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Should I Sell My Company Stocks?

Among several discussions on the Internet, I came across a few common questions such as:

“Should I sell my company stock options?”

“Can I sell my company shares to anyone?”

“When should I sell my company stock?”

“How much should I sell my stock for?”

Today, I will shed some light on the following aspects so that you can have clarity on whether should you sell your company stock and when should you sell your company stock.

The compensation for an employee comprises several components like basic pay, social security contribution, allowances, bonuses, etc.

Some companies, however, offer compensation in the form of their stock.

Usually, stock compensation offered to employees is of multiple types, which include:

  • Stock Options
  • Restricted Stock Units (RSUs)
  • Employee Stock Purchase Plans (ESPPs)
  • Stock Appreciation Rights (SARs)
  • Performance Shares
  • Employee Stock Ownership Plans (ESOPs)
  • Phantom Stock
  • Employee Stock Grants

Let us have a look at each of these individually to have a better understanding of stock compensation to employees.

If you want to invest as an expat or high-net-worth individual, you can email me (advice@adamfayed.com) or use these contact options.

Stock Options

Understanding employer stock options is essential.

In short, they let you buy company shares at a fixed price, usually lower than the current market value.

This overview covers the basics of stock options, how they work, and how to estimate their value.

Given the recent increase in initial public offerings (IPOs), employees must know how stock options function.

Especially, if their company is going public or intending to go public.

Stock options are a common type of compensation, granting the right to buy a set number of shares at a fixed price over a specific period.

Stock options are incentives for new hires, allowing them to get company stock at a discount.

Vesting ensures employees stay to take ownership of the options granted.

Exercising stock options depends on vesting, which typically expires 5 to 10 years after being granted.

Various methods exist for exercising options, and evaluating their worth involves considering the current stock value, strike price, and potential market changes.

Tax implications differ for Incentive Stock Options (ISOs) and Non-Qualified Stock Options (NSOs).

NSOs trigger ordinary income upon exercise, while ISOs may lead to Alternative Minimum Tax (AMT) if held past year-end.

These tax implications may differ based on the country and tax regulations.

The timing of selling shares determines whether they are taxed as long-term or short-term capital gains.

Navigating stock options requires understanding their value and integrating them into a diversified portfolio.

Due to the speculative nature of stock options, collaboration with financial advisors or professionals is advisable for strategic evaluation.

Restricted Stock Units (RSUs)

RSUs are like a gift of company stocks given to new or valued employees to motivate and reward them.

They’re part of the compensation package, especially popular in startups and tech companies.

When you get RSUs, you decide to accept or decline them.

After a waiting period (usually a few years), you receive either company stock or cash. This depends on certain conditions set by the company.

RSUs help attract and keep talented employees and they’re a way to compensate employees without immediate costs.

The value of company stock isn’t always predictable and RSUs may not always be enough to get the right people.

The exact value of RSUs isn’t known until shares are given.

RSUs make employees part owners of the company, and after the waiting period, you get the shares at their current value.

You might make more money if the company does well. The actual value of the stock may not meet expectations and it often takes a few years to get all the RSUs.

Imagine you get 600 RSUs as part of a job offer. If the company does well, you can make money when you get these shares.

But if you leave before a few years, you might not get all of them. RSUs may have rules about when you can get them. It could be based on time (a few years) or achieving specific goals.

Sometimes, it’s a mix of both.

After waiting for a few years, you can sell the shares to make a profit. However, holding onto them may not always be a good idea, especially if the stock price doesn’t go up.

You usually pay taxes when you get the RSUs. The amount you pay depends on the value of the shares at that time.

Tax rules can be a bit complicated, so it’s good to talk to someone who understands taxes in your country.

RSUs can be a good way for companies to attract and keep talented employees, but it’s essential to think about the costs and benefits for both the company and the employees.

Employee Stock Purchase Plans (ESPPs)

An Employee Stock Purchase Plan (ESPP) lets employees buy company stock at a discounted price through payroll deductions.

There are two types: qualified and non-qualified plans.

The process involves choosing to enroll, starting payroll deductions, extending the offering period, purchasing stocks, and complying with eligibility criteria.

Deductions are limited to $25,000 yearly.

Taxation is complex, with original stock discounts taxed as ordinary income and capital gains as long-term if certain conditions are met.

Participating in an ESPP has benefits like:

  • Discounted stock prices
  • A straightforward enrollment process
  • Aligning employee and shareholder interests
  • Boosting employee effort and morale

However, there are potential downsides, including decreased morale if share prices fall, compliance challenges, and administrative burdens for plan management.

Stock Appreciation Rights (SARs)

A Stock Appreciation Right (SAR) is a compensation right tied to a company’s stock price increase.

This provides employees with cash payments equivalent to the stock appreciation without requiring them to purchase the stock.

SAR programs allow companies to structure compensation schemes based on individual needs.

Tandem SARs, combined with stock options, assist employees in funding option purchases.

SARs motivate employees by tying them to performance objectives set by the company, providing an incentive for their efforts.

Transferable and subject to a clawback policy, SARs allow companies to recover incentives under specific circumstances, such as an employee switching to a competitor.

Settlement dates are flexible, and linked to the company’s objectives like profits or sales targets.

In a practical example, if ABC Limited granted SARs at $10 per share with a vesting date share price of $90, an employee awarded 100 shares would have an in-money value of $8,000.

Tax treatment is similar to non-qualified stock options, with employers handling withholding tax responsibilities.

SAR plans offer advantages, including:

  • Cash benefits without upfront costs
  • Flexibility in tailoring plans
  • Motivation tied to company performance

However, tandem SARs may impact a company’s shares by increasing outstanding shares.

SARs and phantom stocks share similarities, with phantom stocks entitling employees to cash payments equivalent to stock price increases.

Both are subject to similar tax treatment as ordinary income.

Performance Shares

Performance shares are a common incentive offered by companies to reward employees for good performance and align their interests with shareholders.

This initiative is a win-win situation when the company performs well.

It encourages employees to work towards the company’s long-term success, improving retention and overall business performance.

A Performance Stock Unit (PSU) is a form of equity compensation given to employees based on the company’s success over a specified period.

Companies use PSUs as a means to incentivize and retain their staff.

Employees benefit from the company’s success through the allocation of shares, subject to vesting rules.

Key features of performance shares include performance-based vesting, where shares vest based on achieving specific performance targets.

This focus on long-term goals aligns employees with the company’s success, fostering motivation and commitment.

Performance shares also serve as a retention tool, as they typically vest over several years.

Employees should be aware of the tax implications of performance shares.

This is because they may be taxed differently than other equity compensation types.

In the long run, performance shares connect the stock’s value to the company’s performance, providing employees with potential long-term financial rewards as the company succeeds.

Should I Sell My Company Stocks

Employee Stock Ownership Plans (ESOPs)

An Employee Stock Ownership Plan (ESOP) is a company benefit that gives employees ownership through stock shares, allocated without upfront costs.

These shares are held in a trust until employees retire or leave, aligning their interests with shareholders.

ESOPs encourage long-term commitment, improve retention, and motivate employees to focus on the company’s success.

To implement an ESOP, a company creates a trust, contributing new stock shares or cash to buy existing shares, with tax-deductible benefits.

Allocation is based on compensation or years of service, and vesting is required before employees receive shares.

ESOPs offer tax benefits, with no tax on contributions, and taxation only upon distribution.

This structure boosts employee engagement, positively impacting sales growth and employment.

However, ESOPs have drawbacks. Lack of diversification concentrates savings in one company, posing risks if it fails.

Newer employees may have limited benefits compared to longstanding ones.

Share ownership can be dilutive, reducing ownership percentages and voting power as more employees join the plan.

Phantom Stock

Phantom shares are an arrangement between employees and employers in a phantom stock plan.

These allow participants to receive cash payments based on the market value of company shares at specific times or conditions.

There are two main types of phantom stock plans: “Appreciation Only” and “Full Value.”

In the former, participants get cash equal to the difference between stock prices at redemption and the phantom stock’s issuing price.

In the latter, participants receive cash equal to the value of the underlying asset (common stock) at redemption.

Unlike stock options, where participants receive common stock, phantom stock plans offer cash payments upon redemption, avoiding shareholder dilution.

The issuing price of phantom shares is set by the company, not necessarily tied to the current stock value.

Considerations include ensuring the company’s stock price at redemption exceeds the issuing price for participants to benefit.

However, these plans can pose an uncapped liability for companies, as payments are linked to share prices at redemption.

Companies may mitigate this by setting a higher issuing price or capping cash payments per phantom stock.

Employee Stock Grants

A stock grant is when a company gives its employees shares of its stock as a form of compensation for their services.

This aims to keep them motivated and invested in the company’s success.

These grants often come with restrictions, like a vesting period, meaning employees only receive the stocks if they stay with the company for a set time.

Stock grants differ from stock options, where employees have the right to purchase stock at a predetermined price.

The goal of both practices is to motivate employees by linking their efforts to the company’s success.

There is no need for an immediate cash payment from the employer.

Companies issuing stock grants need formal agreements specifying details such as the number of stocks granted and the vesting schedule.

Employees review and accept these agreements, signaling their agreement by signing and returning them.

In terms of taxation, employees owe income tax on stock grants, but this tax is deferred until the stocks vest.

Employers issuing stock grants may qualify for a corporate tax deduction, with reporting requirements on IRS forms.

Extending stock grants to foreign employees is possible.

However, it’s essential to check local laws for any restrictions and consider the varying tax implications in different locations.

Now, let us get to the spotlight section of our topic for today, which revolves around whether or not you should sell your company stock.

Related Content:

Are Employee Stock Options a Good Investment?

The Downsides of Employee Stock Options

What to Do with Employee Stock Options?

Should I Sell My Company Stock?

selling company stocks

For individuals with equity compensation like stock options, deciding when and how to exercise those options can be a significant consideration.

That’s why most people often think about “Should I sell my company stock options?”, “When should I sell my company stock?”, etc.

A common dilemma is whether to sell the acquired shares immediately for cash or to hold onto them with the expectation of appreciation.

The question of whether to sell stock is often asked by clients with stock options, presenting a choice between:

  • Obtaining immediate cash, which can be used for various financial goals.
  • Holding onto the shares in anticipation of potential future growth.

The decision may hinge on one’s confidence in the company’s future success.

To make an informed decision, it’s crucial to consider specific factors related to your non-qualified stock options.

Begin by clarifying your primary objectives and understanding how these assets fit into your overall financial plan.

Your Perception

Your perception plays a key role in deciding whether or not should you sell your company stock.

Identify whether your immediate concern is funding short- to mid-term projects or achieving long-term financial goals.

Another essential aspect is how you perceive your company shares, i.e., as a source of fast cash or as long-term assets with growth potential.

Some individuals may opt for immediate cash by selling their stock promptly.

While others may see the stock as part of a larger investment strategy, holding onto it for potential future returns.

Ultimately, the decision regarding selling or holding company stock depends on your financial priorities, goals, and your confidence in the company’s future performance.

What Do You Think of Your Company’s Future?

In terms of financial planning, it’s generally advised to steer clear of emotional decision-making, particularly in the context of investment decisions.

Emotional impulses can potentially derail a well-thought-out plan and strategy, leading to significant and costly errors.

Nevertheless, financial decisions are not made in isolation.

Attempting to predict a company’s future performance might not be realistic.

Nonetheless, individuals often find themselves emotionally invested in their workplace.

It’s rare for someone to foresee a decline in their company’s prospects and continue working there.

More commonly, individuals with equity compensation appreciate their work environment, hold a positive view of their employer, and believe in the company’s potential growth.

Acknowledging and embracing these positive sentiments toward one’s company and its stock is reasonable.

Anyhow, it’s crucial to strike a balance between the desire to be part of the company’s growth and the reality that growth is not guaranteed, and investments come with uncertainties.

If you strongly believe in your company’s future but are contemplating whether to sell your stock, it’s a valid question that shouldn’t be dismissed.

Consider holding onto some shares while having a clear plan in place to manage and mitigate emotional influences.

For instance, a recommended approach is for clients to limit concentrated positions to no more than 10% of their liquid assets.

This applies to company stock as well.

This restriction helps prevent overexposure to risk and volatility.

Simultaneously, it contributes to a more balanced and well-managed investment portfolio.

Your Future With the Company

Looking ahead, it’s essential to contemplate the future trajectory of the company and how your role within it might evolve.

Your ongoing success and advancement within the organization can significantly influence both your compensation and the nature and quantity of equity you’re granted.

If you envision receiving more company stock in the future, it’s prudent to think about diversification as your equity holdings increase.

Establishing a systematic approach for managing company stock grants over time provides a framework for selling shares.

Especially, when it aligns with your circumstances, especially if you anticipate additional stock grants.

At the same time, if you perceive your current stock grant as a singular occurrence, holding onto a portion of those shares could be a sensible strategy.

This includes potentially more stock grants than you would if expecting additional grants.

This allows you to sustain your role as a shareholder and actively participate in the company’s growth.

Possible Gains and Losses

This question is perhaps the most crucial, and interestingly, it’s not specifically about your company or its stock.

It’s a broader inquiry that necessitates a degree of self-awareness and an understanding of your likely reactions in various scenarios.

It serves as the most accurate gauge of your genuine risk tolerance concerning the investments and assets you possess.

Consider this: What would be more disconcerting for you?

Selling a stock share for $50 today only to witness its value rise to $100 next year?

Or would it be more unsettling to hold a share valued at $50, driven by your belief in the company’s potential, only to see it diminish to $25 in a year, rendering your chance to sell at a higher price missed?

For many individuals, the prospect of a loss is more distressing.

The realization that a potential profit was within reach if only they had acted sooner is a significant source of investment regret.

Your feelings about this hypothetical situation can potentially indicate whether it is:

  • More prudent to sell your company stock now, securing the cash value.


  • if you are inclined to embrace the risk of potential value loss and retain shares to observe future developments.

Regularly Selling Company Stock

Another regular doubt that arises in the minds of several individuals is “When should I sell my company stock regularly?”

While owning a portion of the company you work for is gratifying, it’s advisable to regularly sell some of your company stock.

Here are the primary reasons why.


Since your career is likely your primary income source, having a significant portion of your net worth tied to your company introduces concentration risk.

By diversifying your exposure through selling some or all of your vested shares each year, you mitigate the impact of a potential decline in your company’s stock price.

This is especially true during downturns or bad management decisions.

Building Passive Investment Income:

Selling company stock allows you to generate passive income, especially if your company’s stock doesn’t pay dividends.

By reinvesting the proceeds into assets like dividend-paying stocks, REITs, bonds, or private real estate, you can create a diversified income stream.

This strategy helps to reduce reliance on unpredictable future cash flows and turns the gains from company stock into tangible assets.

Improving Quality of Life:

While investing for the future is essential, regularly selling company stock enables you to enjoy the benefits today.

Whether it’s funding vacations, buying a home, taking care of family, or covering education expenses, using the proceeds for immediate needs enhances your quality of life.

Paying for Taxes:

With Restricted Stock Units (RSUs), being taxed at vesting is common.

Selling some shares at vesting can help cover the resulting tax liability, which is based on the market value of the shares at vesting.

Holding shares for a year or longer after vesting may lead to long-term capital gains tax treatment, offering potential tax advantages.

Regularly evaluating your company stock holdings and considering these factors can help you make informed decisions that align with your financial goals and priorities.

Can I Sell My Company Shares to Anyone?

If you ever wondered “Can I sell my company shares to anyone” then, this section is particularly for you.

Whether you can sell your company stock to anyone depends on various factors, including the nature of your company’s stock and any legal or contractual restrictions in place.

Here are some considerations:

  • Publicly Traded Companies
  • Privately Held Companies
  • Legal and Regulatory Considerations
  • Shareholder Agreements and Restrictions
  • Lock-Up Periods
  • Company Policies

It’s crucial to thoroughly review all relevant documents, seek legal advice if needed, and understand the implications of selling your company stock.

Additionally, if you are part of a privately held company, coordinating with the company’s management and other shareholders is important to ensure a smooth process and compliance with any applicable restrictions or agreements.

Does Selling Stock Hurt a Company?

company stocks sales

Selling your company stock can have various implications, and the impact on your company and your ability to sell the stock to others depends on several factors:

  • Impact on the Company
  • Legal and Regulatory Considerations
  • Market Liquidity
  • Shareholder Agreements and Restrictions
  • Financial Planning

Before selling your company stock, it’s advisable to consult with financial advisors, legal counsel, or your company’s financial team to understand the potential implications, comply with regulations, and make informed decisions based on your circumstances.

How Much Should I Sell My Stock For?

Determining the appropriate selling price for your company stock involves a combination of factors, and the process can vary depending on whether your company is publicly traded or privately held. Here are some considerations for both scenarios:

Publicly Traded Companies:

  • Market Price
  • Current Valuation
  • Trading Trends

Privately Held Companies:

  • Valuation Methods
  • Independent Valuation
  • Negotiation
  • Rights of First Refusal
  • Future Potential
  • Legal and Financial Advice

Ultimately, the price at which you sell your company stock should reflect a fair and reasonable value based on the prevailing market conditions, the company’s financial performance, and any relevant contractual agreements.

Consulting with financial professionals and possibly engaging a valuation expert can provide valuable insights into determining an appropriate selling price.

Opt For the Right Decision

Deciding whether to sell or hold shares of company stock is a subjective choice that hinges on your individual goals, preferences, and overall financial plan.

There’s no definitive right or wrong answer.

The key is to avoid inaction or a lack of strategy when faced with the question of whether to sell or hold.

Taking some form of decisive action is essential. If you find yourself uncertain about the best course of action, consulting with a financial planner can provide valuable insights.

This will help you assess your options and arrive at an informed decision.

Bottom Line

Finally, employees should consider periodically selling a portion of their company’s stock.

This strategy allows for diversification, reducing concentration risk tied to the company’s performance.

Additionally, selling provides the opportunity to build passive investment income by reinvesting proceeds into diverse assets.

Enjoying the benefits today, such as improving the quality of life or covering immediate expenses, is equally important.

Moreover, selling can help manage tax implications, especially with instruments like Restricted Stock Units (RSUs).

Overall, a balanced approach to selling company stock aligns with financial goals and mitigates risks associated with concentrated positions.

That being said, I strongly hope that the information in this article helped you decide whether or not to sell company stock.

If you’re an expatriate or a high-net-worth individual in search of expert financial guidance or wealth management services, please don’t hesitate to reach out to me.

I’ve assisted numerous clients on their journey to financial independence, and you might be the next beneficiary of the personalized investment strategies I provide.

Pained by financial indecision? Want to invest with Adam?

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Adam is an internationally recognised author on financial matters, with over 760.2 million answer views on Quora.com, a widely sold book on Amazon, and a contributor on Forbes.



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