Side Hustle Success: 5 Financial Tips for Freelancers and Gig Economy Workers

Admin • August 25, 2023

The freelance and gig economy certainly has many attractive benefits. Many people want or need to supplement their primary income, others crave flexibility and variety, and some don’t want to be tied to a single physical location or the same schedule every day. Approximately 16% of the American workforce is comprised of gig workers with nearly half of gig workers also holding full-time jobs.

The high earning potential and ability to be your own boss lure many people into the freelance and gig economy world. But it’s important to remember and be prepared for the challenges that come with this type of work such as lack of insurance, differences in tax reporting, and irregular income. 

 

5 Financial Tips for Freelancers and Gig Economy Workers

With sufficient financial knowledge and self-discipline, you can be successful as a freelancer and accomplish your goals. Understanding these five concepts can help you start on the right foot. 

  1. You should diversify your income options. 
  2. You need to know your worth. 
  3. Become a master of your tax responsibilities. 
  4. Learn how to manage your fluctuating income. 
  5. Insure yourself today and invest in your future. 

These tips, along with regular and comprehensive financial planning will help you navigate the amazing world of side hustles, freelancing, and the gig economy. 

 

1. You should diversify your income options.

Finding success as a freelancer, especially when you freelance full-time, often takes a variety of skills. For example, if you work online as a virtual assistant, it’s best to be familiar with all the major bookkeeping software and customer relationship management (CRM) programs, as well as have strong communication and social media skills. Ensuring you’re the “complete package” will make you more marketable and valuable. 

It’s also important to diversify your skills and talents because freelance work can often be volatile. If your work is suddenly no longer needed with one client or platform, you’ll need to quickly pivot and find a new opportunity. Having a variety of skills under your belt will help decrease the amount of time you’re out of work. 

Take some time to research the services that are most in need and commit to learning them through online workshops, reading articles, or watching tutorials. As you continue working in the gig economy, never stop learning, increasing your skills, and adapting to the ever-changing landscape. 

 

2. You need to know your worth. 

Pricing yourself correctly as a freelancer is an extremely important part of being financially successful. Price yourself too high and you may find your inbox empty. Price yourself too low and you sell yourself short. There are many strategies you can use to discover your worth and price yourself: 

  • Discover what other freelancers are charging for similar services (remember, your specific experience and positive references will be a major factor in your worth and prices as a freelancer). 
  • Think about the expenses you will incur in your freelance work (including taxes!). 
  • Determine if you’ll charge an hourly rate or a project rate.
  • Think about the worth you are providing your clients. Oftentimes, your work is providing clients with intangible value and those benefits should not be overlooked. 
  • Pricing your goods and services is not a one-time task, you’ll want to continually evaluate your prices as your skills, experience, and expenses increase. 

 

3. Become a master of your tax responsibilities.

Freelancers and gig economy workers have to pay special attention to their taxes. Instead of the traditional W2 tax form, you will receive a 1099-NEC form from every client you worked for throughout the year. 

As a freelancer, you are responsible for paying self-employment tax (15.3%) as well as your standard income tax. Typically, your employer would pay for half of your Social Security and Medicare taxes, but as a freelance worker, you’re responsible for the entire portion. 

If you expect to owe more than $1,000 in taxes in any given year, you must pay part of your tax bill quarterly. You can use IRS Form 1040-ES to estimate how much you should pay for each quarterly tax payment. Some states also require freelancers to pay quarterly state income taxes. 

Because freelancers typically incur expenses that typical W2 employees don’t (for example, if a W2 employee needs a phone to perform their job duties, one is typically issued and paid for by the employer), they can claim tax deductions . 

Typical freelancer tax deductions include home office supplies, business-related meals and travel, required equipment, phone, and Internet services, certifications, and more. These deductions can drastically help reduce your tax liability, just ensure they are legitimate and properly documented. 

Because self-employed taxes can be so nuanced, it can be wise to hire a tax professional. They will be able to advise you on your quarterly tax payments, business structures, and tax deductions. 

 

4. Learn how to manage your fluctuating income. 

Irregular income can be challenging to budget, but it’s not impossible! Follow these guidelines to start your freelance budget today: 

  • Start by looking at your monthly expenses and determine what you need to earn every month to cover your essentials. 
  • If you don’t have one already, make a plan to build up an emergency fund to cover you for slower income seasons. 
  • Average your monthly income and create spending allowances for non-essential expenses. Allow yourself to spend money on fun items and experiences within reason. 
  • Use higher-earner months to fund your bigger goals. After knowing what you need to earn to cover your essentials and even a few non-essential expenses, you can save and invest any extra income for non-monthly expenses like a vacation or down payment on a home. 
  • Keep detailed records of your business expenses—this will save you money and time during tax season.
  • Always overestimate your expenses and underestimate your income. 

And while we’re on the topic of getting income, invoice management is a skill you will want to master, regardless of the field you’re in. Here are some tips to get you started: 

  • Request a deposit before starting work on a project. 
  • Automate your invoicing and ask consistent clients to sign-up for automatic payments. 
  • Be clear about your payment terms and don’t be afraid to tack on late-payment fees. 
  • Keep records of all invoices. 

It’s solely your responsibility to make sure you get paid. By having automatic, professional systems in place, this process can become streamlined and easy to manage. 

 

5. Insure yourself today and invest in your future. 

Health insurance is often offered at a free or reduced rate from W2 employers, but as a freelancer, it’s up to you to secure your own health insurance plan. You can apply for coverage through Health Insurance Marketplace and thankfully, your premiums are tax-deductible ! You don’t want an unexpected medical expense to derail your financial freelancing progress. 

Retirement contributions through paycheck deductions are common with W2 contracts as well. As a freelancer, you’ll want to ensure you’re not putting off your retirement contributions. You can contribute to a: 

Before committing to a certain retirement plan, take time to understand the contribution limits, withdrawal rules, and tax implications so you can choose the best option for your financial situation. 

Navigate the Gig Economy with Five Pine Wealth Management

At Five Pine Wealth Management , we can help you navigate your various income sources while providing you with comprehensive retirement, investment, tax, and goal-planning advice. Whether you are a full-time freelancer or supplementing your primary income, you want to ensure you’re using your money in the most strategic way possible. 

To see how we can help you today, email us at info@fivepinewealth.com or give us a call at 877.333.1015. We can’t wait to hear from you! 

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401(k) Millionaire: Proven Strategies to Reach 7 Figures in Your Retirement Account

October 17, 2025
Key Takeaways Maxing out your employer match provides an immediate 50-100% return and is the easiest way to accelerate your 401(k) growth. Reaching $1 million in your 401(k) depends more on consistent contributions over time than on being the highest earner or picking winning investments. High earners can potentially contribute up to $70,000 annually through a mega backdoor Roth conversion if their employer plan allows after-tax contributions. Hitting seven figures in your 401(k) might sound like a pipe dream, but it's more achievable than you think. With the right 401(k) investment strategies and a disciplined approach, becoming a 401(k) millionaire is within reach for many mid-career professionals. Let's walk through exactly how you can get there. The Math Behind Becoming a 401(k) Millionaire Before we discuss strategies, let's look at the numbers. Understanding the math helps you see that reaching $1 million isn't about getting lucky — it's about time, consistency, and thoughtful planning. Starting Age Annual Contribution Balance at 65* 30 $15,000 $1.5 million 30 $20,000 $2 million 40 $25,000 $1.3 million *Assumes 7% average annual return Time matters, but it's never too late to build substantial wealth if you're willing to prioritize your retirement savings. 7 Steps to Build Your 401(k) to Seven Figures Now that you understand the math, let's break down the specific strategies that will get you there. Step 1: Max Out Your Employer Match (The Easiest Money You'll Ever Make) If your employer offers a 401(k) match, contributing enough to capture it fully is the absolute first step: it’s free money that provides an immediate 50-100% return on your investment. Let's say your employer matches 50% of your contributions up to 6% of your salary. If you earn $150,000 and contribute $9,000 (6% of your salary), your employer adds $4,500. That's a guaranteed 50% return before your money even hits the market. Not taking full advantage of an employer match is like turning down a raise. Make sure you're contributing at least enough to capture every dollar your employer offers. Step 2: Gradually Increase Your Contribution Rate Once you've secured your employer match, the next step is increasing your personal contribution rate over time. For 2025, the 401(k) contribution limit is $23,500 (or $31,000 if you're 50 or older with catch-up contributions). Here's a practical approach: Every time you get a raise or bonus, direct at least half toward your 401(k). If you get a 4% raise, bump your contribution by 2%. Many plans now offer automatic annual increases. If yours does, set it to increase your contribution by 1-2% annually until you hit the maximum. You'll barely notice the change, but your future self will thank you. Step 3: Master Tax-Advantaged Retirement Accounts Through Strategic Contributions Traditional 401(k) contributions reduce your taxable income now, which is ideal if you're in a high tax bracket today. Roth 401(k) contributions don't reduce current taxes, but withdrawals in retirement are tax-free — valuable if you're earlier in your career or expect a higher income later. A hybrid approach works for many of our clients. Step 4: Optimize Your 401(k) Investment Strategies Your contribution rate matters, but so does what you're investing in. We regularly see clients who contribute aggressively but choose overly conservative investments that don't provide enough growth. Keep costs low . Target-date funds and index funds typically offer the lowest expense ratios. Every 0.5% in fees you avoid can add tens of thousands to your retirement balance over 30 years. Rebalance annually . Market movements throw your allocation off balance. Set a reminder once a year to review and rebalance your portfolio back to your target allocation. Avoid the temptation to chase performance . Last year's top-performing fund is rarely this year's winner. Stick with broadly diversified, low-cost options. Step 5: Consider a Mega Backdoor Roth Conversion If you're a high earner who's already maxing out regular 401(k) contributions, a mega backdoor Roth conversion can accelerate your retirement savings. Here's how it works: Some employer plans allow after-tax contributions beyond the standard $23,500 limit. The total contribution limit for 2025 (including employer contributions and after-tax contributions) is $70,000 ($77,500 if you're 50+). If your plan permits, you can make after-tax contributions up to that limit, then immediately convert those contributions to a Roth 401(k) or roll them into a Roth IRA. This gives you tax-free growth on substantially more money than the regular contribution limits allow. Not all plans offer this option, and the rules can be complex. Check with your HR department to see if your plan allows after-tax contributions and in-plan Roth conversions or rollovers. Step 6: Avoid These Common 401(k) Mistakes Even with great 401(k) investment strategies, mistakes can derail your progress toward seven figures. Avoid: Taking loans from your 401(k) . While it might seem convenient, you're robbing yourself of compound growth. The money you borrow stops working for you, and you're paying yourself back with after-tax dollars. Cashing out when changing jobs . Rolling over your 401(k) to your new employer's plan or an IRA allows your money to continue growing tax-deferred. Cashing out triggers taxes and penalties that can set you back years. Panic selling during market downturns . Market volatility is normal. The clients who reach $1 million are those who stay invested through ups and downs, not those who try to time the market. Step 7: Stay Consistent (Even When It's Boring) The path to becoming a 401(k) millionaire isn't exciting (and that’s a good thing!). The most successful savers aren't those who constantly tweak their strategy or chase the latest investment trend. They're the ones who set up automatic contributions, review their allocation once a year, and otherwise leave their 401(k) alone. Let Five Pine Help You Build Your Million-Dollar Plan Reaching $1 million in your 401(k) is absolutely achievable with the right strategy and discipline. Whether you're just starting your career or playing catch-up in your 40s and 50s, the steps remain the same: maximize contributions, optimize your investments, take advantage of tax-advantaged retirement accounts, and stay consistent. At Five Pine Wealth Management , we help clients build comprehensive retirement strategies that go beyond just their 401(k). We can analyze your current contributions, recommend optimal allocation strategies, and help you coordinate your employer plan with other retirement accounts. Want to see what your path to seven figures looks like? We help clients build these roadmaps every day. Email us at info@fivepinewealth.com or give us a call at 877.333.1015. Let's talk about your specific situation. Frequently Asked Questions (FAQs) Q: Should I prioritize maxing out my 401(k) or paying off debt first? A: Start by contributing enough to capture your full employer match — that's an immediate 50-100% return you can't get anywhere else. Beyond that, prioritize high-interest debt (credit cards, personal loans) since those interest rates typically exceed investment returns. Q: Should I stop contributing during market downturns to avoid losses? A: No — continuing to contribute during downturns is actually one of the best strategies for building wealth. When prices are lower, your contributions buy more shares, setting you up for greater gains when the market recovers. Q: I'm 55 with only $300K saved. Is it too late to reach $1 million?  A : While reaching exactly $1 million by 65 might be challenging, you can still build substantial wealth. Maxing out contributions, including catch-up ($31,000/year), could get you to $750K-$850K depending on returns. Disclaimer: This is not tax or investment advice. Individuals should consult with a qualified professional for recommendations appropriate to their specific situation.

Couples Money Management: Why Both Spouses Need to Know Where the Money Is

October 17, 2025
Key Takeaways Both spouses should understand the family’s finances, even if only one manages them, to prevent confusion or stress during life’s unexpected events. Regular money check-ins, shared account access, and attending financial planning meetings together help couples build confidence and clarity. Partnering with a fiduciary advisor ensures both spouses have support, education, and guidance for comprehensive wealth management and long-term peace of mind. Money is one of the most common sources of stress in relationships. Some couples argue about spending habits, while others quietly hand off all financial responsibilities to one spouse and never revisit the arrangement. At first glance, this setup can feel efficient: one partner pays the bills, manages investments, and handles taxes while the other takes care of different responsibilities. However, there is a risk to this method. If something unexpected happens, the spouse who hasn’t been involved in financial decisions can feel completely lost. Even highly capable, intelligent people often tell us they don’t know where accounts are located, how much income is coming in, or what investments they own. When life throws a curveball, like illness, death, or divorce, that lack of knowledge creates unnecessary anxiety during an already difficult time. The solution is not to necessarily make both partners money managers, but to ensure both understand the big picture. Let’s walk through why this matters, what it looks like in practice, and how you can start today. Financial Planning for Couples Effective financial planning for couples goes beyond having the right investment mix or adequate insurance coverage. It requires both spouses to understand the big picture of their financial life, even if only one manages the day-to-day details. This doesn't mean both partners need to become financial experts. Instead, it means creating transparency and basic literacy that protects your family's financial security regardless of what life throws at you. Here are a few essentials: Regular check-ins : Schedule monthly or quarterly “money talks” where you review accounts, upcoming expenses, and investment performance. This keeps both partners informed. Shared access : Make sure both spouses have login information for bank, investment, and retirement accounts. A secure password manager can help keep things organized. Big-picture clarity : Even if one spouse handles the details, both should know where you stand with assets, liabilities, income, and goals. Think of it as insurance against uncertainty. If one spouse suddenly has to take the reins, they aren’t starting from zero. Couples Money Management Couples' money management doesn’t have to mean “50/50 responsibility for every financial task.” Instead, think about it as defining roles while keeping communication open. Many households operate on a “primary manager” system. One person writes the checks, monitors the accounts, and interacts with financial advisors. That’s perfectly fine, as long as the other spouse has visibility. Problems arise when the "non-manager" is completely shut out. Some practical ways to stay connected: Attend meetings together : Whether it’s with your accountant, attorney, or financial planner, both spouses should be present. Hearing the same information firsthand helps prevent misunderstandings. Document everything : Create a simple household financial binder (digital or physical) that includes account numbers, insurance policies, estate documents, and contact info for professionals you work with. Ask questions : No question is too small. If you don’t understand how an investment works or why you own it, speak up. Practice decision-making together: Involve both partners in financial decisions, even small ones. This builds confidence and familiarity with your financial priorities and decision-making process. Fiduciary Financial Planning: The Professional Partnership Advantage Working with a fiduciary financial advisor creates an additional layer of protection for couples navigating financial planning together. Fiduciary advisors are legally required to act in your best interest, providing objective guidance that supports both partners' financial security. A good fiduciary advisor will insist on meeting with both spouses regularly, ensuring that financial strategies are understood and agreed upon by both partners. They can also provide education and support to help less financially-inclined spouses build confidence and understanding over time. This professional relationship becomes especially valuable during transitions. When one spouse dies or becomes incapacitated, having an advisor who knows both partners and understands the family's complete financial picture provides stability during chaos. Comprehensive Wealth Management Comprehensive wealth management goes beyond investments. It covers cash flow, taxes, estate planning, insurance, and long-term care strategies. For couples, it also means creating contingency plans. What happens if one spouse passes away? Will the survivor know how to access accounts? What if the “financial spouse” faces cognitive decline later in life? Will the other partner have the confidence to step in? These are not fun scenarios to imagine, but planning for them is an act of love. Comprehensive wealth management ensures: Estate documents are in place and up to date (wills, powers of attorney, trusts). Beneficiaries are correct on retirement accounts, insurance, and other assets. Tax planning strategies are understood by both spouses, so surprises don’t derail long-term goals. Cash flow is sustainable even if income sources shift (such as after retirement or the loss of a business owner’s salary). When couples approach wealth management together, they reduce the risk of financial upheaval during life’s transitions. When Life Changes Everything: Rebuilding Financial Confidence After Loss Despite the best preparation, losing a spouse creates emotional and financial challenges that feel overwhelming. If you find yourself suddenly managing finances alone, remember that feeling lost is normal and temporary. Start by taking inventory of your immediate needs. Focus on essential expenses and cash flow first. Most other financial decisions can wait while you process your grief and adjust to your new reality. Don't make significant financial changes immediately. Grief affects judgment, and rushed decisions often create problems later. Give yourself time to understand your new situation before making significant moves. Lean on your professional team. This is exactly when having existing relationships with financial advisors, attorneys, and accountants becomes invaluable. They can provide stability and guidance during an unstable time. Consider working with a counselor who specializes in financial therapy or grief counseling. Processing the emotional aspects of sudden financial responsibility is just as important as understanding the technical details. Taking the Next Step Together If you and your spouse have fallen into the habit of letting one person manage all the finances, it’s not too late to shift. Schedule a money talk this week. Write down your accounts. Ask questions. Set a reminder to attend your next financial planning meeting together. At Five Pine Wealth Management , we can guide couples through these conversations. Whether you’re in the wealth accumulation phase, approaching retirement, or already enjoying it, we help both partners feel equally confident in their financial picture. Don't wait until a crisis forces financial literacy upon you. Call (877.333.1015) or send us an email today at info@fivepinewealth.com to schedule a consultation and start building the financial transparency and security your family deserves. Frequently Asked Questions (FAQs) Q: What if one spouse has no interest in learning about finances? A: Start small and focus on the essentials. Your spouse doesn't need to become a financial expert, but they should know where important documents are located, understand your basic monthly expenses, and know how to contact your financial advisor. Q: How often should we review our finances together if only one person manages them day-to-day? A: Quarterly check-ins work well for most couples. Schedule a regular 30-minute conversation to review your progress toward goals, discuss any major upcoming expenses, and ensure both partners stay informed about your overall financial picture. Q: What's the most important thing for the non-financial spouse to understand first?  A: Cash flow and immediate needs. Know where your checking accounts are, how much you typically spend each month, what bills are on autopay, and how to access emergency funds. This knowledge provides immediate stability if they suddenly need to take over financial management.