• Skip to primary navigation
  • Skip to main content
Collective

Collective

A blog to help freelancers with taxes - Collective

What we offer

Business setup Form your business the right way Accounting Expert approved, powered by AI Invoicing Get paid faster, without the busywork Payroll Payroll made simple for S Corps Taxes Stress-free taxes for solopreneurs Business insurance Coverage for your business Health insurance Instant and affordable health coverage Support Human expertise + AI speed
Pricing Customers
About us Careers We're hiring! Press
Blog Newsletter Webinars

Free tools

S Corp tax savings calculator Estimated tax & extension calculator Tax calendar S Corp admin cost calculator Freelance rate calculator Bill rate calculator
See all free tools →
Login
Business setup Accounting Invoicing Payroll Taxes Business insurance Health insurance Support
Pricing
Customers
About us Careers We're hiring! Press
Blog Newsletter Webinars S Corp tax savings calculator Estimated tax & extension calculator Tax calendar S Corp admin cost calculator Freelance rate calculator Bill rate calculator See all free tools
Login
Resources / Money Management · 7 min read

9 Reflection Questions to Help Your Business Level Up Next Year

Elevate your business in the coming year with 9 reflection questions. Gain insights and strategies for leveling up your success.

woman smiling and writing in her journal. She's wearing a tank top and sitting on the floor of her living room
Sarah Li-Cain
Written by Sarah Li-Cain
Eric Poole
Updated by Eric Poole
Published Dec 8, 2020 · Last updated May 22, 2024
On this page 9 sections
  1. What have I accomplished this year?
  2. What went well and what didn’t?
  3. How have my accomplishments or goals aligned with my business values and mission?
  4. How did my spending have a direct impact on my business goals?
  5. How did I implement work/life balance successfully this year?
  6. Is there anything I need to forgive myself for?
  7. What’s one thing I’m scared of implementing in my business?
  8. What are my priorities for next year?
  9. Who can I seek for outside support to implement my plan?

AI Summary

AI-generated from this article. Not tax advice.

  • Listing accomplishments, no matter how small, is a positive first step in an annual business review.
  • Comparing goals against results specifically helps identify what worked, what held you back, and what actions to take next year.
  • Reviewing how spending affected goals reveals where money delivered a return, such as a Pinterest manager outperforming Facebook ads.
  • Reframing goals as 'priorities' implies choice and can improve mindset and follow-through.

As a busy business owner, you’re probably concerned about looking towards the future. After all, you’ve got a five year plan and all these goals you want to achieve. Before filling up your to-do list in your planner, don’t forget one crucial task: reviewing what has transpired this past year.

I get that it can feel hard to find time to sit down and review what’s happened. However, it’s a crucial activity as a business owner because it’ll help you love your business even more.

Whether it’s maximizing your earnings potential, enjoying more time outside of work or understanding what support you need to have an easier go at entrepreneurship, reviewing what’s happened within the last 12 months will help you get there. That’s because it’ll give you insight into what’s working and what’s not, so you can pivot if need be.

Since each business is unique, I’m not going to suggest a generic way to do your business review. Instead, here are nine questions to help you reflect on the goals you wanted to accomplish, some mindsets to declutter and what you can do to create a vision for the upcoming year.

What have I accomplished this year?

It’s a simple question on the surface, but as you start listing all your business accomplishments, you may surprise yourself at what you’ve done. I know I’m so focused on what I need to do next that I fail to reflect and celebrate all the cool things I’ve completed or opportunities that came my way.

Starting on a high note by celebrating you and your business is a great first step for your annual review. No accomplishment is too small! To start, look back at your calendar and note all the projects and activities that have happened.

Here are some suggestions of things you can write down:

  • All projects you’ve completed for clients (name each one)
  • Each invoice that was paid ahead or on time
  • Every time a client or customer sends you a compliment
  • Whenever you reach or exceed your income goal
  • Paying your quarterly taxes on time
  • Hiring much needed help, like a website redesign
  • Taking vacation time when you said you would
  • Opening a self-employed retirement account

Once you list them out, keep this list because you’ll need it for all the other remaining reflection questions.

Get help setting up your S Corp

What went well and what didn’t?

If you created goals or intentions at the beginning of the year, now’s the time to dig these up and see where you stand. To be clear, this question isn’t meant to make you feel guilty or ashamed if you can’t tick off items in your list. The point is to look objectively at what happened and to see whether these goals are aligned with what you want and to see what may have held you back.

To work through this question, try to be as specific as you can. That way, once you uncover the reasons for what went well and didn’t, it can help to inform what action items you need to take next year.

For example, I wanted to take my exam for my Accredited Financial Counselor (AFC) designation this year. As of December 2020, I have yet to pay for and schedule the exam. Looking back, I had a few family challenges that I ended up prioritizing, plus I am currently volunteering to help in the VITA program, the IRS Volunteer Income Tax Assistance program.

What I learned is that I prioritize my family and I took on too much — studying for the AFC and VITA by itself was a lot. Next year, I will only be scheduling one major activity every quarter, and working on my mindset to be ok with letting work stuff fall by the wayside if my family needs me.

How have my accomplishments or goals aligned with my business values and mission?

Whether you’ve explicitly stated them or not, you have business values — they’re most likely aligned with the personal ones you hold. If you’ve been feeling off about what you’ve been doing in your business this year, it’s most likely that it was because it didn’t align with your values.

Take time to think about what your business values are and what drives your work. Have any of your accomplishments helped you towards them? If so, great! If not, think about the reasons why and figure out how you can change course.

How did my spending have a direct impact on my business goals?

Looking at your spending in terms of goals can help you to be more intentional about where it’s going. Since your business goals are (in theory) aligned with your values, spending money towards your goals means it’s going towards what you value the most.

That being said, not all spending can help you accomplish your goals or live out those values. It’s crucial you look at where your money is going so you can direct it in ways that can have a bigger impact.

Perhaps you wanted to increase sales for a product so you can donate more profits towards a worthwhile cause. You decide to spend a lot of money on Facebook ads to lead potential customers towards it. However, the money you spent didn’t generate enough of a return on investment. Instead, you notice the person you hired to manage your Pinterest account was able to drive lots of traffic to your sales page, leading to a lot more sales.

In this case, the Facebook ads weren’t as effective as your Pinterest manager — guess where your money should go next year?

Thanks to Collective, I don’t have to worry about bookkeeping, taxes and other government related tasks and can focus 100% on my work. If you’re self-employed and need help with tax, bookkeeping and ongoing support, all-in-one place, you’ll love Collective!

Arjun Dev Arora

Strategy, Venture, Technology

How did I implement work/life balance successfully this year?

What’s the point in being your own boss if you can’t take time off? Even if it’s a day off to browse your favorite bookstore or take a nap, you should be able to do it guilt-free. Look at your calendar and see the times where you felt you should have taken time off. How can you ensure you schedule in vacation days next year?

Is there anything I need to forgive myself for?

Forgiveness is powerful in that it releases any negative thoughts you harbor about yourself. Having a better mindset about you and your business is what’s going to help you carve a life you live, so let the past be the past. Sure, you can use what has already happened as lessons learned, but there is no point in feeling bad. What’s done is done — focus on forgiveness and move on.

What’s one thing I’m scared of implementing in my business?

Do you have a big scary goal you wanted to strive for this year but were afraid? Or do you want to finally hire a part-time assistant (and you can afford to) but you’re too much of a control freak? Maybe you’re scared of failure, or it’s too hard to put yourself out there. Whatever the reason is, name it and declare your intentions to the world, or at least tell a few trusted business friends. It might just be the thing you need to kick your behind into gear.

What are my priorities for next year?

Now that you’ve looked at the past, it’s time to use all that knowledge to look towards the future. Instead of calling them goals, think about calling the things you want to accomplish priorities. The word “goals” tends to carry a lot of baggage, like it’s something you have to do. Instead, priorities implies you have a choice.

Plus, this subtle shift can help improve your mindset to something that you want to do and will put at the top of your to-do list instead of feeling overwhelmed at all the things you can implement in your business.

Who can I seek for outside support to implement my plan?

We’re all human — even with the best of intentions we get scared or our schedules get the better of us. Even if you’re super organized, having some form of outside support could help kick your mindset up into high gear and feel better about your business.

Support can come in many forms. Maybe it’s a virtual mastermind group, hiring an accountability coach or a virtual assistant to help you schedule meetings with clients. Start small and look at your budget to see if you can afford this added expense.

Hopefully these reflection questions will help you level up your business and mindset next year. Good luck

Our website contains general information only and this information is not to be taken as legal, tax, or financial advice. You should consult with your attorney and/or tax advisor to get answers to your specific questions.

Get help setting up your S Corp

Collective handles the tax and accounting side of your business – so you have more time to focus on your passion. LLC formation, S Corp election, bookkeeping, monthly financial reporting and an average member tax savings of $10,000*.

Get Started

More on Money Management

All Money Management posts
Blog

S Corp Financial Management: A Plain-Language Guide for Solopreneurs

You set out to do your craft, not to run payroll and chase tax…

Aug 25, 2026 · 7 min read
Money Management

Best Business Bank Accounts for Solopreneurs in 2026

Your business income and your grocery budget don’t belong in the same account. The…

Aug 19, 2026 · 11 min read
Money Management

Payroll Solutions for Solopreneurs: A Comparison Guide

When you make an S Corp election, running payroll becomes part of your required…

Apr 30, 2026 · 4 min read
Blog

How S Corp Owners Navigate Mortgage Approval

One of the most persistent anxieties in self-employment is the mortgage question. Will lenders…

Apr 8, 2026 · 4 min read
Blog

Retirement Plans for S Corp Owners

Intro to Retirement Plans The perks of owning your own business are bountiful but…

Dec 10, 2024 · 2 min read
Blog

What is Payroll?

TL/DR Version Payroll is the process of managing wages, salaries, and taxes for your…

Aug 18, 2023 · 12 min read
Money Management

4 Retirement Savings Options For The Self-Employed

Retirement accounts are important for anyone who wants to retire someday. When you work…

Sep 14, 2021 · 6 min read
Blog

5 Personal Finance Best Practices for Six-Figure Business Owners

You must be doing something right since your business is scaling to the multi-six…

Aug 13, 2021 · 6 min read
Blog

How to Account for Health Insurance, Vacation Time and Other Benefits in your Hourly Rate

The topic of insurance and “benefits” as a full-time freelancer is one that both…

Jun 3, 2021 · 5 min read
Blog

How to Save When You’re Self-Employed and have Inconsistent Income

Dr. Martin Luther King Jr. is believed to be the first to introduce the…

Apr 27, 2021 · 7 min read
Blog

How to pay yourself when you’re self-employed

Payday — these words can sound like music to your ears. After all, you’ve…

Apr 1, 2021 · 6 min read
Blog

How to Run Payroll for an S Corp

You don’t need to be a business with a bunch of employees to run…

Mar 11, 2021 · 4 min read
Blog

How to Use your Personal Financial Identity to Grow your Business

On your self-employed journey, there may be issues and roadblocks that affect the speed…

Feb 2, 2021 · 4 min read
Blog

How the 80/20 Rule Helped me 3x my Revenue in Less than a Year

If you don’t have a finance or accounting background, it may not always be…

Oct 26, 2020 · 5 min read
Blog

How to Create an Authentic Budget for Your Business

When it comes to creating a budget for your business, there’s more than one…

Sep 7, 2020 · 7 min read
Blog

Create a Better Business Using Values-Based Spending

Whether you’re just starting out or have been freelancing for years, the question of…

Aug 31, 2020 · 7 min read
Blog

Level Up Your Freelance Finances with These Expert Tips

When you first started your business, you probably put some effort into your finances.…

May 15, 2019 · 5 min read
Blog

How to Pay Yourself When You’re a Freelancer

Whether you’re first starting out as a freelancer or you’re a self-employed freelancer who’s…

Jan 29, 2019 · 9 min read
Blog

How Much Should You Pay Yourself? S Corp Salary Guide for Freelancers

Many Business-of-One owners with an LLC elect S Corp tax treatment because of the…

Jan 24, 2019 · 14 min read
Blog

How to Open a Business Bank Account for Your New Business

Starting a new business is an exciting time with so much potential in the…

Jul 26, 2018 · 8 min read

About the author

Sarah Li-Cain

Sarah Li-Cain

Sarah Li-Cain, AFC®, is a finance and fintech content marketing writer and strategist with 14 years of experience, writing for outlets and companies including American Express, Investopedia, Intuit, LendingTree, and Bankrate. She's also a podcast producer and host, moderating and producing content for finance and B2B brands.

All articles by Sarah

Best for S Corp owners

Payroll, books and filings in one membership

LLC Tier $199/mo · S Corp Tier $349/mo

Related

  • S Corp Financial Management: A Plain-Language Guide for Solopreneurs
  • Best Business Bank Accounts for Solopreneurs in 2026
  • Payroll Solutions for Solopreneurs: A Comparison Guide

Latest

  • A New Era of Entrepreneurship
  • Collective Raises $100M for Full Stack AI Financial OS Powering the Solopreneur Revolution
  • The Vampire Expenses Draining Your Business

We’re glad you’re here!

First, tell us about your business

Net profit = Total revenue - total expenses

  1. Find total revenue. Add up all money your business earned from sales of goods or services during the year.
  2. Subtract your expenses. Deduct all business costs like supplies, rent, utilities, software, contractor payments, and loan interest.

An estimate is fine, you don't need exact figures.

W2 employees are people on your payroll

You withhold income tax, Social Security, and Medicare from their paychecks, and they get a W-2 form from you at the end of the year.

Don't count yourself (even if you pay yourself a salary) or 1099 contractors and freelancers.

I agree to Collective Terms of Service & Privacy Policy. Additionally, by providing phone number to continue, I agree to receive calls, incl. autodialed or prerecorded sales calls, from Collective.

Collective logo

We are experts in the unique needs and challenges of self-employed people and know that our confidence gives others confidence, too. Reach out to say hello and join our team.

We are experts in the unique needs and challenges of self-employed people and know that our confidence gives others confidence, too. Reach out to say hello and join our team.

Products

  • Business setup
  • Accounting
  • Invoicing
  • Payroll
  • Taxes
  • Business insurance
  • Health insurance
  • Support
  • Late S Corp election

Company

  • Home
  • Pricing
  • About us
  • Careers
  • Contact us

Resources

  • Blog
  • Guides
  • Help center
  • Testimonials
  • Press
  • Create with us

Legal/Support

  • FAQ
  • Terms of service
  • Privacy policy
  • Security policy

Compare

  • Compare all
  • Collective vs Lettuce
  • Collective vs LegalZoom
  • Collective vs TurboTax
  • Collective vs ZenBusiness

Collective provides a suite of tools, back-office support, and general information. Our services are not intended as tax, legal, or professional advice.

* Savings estimates reflect the average 2023 federal self-employment (SE) tax savings for Collective members with an S Corp tax election, based on business profits that would've otherwise been subject to SE tax. Actual savings will vary based on individual circumstances.

** Based on data sourced from Shopify blog, QBO Essentials, QBO Live, Gusto, Taxfyle, Intuit "Tax Pro" Research, LegalZoom and JustAnswer.com as of August 2025.

† Individual tax return packages are billed as an annual, one-time add-on fee.

© 2026 Collective Hub, Inc. All rights reserved