Have Shares Already? Here’s How to Decide if You Should Start Again


Disclosure: This article is not intended to be financial advice and information should be taken as educational only. Read the disclaimer.

Ever feel like your stock portfolio is that old friend you hang out with but don't really connect with anymore?

You know, comfortable but kind of uninspiring?

It could be that are in the investment ‘friend zone'.

And let's face it, your money deserves passion, not just a ‘meh' kind of relationship.

So it might be time to go from ‘just friends' with your portfolio to ‘soulmates'?

Today I want to dive into why you might be second-guessing your portfolio, and what options you have to either spice things up or make a clean break.

If you're thinking to yourself “Is it time to just start all over?” then you're not alone and I'm going to break down the considerations you need to make before taking that leap.

Why You Might Be Second-Guessing Your Portfolio

If you're considering a reset, it's crucial to first understand the reasons that have led you to this crossroad.

Let's try and understand why you're in this place.

Is it lack confidence, emotional attachments, or perhaps the allure of greener pastures?

Firstly, don't sweat it—you're not alone.

The doubts you're experiencing are completely normal.

I personally know of many times I've felt like this I just want to throw everything I've built out the window.

Here's some of the common reasons I've felt like giving up and maybe wanted to start all over again.

Lack of Confidence

So, you've got this assortment of shares, and you can't help but feel like you're cobbling together a financial plan on the fly.

You're asking yourself, “Do I even know what I'm doing?”

I've felt that way myself.

My early investment journey can probably be described as experimental in hindsight.

I picked random stocks, stockpiled ETFs and had a go at crypto.

I realized over time that a portfolio that feels like a patchwork quilt isn't great for your confidence.

Yes, investing can become messy and that's not a bad thing some simplification and clarity can improve that confidence (more on that later).

What's important is that you don't blame where you're at on the craft of investing, but treat it as a learning experience.

Investing is proven to be a long-term wealth building system.

Too sentimental

Maybe you've got shares in a company you've worked for, a gift from family or the very first recommendation you received.

And you're struggling to move on from something that has sentimental value.

These emotional ties are natural but can cloud your judgment.

The important thing is to recognize these feelings for what they are—emotional triggers that may not align with your financial goals.

Sometimes an investment is just a part of your journey for a limited time.

There to do a certain job.

I used to work for both Telstra and Wesfarmers and got access to shares as part of the employee share plan.

On paper, these were great companies.

But when I stepped back and looked at my entire investment strategy, I realized these shares were more about my past than my future.

I was holding onto them partly because they were remnants of my career journey.

Ultimately, I decided to sell them off and invest in ETFs, which better aligned with my broader financial objectives.

Fear of Missing Out (FOMO)

Who hasn't felt the pang of regret at a missed opportunity?

Perhaps you're watching certain stocks soar while yours are just sort of… meh.

Or maybe your mate Steve can't stop talking about how he invested in a trending tech startup and doubled his money in just six months.

FOMO is a classic emotion many investors face; it's part of the learning curve.

Don't think of investing as a competition.

Steve's risk tolerance and financial goals are likely different from yours.

Stick to your game plan or adjust it thoughtfully—not impulsively.

If you do need help setting one up, then maybe I can help put one together with you?

Just remember that the investment landscape is always moving.

Hot trends and stocks come and go.

There will always be other opportunities.

And you don't need to be involved in everything.

The Decision-Making Process

So, you might've figured out why you're doubting your portfolio.

But before you go all Marie Kondo on your shares, let's talk about the nitty-gritty of how to decide what stays and what goes.

Audit Your Current Portfolio

First things first—take a hard look at what you’ve got.

Are your investments diverse, or are you putting all your eggs in one basket?

Also, how are they performing against your financial goals?

I used to hang onto underperforming shares longer than I should've, thinking they'd eventually bounce back.

It wasn't until I put everything under the microscope that I made some strategic moves.

Understanding Risk Tolerance

What keeps you up at night?

If it's worrying about your investments, you need to reevaluate your risk tolerance.

This doesn't mean turning into a day-trader or going ultra-conservative, but finding that sweet spot where you're comfortable with the level of risk you're taking on.

In financial media, the topic of risk often gets glossed over—maybe because it's hard to explain.

But for me, it's simple: Can I invest in something and still sleep comfortably at night, regardless of how it performs?

Identifying Better Opportunities

If you find that some of your current shares are just collecting virtual dust, maybe you're contemplating whether to stick it out or head for the exit.

You're not alone, and it's completely normal to second-guess your investment decisions.

In fact, it's a sign that you're becoming more mindful of where your money is going.

But before you make any drastic moves like selling off everything, it's crucial to weigh your options carefully.

Is a fresh start the only path, or are there other avenues worth exploring?

The Options You Have

After some serious introspection and a detailed review of your portfolio, you're probably itching to take some kind of action.

But here's where you might hit the brakes—because ripping it all apart and starting from scratch might not be your only, or even your best, move.

You've got choices, and making an informed decision can spell the difference between investment regret and financial serenity.

Sell Everything and Start Again

If you're considering this route, know that selling your entire portfolio is a significant decision.

There are costs involved, like transaction fees and potential taxes.

It's also crucial to consider why you want to start over and what your new investment goals will be.

It’s a big move, but if it aligns with your long-term plans, it might be the right one.

Pivot to Other Investments

Don’t feel like you need to sell everything to make a positive change.

You can keep some of your stocks and diversify by adding other assets (like ETFs).

This approach allows you to mitigate risk without losing any ground.

It's like adding another tool to your toolkit without getting rid of your old favorites.

This is a strategy I've used before.

I leave what I have sitting there and go into something that I feel much more confident in.

That way there are no implications of selling and just balance out the investments I'm not confident in with ones I am.

Do Nothing and Stay the Course

Sometimes the best decision is not to make any changes.

Markets have ups and downs.

Emotional decisions often lead to mistakes.

If you feel that your portfolio is fundamentally sound but are only questioning it due to recent bad news or poor performance, maybe the best move is to do nothing for now.

Take a break, focus on other things, and come back to assess the situation later.

Your Portfolio, Your Choice

So there you have it—the why, the how, and the what now.

At the end of the day, the decision to start over or stay the course with your existing portfolio is deeply personal.

The key takeaway is to make that decision consciously, armed with all the facts and a clear understanding of your own financial goals and risk tolerance.

Whether you decide to overhaul your portfolio, make some tweaks, diversify a bit, or even sit tight and do nothing, each option has its own merits and drawbacks.

What's most important is that you're actively engaging with your investments, not just letting them drift aimlessly.

If you've been down this road before, you'll know that the investing world is far from static.

Circumstances change, and it's okay for your strategy to evolve too.

So take a breath, give it some thought, and make the choice that feels right for you.

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Tim Ellis, creator of DadInvestor.com.au, helps people confidently invest and manage their money. Inspired by his own experiences, Tim is passionate about creating a financially secure future for his family and sharing his personal finance knowledge with others.

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