Portfolios rarely stay simple forever. As wealth grows, complexity increases. It means added layers of rules and tax considerations, as well as a larger range of investment and structural options to consider. At some point complexity reaches a threshold which warrants professional help.

Earlier this year I spoke with my colleague Simonelle Mody about my new year’s resolution for 2026.

My situation is no longer straightforward. I have an Employee Share Plan which makes up part of my compensation, I am married and have opportunities to consider tax and investing strategies that may be more efficient, I have assets that I didn’t have before that justify a professional will instead of a simple will from an online provider. The list goes on.

I have reached a point where an opinion from an experienced professional about my strategy will either open new opportunities for me or grant me peace of mind that I am on the right track.

Below, I run through some clear signs that you may need professional financial or tax advice.

When tax strategy becomes more influential to investing outcomes

One of the clearest signals that an accountant may be valuable is when tax considerations begin to meaningfully influence investment decisions.

When you have a small investment portfolio, taxes are usually straightforward. As your portfolio grows, the tax landscape becomes more complicated. You may hold multiple asset classes across difference structures – superannuation, outside of super, family trusts, companies. Each structure has different tax treatments for income, capital gains and distributions.

Decisions become less clear cut about where to hold assets and your choices can have significant tax consequences. High income assets may be better places in tax-advantaged environments, while growth assets may be held in structures where capital gains discounts apply.

As investors, it is our job to be informed about our holdings and understand how they connect to our financial goals. Many of us are not full-time investors. It is difficult to stay on top of constantly changing tax and investment regulation, investment product rules and mandates, and all our reporting.

Strategies like tax-loss harvesting and timing of capital gains realisations can be meaningful contributors to overall returns. These strategies require careful record-keeping and detailed understanding of tax rules. Accountants become less of a compliance necessity and more of a strategic partner.

Multiple income streams

Another trigger for professional help is having multiple income streams.

You may earn your income from a mix of sources – your salary, bonuses, equity compensation, investment income or business income. Each source may have different tax implications and reporting requirements.

For example – if you’re invested in an Exchange Traded Fund (ETF) you may deal with distributions and capital gains. If you’re invested in a rental property, you may deal with depreciation schedules, deductible expenses and capital gains. An employee share plan will involve navigating vesting periods, cashflow management and sometimes currency record keeping.

Forecasting tax obligations become more complex. Planning ahead, rather than reacting, can significantly improve outcomes and manage cashflow with tax debts. Accountants can be valuable here.

Structural decisions

There are several vehicles you can invest through, and each carries their own tax benefits. Assets can be held personally, within superannuation, through a company or through a trust. Investment debt can be structured in different ways, including with debt recycling. Assets can be divided between partners which can minimise tax payable.

These are decisions that require careful analysis and purposeful decision making as they are difficult to reverse once implemented, given they often carry long-term tax implications. Holding assets in the wrong structure can be a mistake that compounds over decades.

This is where financial advisers may become useful. They can integrate investment strategy with broader financial planning decisions such as retirement, cash flow and estate planning. They can look at your situation on a holistic basis and offer advice around the most beneficial decision for the long-term.

Behavioural coaches

I have written a piece about the areas where advisers can add up to 3% to your return. One of the reasons is that they can help you maintain discipline during periods of market stress. If you are an investor that is prone to making poor decisions during market volatility, a professional can safeguard your assets and investments and offer a layer of removal from your investment accounts.

They can help you to remain focused on strategy, rather than short-term market movements.

We can’t forget about cost

Although ongoing financial advice fees are usually percentage based, many initial upfront costs are flat fee based. Accountants are almost always flat-fee or hourly charge based. The decision to engage professionals should ultimately come down to value. Professional services are a cost to your portfolio and must be weighed against the benefits provided.

Value emerges through improved tax efficiency, better structural decisions and reduced behavioural mistakes. One major tax error or poorly structured investment can often offset years of professional fees. However, if your portfolio is still simple and straightforward, the flat-fee cost may unnecessarily eat into your total return.

It is also important to recognise that professional help does not mean relinquishing control. It is our job to be invested in our outcomes and informed of the decisions that are made with our portfolio. It is a partnership where you are seeking advice, instead of outsourcing your decisions entirely.

Think you need a financial adviser or accountant? Here are some tips to find a good one.

Subscribe to get Morningstar insights in your inbox