Written by Brittney Burgett, marketing consultant at Burgett Works and Waldman Accounting client
When I was laid off from my full-time job with just two weeks of severance, I suddenly had to figure out what came next. I’d always been a W-2 employee — taxes withheld automatically, benefits chosen from a list — and I had no idea what it meant to be “self-employed.”
Thankfully, I was connected with Ian Waldman, Owner & Founder of Waldman Accounting, through a previous employer. I reached out for guidance, and Ian encouraged me to explore becoming an independent contractor. He explained that setting up everything — financially and from a tax perspective — wasn’t as scary as it seemed.
Waldman Accounting’s guidance turned what could have been a stressful, confusing transition into one of the most rewarding experiences of my career. Here’s what I learned about starting out on my own and getting my financial life organized.
1. Don’t be afraid to bet on yourself and go out on your own
Losing a job is scary, but it can also be the push you need to build something better. Becoming an independent contractor or consultant gives you flexibility and control — over your time, your clients, and your income.
I’ve learned that multiple income streams bring me far more peace of mind than relying on a single employer to maintain my quality of life.
The part that feels overwhelming at first is usually the administrative side: taxes, invoicing, insurance, retirement planning, setting up your business entity. But once I had professional guidance, I realized how manageable it all is. With the right structure and systems, you can build stability and peace of mind even without an employer’s safety net — and in my opinion, it feels even more stable.
2. Get expert advice when setting up your business
My first call after the layoff was to Waldman Accounting. Ian walked me through setting up my LLC and naming my business, explaining why that structure made sense for liability protection and long-term tax flexibility — and how the LLC was the first step toward becoming an S-Corp. (Fun fact: Ian even came up with the name of my marketing business, Burgett Works.)
Once the business was established, Ian helped me elect S-Corporation status, which allowed me to pay myself a reasonable salary and take additional profits as distributions — reducing my self-employment tax burden.
I opted to pay Waldman Accounting’s very reasonable hourly rate to handle the forms and walk me through where to send everything. It was economical and saved me the time and stress of trying to DIY the setup process.
If you’re considering going out on your own, I recommend setting up your business now so you’re ready with your admin buttoned up from day one. We had a little cleanup work to do transitioning all my income to the LLC, but thanks to Waldman Accounting’s help, it was all completely approachable.
3. Tax-smart insurance shopping
With the high cost of healthcare in the U.S., one of the biggest worries people have about self-employment is health insurance. When I tell people I went out on my own, the first question is always, “What did you do about insurance?”
I didn’t realize how much health insurance decisions affect your taxes. When I needed guidance, Waldman Accounting connected me with a licensed insurance advisor who helped me find a Marketplace health insurance plan that balanced cost, coverage, and tax impact. Waldman Accounting has since expanded to offer insurance services in-house, helping clients compare plans and understand the tax implications of each choice.
I ended up with a plan that fit my needs and budget — just $275 a month for major medical coverage. When I broke my ankle earlier this year and needed surgery, that policy turned out to be a lifesaver. Even with a high deductible, the coverage was robust and far exceeded my expectations.
The moral of the story: great insurance options do exist outside of employer coverage. Just make sure you have experts help you choose the right plan for your needs. When your accounting and insurance decisions are coordinated, you get better protection and fewer surprises at tax time.
4. Payroll and 401(k): paying yourself like a pro
Once my business structure and insurance were set, the next step was setting up payroll to keep my business accounting organized. Waldman Accounting established a system through Gusto that handles salary payments, quarterly taxes, and automatic 401(k) deductions.
Having retirement contributions automatically deducted each month makes saving effortless — and tax-efficient. I’ve been able to maximize my 401(k) contributions, reducing taxable income while investing for the future.
This isn’t a requirement for self-employment, but it was important to me personally. Treating yourself like an employee — with regular payroll, benefits, and retirement planning — legitimizes your business and sets you up for smarter tax planning. Having Waldman Accounting handle the setup was worth every penny for the peace of mind that everything was done correctly.
5. Schedule mid-year check-ins
Self-employment doesn’t mean going it alone. One of the best habits I’ve built is scheduling mid-year check-ins with Waldman Accounting to review:
- Income and business expenses to date
- Estimated tax payments
- Retirement and HSA contributions
- Opportunities to optimize tax planning and reduce my tax bill
These conversations keep me proactive instead of reactive. I always know where my finances stand — and I avoid last-minute scrambles when tax season rolls around.
Closing thought: believe in yourself
Going out on my own has been one of the most rewarding chapters of my professional life. I’ve loved building relationships with my clients and having the freedom to choose projects that excite me. But even more than that, I love knowing that my financial house is in order.
From setting up my LLC and S-Corp to choosing the right insurance and retirement plan, Waldman Accounting has been my guide every step of the way. Their combination of tax planning, insurance expertise, and hands-on business support made a complex process simple.
If you’re thinking about making the leap into self-employment, my advice is: don’t let fear of the financial logistics hold you back. With the right guidance, you can create stability, save on taxes, and build a business — and life — that thrives on your terms.