6 Financial Truths About Self Employment

You may believe it’s easy to become self-employed or to start your own business. Yet, there are several financial realities that should make you stop and think. However, if you are really eager to become self-employed, you shouldn’t let these concerns stop you from reaching your goals. If you have a good financial plan in place, you may be able to avoid pitfalls.


1. Startup Expenses Can be a Barrier

If you were previously a salaried employee, you’ve perhaps not counted the minimal perks you get from the job. Everything you need to do the work is provided for you. You work in a space that someone else pays for. You enjoy the occasional office birthday party with free cake. When you are self-employed, you’ll have to procure the assets you need to do the job yourself. You will have to maintain upkeep on those assets as well as on the space where you do the work. Startup costs can pile up quickly. The costs may include things like commercial banking services and insurance.


2. Health Benefits

As with now having to provide your own tools of the trade, you’re also going to have to make up for other benefits you held previously. You will have to provide your own health insurance. If you have a family, the costs will be significant.


Under the Affordable Care Act, you may have qualified for health insurance premium subsidies in your state. The subsidy will lower the costs of the plan. Still, the plans available to you in the marketplace may be expensive.


The Small Business Jobs Act brings some health insurance cost mitigation to you at tax time. The law authorizes you to deduct an employer-equivalent portion of your health insurance costs from your taxes.


3. Your Tax Situation May Become Complicated

Tax time may present a completely new set of financial issues for you when you become self-employed. For consultant or freelancers who don’t itemize, there won’t be a significant change. You’ll be responsible now for paying the FICA tax, which is included in the self-employment tax rate. It will be in addition to the income tax you owe. You can chose to pay your taxes quarterly or wait until April and pay them all at once.


Conversely, self-employment will allow for new deductions. For example, if you have a home office, you may be able to deduct a portion of that. You can deduct business-related travel expenses. You may also be able to deduct the cost of paying a financial advisor to help you figure it all out.


4. Budgeting Will be a Challenge

Especially when you first start out as a self-employed, you may miss the predictable, regular income stream you had through your old job. Setting a budget is much easier when you know how much will be in your account each month. For some self-employment jobs, like seasonal work, your highs and lows may be predictable. For other jobs, like consulting, it may be hard to gauge how to handle things. The safe bet may be to save during the feast so that you can eat during the famine.


5. Saving for Your Retirement Will be Different

When you’re an employee, the employer looks out for your future by contributing to your retirement plan. Once you’re self-employed, you have to save for your own retirement. On one hand, some self-employment jobs may allow you to work beyond expected retirement years. However, you should ask yourself if you want to continue working at 70.


6. Preparing for the Worst

Somewhat related to issues like the difficulty in budgeting and saving for a rainy day is the possibility your business endeavor may not meet your goals. If you start a food service business, you may be in the position that many people who open restaurants are in; they must close up shop. You will need a plan to prepare for this possibility. Before jumping into the world of the self-employed, talk to one of our Lead Advisors to see how to best proceed.


This content is developed from sources believed to be providing accurate information. It may not be used for the purpose of avoiding any federal tax penalties. Please consult legal or tax professionals for specific information regarding your individual situation. The opinions expressed and material provided are for general information, and should not be considered a solicitation for the purchase or sale of any security.


Recent Buttonwood Articles


Investmen
By Dale Raimann January 7, 2026
As we closed out 2025, our Investment Policy Committee (IPC) continued its work to refine strategies that balance risk, liquidity, and long-term growth. In our previous update , we shared how the inflation shock of 2022 reshaped our approach to fixed income and led to a more nimble, systematic positioning of bond assets. That proactive discipline remains a cornerstone of our investment process. As we wrapped up 2025, our Investment Policy Committee (IPC) continues efforts to refine strategies that balance risk, liquidity, and long-term growth. With the Fed reducing overnight lending rates for the third time, recent IPC discussions have turned to another critical focus area: cash management. Why Cash Strategy Matters Now With interest rates still elevated and market uncertainty persisting, many investors hold larger-than-usual cash positions. While cash provides stability, it also introduces opportunity cost if left idle. One of our IPC objectives is to ensure that excess cash works harder for you, without compromising liquidity for emergencies or near-term cash needs. Refining Our Cash Allocation Policy For our clients with larger cash needs (generally more than 5% or $50k of liquid assets in cash or money market funds), we are shifting to a proactive T-Bill management strategy, or other suitable investments based on goals and circumstances. For our clients holding less than $50k in cash or money market, we have retained money market for liquidity, but we have made a switch to the default money market fund we are using. Risk and Tax Aware Money Market Selection While yields are similar across money markets today, the underlying investments in each money market fund vary quite a bit. For example, Schwab Prime Money Market (ticker SWVXX) offers a slightly higher yield but invests in asset-backed commercial paper (ABCP), introducing a modest credit risk. In contrast, Schwab Government Money Market (ticker SNVXX), invests primarily in U.S. Treasuries and government-backed securities, making it virtually risk-free and often state income tax-advantaged. With lower risk and only about 10/100’s of 1% yield difference, our IPC has proactively transitioned clients from SWVXX to SNVXX, to prioritize safety and tax efficiency over a marginal yield difference. Connecting Back to Our Broader Strategy These cash management refinements build on the fixed income strategy we recently outlined. By reducing exposure to inflation-sensitive bonds and implementing a more systematic approach, we are positioning portfolios to be more resilient across potentially weaker or higher-rate environments. Optimizing cash allocations and minimizing credit risk within money markets reinforces the same core principle—protecting downside risk while prudently capturing incremental return opportunities. Looking Ahead As we enter 2026, our investment approach remains focused and disciplined. We continue to prioritize liquidity for cash needs, thoughtful risk management, and systematic investment strategies designed to adapt to evolving market and economic conditions. This proactive framework supports long-term portfolio resilience while remaining aligned with your financial objectives. If you have questions about how these updates may impact your investments, cash management, or overall financial plan, we encourage you to connect with your financial advisor at Buttonwood. Our team is committed to delivering personalized wealth management and asset allocation strategies—regardless of market or economic uncertainty. Thank you for your continued trust and for allowing us to coordinate your asset management as part of our Family CFO services.
How to Talk About Money with Family Over the Holidays
December 23, 2025
How to Talk About Money with Family Over the Holidays. Whether your family is just beginning to plan or has been navigating financial decisions across generations
December 12, 2025
As year-end approaches, many clients focus on charitable giving—supporting causes they care about while optimizing their tax strategy. This year carries added urgency: the One Big Beautiful Bill Act (OBBBA) will significantly change charitable giving rules in 2026.
Buttonwood Investment Policy Committee Update
By Jon McGraw November 24, 2025
Maintain diversification as one of our risk management tools, focusing on our high-conviction ideas that tie with where we feel we are in the economic cycle.
Buttonwood Investment Policy Committee Update
By Kyle Hogan September 26, 2025
Our Investment Policy Committee (IPC) remains focused on balancing opportunity with discipline as markets continue to react to shifting economic and geopolitical dynamics. Following a volatile start to the year, recent developments have created a more constructive environment for risk assets, though caution remains war
Inside the Capitol Building, where the
By Jon McGraw July 21, 2025
On July 4, 2025, President Trump signed the One Big Beautiful Bill Act into law. Learn what that means for business owners.

Are you ready to explore the benefits of your very own Family CFO?

LET'S TALK

Buttonwood Services


About Buttonwood Financial Group