nice Mac. You just keep more of your money.

The same goes for professional clothing.

Buy quality. Look sharp. But buy stuff you can actually maintain. If a shirt costs twenty bucks every time you dryclean it, eventually you have bought the shirt again just trying to keep it clean.

They make suits and professional clothing you can wash, steam, travel with, and keep looking good without building a recurring maintenance contract with the dry cleaner.

Do not let some idiot flex on you with Tom Ford while you are still trying to build your first real balance sheet. Shopping Tom Ford suits is third-house shit. Build the first balance sheet first.

Your first job is to build strength. And this is the real principle underneath all of it:

Financial fitness means your lifestyle grows slower than your income, so your assets, investments, and options can grow faster. The object is not merely to experience the higher income. It is to convert a temporary income level into a permanently stronger financial position.

When your income jumps, there should be a gap. That gap is where freedom gets built. Use the surplus as SEED money.

It becomes cash. Investments. Retirement. A down payment. Real estate. A business opportunity. Thinking time. The ability to walk away from a bad deal. The ability to survive getting fired. The ability to make a bold move without asking a bank or credit card company for permission.

That is what savings actually buy - Options. And options are the whole point of the parachute.

Every dollar you permanently attach to your lifestyle becomes another dollar spent that Future You has to earn before he can make a free decision. Every dollar you preserve gives future you more room to maneuver.

So enjoy the upside. Celebrate the win. Go out to dinner. Buy something stupid once in a while. You are allowed to live.

But do not celebrate finally making serious money by immediately designing a life that makes you terrified to lose the job.

That defeats the entire purpose. The job should make you freer. Not more expensive. Take it from an old man with scars and receipts to show for it.

You made $300K for three years? Great. What remains when the $300K stops?

If the answer is a larger mortgage, expensive habits, and a leased Porsche, you experienced an upside, but might not be able to hold it. If the answer is retirement funding, investments, a down payment, six months of runway, reduced debt, and freedom to make the next move, you kept the level-up.

12. Put A Review Date On The Decision

Do not make a permanent emotional commitment to what should be an experiment.

You can move to San Francisco without deciding that you must live there forever.

Define the decision horizon.

• What does success look like after 12 months?
• What should you have learned?
• Who should you know?
• What should you have saved?
• What should you have built?
• What should your reputation look like?
• What options should now exist that did not exist before?

Then do it again at 24 months. And 36.

Re-underwrite the bet.

• Do not stay because you moved.
• Do not stay because you already invested two years.
• Do not let sunk cost become destiny.

One of our other Heroik principles is:

Live It or Leave It.

Cultivate that which serves you.And unapologetically hit the eject button on that which does not. No guilt. No shame. New choices.

It is critical to know your EJECT criteria well in advance. Train for it.

If the company or opportunity value starts to dip by X% of your initial assessment (quantitative and qualitative). Have internal checkpoints and predetermined warning thresholds. Don't invent your standards while the airplane is already falling.

Example triggers might include:

• Compensation materially changing
• Equity being diluted beyond your original thesis,
• Repeated leadership turnover
• Authority being removed while responsibility remains
• The role drifting materially from what was sold
• Runway falling below a predetermined threshold
• Your health deteriorating
• Your relationship or family paying an unacceptable price
• Learning and access flattening
• The opportunity consuming substantially more TEA than originally budgeted

Decide which are warning lights, which require corrective action, and which are ejection handles.

Terrain. Terrain. Terrain. Pull Up. Pull Up. Pull Up.

You should never be this low to the ground in the first place. More than one thing is going on if you’re experiencing and perceiving this kind of message. The risk-to-reward ratio better be egregiously in your favor to warrant hugging the ground.

Canopy. Canopy. Canopy. Eject. Eject. Eject. Know your number. Know the conditions.

What are the triggers that make you push the Eject button?

Know them in advance so you don’t second guess yourself when the moment counts.

Here’s a harsh reality: The story of your career, and upward trajectory is tied to your fruits and outcomes. If you’re on a bad ship that’s going nowhere fast, or sinking slowly.

Do not anchor yourself to bad leadership, management, business model outcomes that you know are bad and cannot change without herculean effort beyond the scope of risk/reward ratio. MOST businesses fail. Many more suck from a model, leadership and management position.

Your job is Success No Matter What - for you - do not conflate that with the responsibility to make the bigger model succeed, for everyone, no matter what.

People will try to bait you to stay in and ride it out. Assess the risk/reward, and weigh it against the greater responsibility to provide and advance yourself.

I have learned this the fun way. I was an over-committer - and would ride engagements supporting leadership, management and champions, into the ground. This hindered my progress and development as well as financial outcomes, resume, and so on. There’s a graveyard of ventures and gigs and startups I’ve seen come and go - I would have done better to pull out and move on to better opportunities.

Loyalty is a virtue. Martyring your own trajectory for somebody else's broken model is not. Learn the difference.

The Goal Is Not Certainty

You will never completely eliminate risk from a big opportunity. Nor should you.

The objective is not building a perfectly safe life. The objective is becoming harder to trap, and increasingly capable of operating expansively.

And this is where people can misunderstand the entire framework.

Becoming harder to trap does not mean becoming harder to move.

The whole reason to build the parachute is so you can jump.

The whole reason to build runway is so you can take off.

The whole reason to preserve options is so you can exercise them.

Safety is not the primary objective. Expansion is.

But we want expansion that holds. We want gains we can keep. We want the move to leave us stronger regardless of which route through it ultimately becomes real.

• Build enough capability that you can work → EXPANSIVELY.
• Enough relationships that you can reach the right people,→ EXPANSIVELY.
• Enough reputation that people will reach you →EXPANSIVELY.
• Enough capital that you can afford to think →EXPANSIVELY.
• Enough discipline that you do not consume your own runway, but use it carefully and strategically to seed and water your life →EXPANSIVELY.
• Enough awareness to recognize when the terrain changes. Keep an eye on the horizon. Environmental scans (periscope reads) are critical.
• Enough courage to make the moves →EXPANSIVELY.
• Enough humility to change course when the evidence says you should →EXPANSIVELY.

A successful opportunity should increase the number and quality of choices available to you afterward. If your choices are narrowing while your paycheck is growing, pay attention.

Then you do not need Plan A to be perfect. Plan A may work spectacularly. It may merely work for a while. It may introduce you to Plan B. It may blow up and become the best story you ever tell. The important part is that you designed the opportunity so there are multiple paths to victory.

That is what Success No Matter What actually means.

Bottom-line: Take robust risks. Pursue asymmetric upside. Engineer multiple ways to win. Convert temporary upside into durable assets. Keep the level-ups. Then take the next swing from higher ground.