Lively HSA Investment Options Checklist (2026) | HSA Tracker

Confirm your Lively HSA account is fully set up and funded.

You cannot link an investment account or evaluate fee strategies without an active, funded HSA. This is the foundational step for all subsequent actions.

Decide if you will use the Schwab brokerage or the Devenir Guided Portfolio.

This choice dictates your fee structure, level of control, and investment approach. Schwab is for self-direction, Devenir for management at a 0.50% annual fee.

Choose your strategy for the $24 annual Schwab access fee.

You must decide to either pay the $24 fee for first-dollar investing or maintain a $3,000 minimum cash balance to avoid it. This impacts your upfront cash allocation.

Read the fee schedule for the Devenir Guided Portfolio.

The 0.50% annual management fee is deducted quarterly from your invested assets. Understand how this compares to other managed options, like Fidelity's 0.35% fee.

Check the current APY for the Lively cash account you are not using for the $3,000 minimum.

If you keep $3,000 in cash to avoid the $24 fee, that money earns minimal interest (as low as 0.02%). Weigh this opportunity cost against the fee.

Verify your HDHP eligibility for the current tax year.

You can only contribute to an HSA if enrolled in an HDHP meeting IRS requirements ($1,700 deductible self-only, $3,400 family for 2026). Investing does not change this rule.

Set a reminder to review investment fees annually.

Fee structures and interest rates can change. An annual review ensures your strategy remains cost-effective compared to other providers like Fidelity.

Determine your target HSA cash emergency fund balance.

This is the amount you keep in the Lively cash account for near-term medical expenses. It prevents you from having to sell investments during a market dip to pay a bill.

Calculate your annual HSA contribution limit for 2026.

Know your maximum allowed contribution ($4,400 self-only, $8,750 family, plus $1,000 catch-up if 55+). This defines how much new money you can invest each year.

Decide on an asset allocation for your invested HSA funds.

Your investment mix (stocks, bonds, ETFs) should match your time horizon and risk tolerance. Funds for expenses in 5 years should be more conservative than those for retirement in 30 years.

If using Schwab, select specific ETFs or mutual funds for your portfolio.

Schwab offers thousands of choices. Research low-cost, broad-market index funds to build a diversified core portfolio without high expense ratios.

Plan your rebalancing schedule for the investment portion.

Market movements can shift your asset allocation. Set a schedule (e.g., annually) to buy and sell assets to return to your target mix, maintaining your desired risk level.

Document your investment policy statement for the HSA.

A simple written plan outlines your goals, target allocation, and rules for contributions and withdrawals. It keeps you disciplined and provides guidance for a spouse or advisor.

Initiate the link between your Lively cash account and the Schwab brokerage.

This connection must be established before you can transfer funds to invest. Follow Lively's instructions within your online account dashboard to complete this setup.

Transfer funds from your Lively cash account to the Schwab investment account.

Money does not move automatically. You must manually initiate transfers to fund your brokerage account for investing, following the rules you set for your cash minimum.

Place your first trade or set up automatic investments in your chosen funds.

Uninvested cash in the brokerage account earns nothing. Execute your planned trades to put your money to work according to your asset allocation strategy.

Set up automatic monthly contributions from your paycheck or bank account.

Automation ensures consistent funding of your HSA, helping you hit your annual contribution limit and enabling dollar-cost averaging into your investments.

Configure automatic transfers from cash to investments once your emergency fund is full.

To maintain first-dollar investing or keep your cash at the target level, set a rule to sweep excess cash above your threshold into the investment account periodically.

Enable paperless statements and tax document delivery.

This ensures you receive your annual IRS Form 5498-SA and other tax documents promptly for accurate filing. It also reduces clutter and security risks from physical mail.

Download the Lively and Schwab mobile apps for on-the-go monitoring.

Mobile access lets you check balances, track investment performance, and even submit reimbursement requests quickly, keeping you engaged with your HSA strategy.

Consider paying current medical expenses out-of-pocket to preserve HSA funds.

If you can afford it, paying medical bills with after-tax money lets your HSA balance grow tax-free. You can reimburse yourself for those expenses years later, tax-free.

Organize a system for saving medical receipts for future reimbursement.

If you defer reimbursements, you need proof of qualified expenses. Use a digital folder or app to store receipts by date and amount. This is vital for IRS compliance.

Evaluate if a provider switch (e.g., to Fidelity) is warranted due to fees.

Periodically compare Lively's total costs (Schwab fee, Devenir 0.50%) against competitors. Fidelity has no investment fees and no minimums, which may save money for large balances.

Plan for Medicare enrollment and its impact on HSA contributions.

Once you enroll in Medicare Part A or B, you can no longer contribute to an HSA. Plan your final contributions in the year before you turn 65 to maximize the account.

Review the performance of the Devenir portfolio against a benchmark annually.

If using the managed portfolio, check if its net returns (after the 0.50% fee) are competitive with a simple low-cost index fund portfolio you could manage yourself.

Integrate your HSA asset allocation with your overall retirement portfolio.

View all your accounts (401k, IRA, HSA) as one portfolio. You might hold more bonds in your 401k and more growth-oriented assets in your HSA for better overall tax efficiency.