What To Do When You Wear All The Hats In Your Freelance Business

Discover the hats every freelancer and small business owner wears, how to wear multiple hats effectively, and how to take some hats off and get help.

Stacks of freelanace hats

Starting, managing, and growing a freelance business or small business isn’t easy. When you work a traditional job, you only have to worry about your one job because other people handle everything else. But when you start freelancing or start a small business, you’re responsible for everything. You have to fill every role.

You have to wear all of the hats.

Freelancers and small business owners have to learn how to do the jobs of several people just to be in business. They must be flexible and adaptable, have a strong mindset, and juggle each role effectively — otherwise, the business will run then ragged and burn them out.

Sound familiar?

When I started my business, I was a solo freelancer — a solopreneur — blazing my own trail and charting my own path. I wore the overworked badge of honor proudly, well, until I pretty much burned out in a blaze of glory and tried to quit my own business. It was then that I realized…

NO ONE can do it all and business isn’t meant to be done alone, even if you’re a die-hard freelancer or solopreneur.

Over the years, I learned three important lessons:

  1. Asking for help and seeking guidance isn’t a weakness, it’s a strength.
  2. Securing business support doesn’t mean you have to hire. Software can automate a lot of tasks and contractors can be lifesavers.
  3. Hiring subcontractors or outsourcing work doesn’t mean you can’t do it or aren’t good enough to do it.

Wearing all of the hats at first isn’t a bad thing.

It gives you an opportunity to learn about every aspect of your business and better understand each role and its unique responsibilities. This hands-on discovery experience is incredibly valuable because the knowledge you gain will:

  • Demonstrate how you want specific roles to be managed and how you want specific tasks to be done.
  • Guide the development of documented systems and processes.
  • Identify the roles you’ll retain — those that align with your brilliance and genius — and the roles you’ll invite others to fill.
  • Support the creation of specific and clear job descriptions or vendor/partner requirements.
  • Help you confidently hire the right team members and support partners.

Small Business Owners And Freelancers Wear Different Hats

At first, I did everything by myself. I was the accountant and bookkeeper, project manager, account manager, designer, marketer, salesperson, and anything else my business needed. That experience is what helped me learn how to build a profitable, sustainable, freedom-based business that supports my dream lifestyle.

Let’s look at the hats most solopreneurs, freelancers, and small business owners wear…

The Leadership Hat

When wearing the leader hat, you’re the owner, the founder, the CEO, the boss, and the visionary. When it comes to making decisions, the buck stops with you.

Your leadership focus is on:

  • Defining the mission and vision of the business.
  • Deciding what you want the business to be now and in the future
  • Establishing the strategic goals and primary objectives.
  • Managing the other roles within the business.
  • Keeping the business on track and moving in the right direction.

The Marketing Hat

When wearing the marketer hat, you’re in charge of conversions — driving client, customer, lead, and subscriber acquisition. It’s a critical role that can’t be ignored because without clients, customers, leads, and subscribers, there is no business.

Your marketing responsibilities are:

Within this role, there are also several smaller, specialist hats such as: content strategist, content creator, content manager, social media manager, advertising manager, Facebook ads specialist, graphic designer, and video production specialist to name a few.

The Sales Hat

As the marketer, you fill the pipeline with leads, as the salesperson, you must convert those leads to paying clients and customers. When wearing the sales hat, you define and manage the sales process for new clients and customers.

Your sales responsibilities are:

  • Nurturing leads pre-sale and helping them make a buying decision.
  • Going to new business meetings and getting on the phone: hosting discovery calls, strategy calls, and sales calls.
  • Creating proposals, estimates, and contracts.
  • Following up with leads until they make a decision and hire you or buy from you or officially say no.
  • Nurturing client and customer relationships post-engagement to re-engage them for additional work or new purchases.

The Operations Hat

When wearing the operations hat, you’re responsible for managing the day-to-day activities of the business and everything needed for it to run smoothly, which often also includes managing people, workflows, and budgets.

Your operations focus is on:

  • Documenting and managing the standard operating procedures (SOPs) — all the systems and processes that guide the work being done.
  • Ensuring the business is profitable and all practices are sustainable without running it or its people into the ground.
  • Managing vendor, partner, and subcontractor relationships.
  • Determining your packaging and pricing and ensuring you are pricing for profit.

The Financial Hat

When wearing the accountant, bookkeeper, or chief financial offer (CFO) hat, you’re responsible for the money honey and it’s All About The Benjamins. You have to make sure the business earns enough through single sales and recurring revenue to pay expenses, pay salaries and compensation, and return a profit back to the business because if you run out of money, your business is dead in the water.

Your finance and cash flow responsibilities are:

  • Managing accounts payable (money you owe other people) and accounts receivable (money other people owe you).
  • Evaluating and managing expenses.
  • Handling accounting, taxes, and profit reinvestment.
  • Managing salaries, bonuses, and distribution.

The People Hat

When wearing the human relations (HR) hat, you’re responsible for the administrative functions of the business and the people within the business — and yes, this matters even if it’s a company of one and you’re a solopreneur or freelancer.

Your human relations focus is on:

  • Understanding employment law and contracting law.
  • Designing roles, creating benefits packages, and crafting job descriptions.
  • Overseeing the recruiting, interviewing, and hiring of new team members, as well as the firing of team members.
  • Ensuring workplace diversity, equality, and inclusion.
  • Establishing and maintaining workplace culture, creating workplace policies, and setting expectations and boundaries for behavior.
  • Coordinating training and development opportunities.
  • Dealing with people problems, monitoring performance, and resolving conflicts.

The Account Management Hat

When wearing the account manager hat, you’re all about the client or customer. You’re responsible for customer relationships and client management after the sale has been made and the contract is signed. You make sure clients and customers are happy and work to reduce buyer’s remorse, returns/refunds, and bad reviews and increase client retention, customer loyalty, effective hourly rates, and positive reviews.

Your account management responsibilities are:

  • Providing consulting and guiding clients through engagements with care and using client management systems to ensure every client has a consistent, extraordinary experience.
  • Setting expectations and enforcing boundaries.
  • Researching client opportunities, determining the best ways to help clients achieve their goals and objectives, and creating strategies to meet their needs.
  • Fielding requests, answering questions, offering support, providing education, responding to feedback.
  • Managing client contracts, service agreements, scope creep, change orders, and client conflicts.

The Project Management Hat

When wearing the project manager hat, you’re all about coordinating internal resources, managing project scopes, and keeping things on track. You’re responsible for handling the execution of a client or customer strategy and ensuring the delivery of a successful project or extraordinary experience.

Your project management responsibilities are:

  • Creating the project plan that includes the objectives, the timeline and milestones, the resources needed (like people, time, money, and tools), and a step-by-step framework for completing the scope of work.
  • Organizing, coordinating, and overseeing the day-to-day completion of a project’s scope of work and course correcting when needed.
  • Tracking and managing project timelines, budgets, resources, quality assurance, and deliverables to ensure profitability.
  • Seeing projects over the finish line, evaluates team member performance, and provides a documented retrospective.

The success or failure of a project typically rests on your shoulders.

The Production Hat

When wearing the producer hat, you’re responsible for doing the work that was sold. This is when you wear your designer, developer, copywriter, coach, consultant, photographer, virtual assistant, or creator hats. You’re solely focused on fulfilling the promises made to clients and customers and making sure the final deliverables/results exceed their expectations.

Your production focus is on:

  • Doing research, gathering information and context, clarifying requests and requirements, identifying potential options, and testing potential directions.
  • Executing the approved strategy and interpreting and translating client ideas.
  • Collaborating with team members and clients, incorporating feedback, avoiding scope creep, and making revisions to reach the final deliverables or assets outlined.

Wearing Multiple Hats

Some common roles in your business have overlapping responsibilities and objectives, and sometimes you’re the only person filling every role, which means that you often must wear multiple hats at the same time.

For multi-passionate freelancers and solopreneurs who thrive under pressure, wearing several hats at once is invigorating. They love being the go-to person for all things and see it as a great way to engage with a wide variety of interests and skill sets.

The more they’ve got going on and the busier they are the more immersed and happy they are. They do their best work when they’re juggling several roles and are ruthless with boundaries and productivity tactics to ensure they can go all-in on their business and all-in on their rest.

If you can relate, I’m right there with you.

If you don’t want to limit yourself to one thing, that’s okay! Just know that wearing multiple hats doesn’t mean you have to wear every hat.

I like the different challenges of different roles:

  • I like working with clients to take the mess that’s in their heads, turn it into clear brand messaging, and create brand message style guides.
  • I like digging into the visual design of a brand and bringing it to life through color, typography, pattern, imagery, and of course, the logo and identity — and creating the visual brand style guide.
  • I like architecting and designing websites and writing copy.
  • I like developing profitable content structures and paths to cash for content marketers and creating content.
  • I like developing course curriculum, scripts, slide decks, and for some clients, even recording the lessons, webinars, and masterclasses.

All of these things center around strategy and creation — design and content — and they all give me the opportunity to work closely with clients and create transformation.

Keeping a few hats for myself worked because the hats are similar in nature and the context switching isn’t super dramatic. It also worked because I had the right people to fill other roles.

For example, I hired my husband — who was my full-time business partner for nine years — to do everything in the business that didn’t energize me. His main job was to clear things out of my way. He took over all operations, the financials, sales with leads that didn’t know me personally, and the development side of the business.

How To Wear Multiple Hats Without Overwhelm

If you’re a multi-passionate business owner who wants to keep wearing multiple hats, go for it! But be sure to put guardrails in place to protect your time and sanity.

Changing hats takes discipline:

  • Respect each hat and focus on fulfilling the responsibilities of one role at a time. Do not try to multitask. Multitasking means context-switching and that actually damages your brain, makes it harder to focus, and causes tasks to take longer.
  • Use your calendar wisely. Leverage time-blocking to plan specific blocks of time or specific days for specific tasks, and time-batching to group similar tasks and areas of focus together in the same time block.
  • When changing hats and switching between roles, take a break! Stand up, walk around, stretch and move your body, drink some water, or have a snack. This will help you refocus your mind and step into your next role refreshed and reenergized.

If you don’t heed this advice and find yourself with the nagging feeling that you’ve forgotten something, heads up, it’s also caused by multitasking because you’re not focused enough on the roles you’re in.

Wearing Too Many Hats

If you’re not careful, wearing many hats at once can leave you overwhelmed, overworked, exhausted, and on the verge of burnout.

Been there. Done that.

For freelancers and solopreneurs who know their strengths and thrive when their focus is narrow, wearing several hats at once is a nightmare. They love being the visionary, creator, and facilitator of transformation.

They want to do what they do best and let other people handle the rest of the stuff their business requires because they do their best work when fully supported by experts and specialists.

If you can relate, I’m still right there with you.

If you don’t want to wear multiple hats and you only want one perfect-fit hat, go for it! Just know that no longer wearing a hat doesn’t mean you can ignore it.

When you’re a business owner — whether you’re a solopreneur, a freelancer with contractors, or a small business with employees — the buck stops with you. While you odn’t have to be the person in each role, you do have to understand the roles and the associated job duties enough to evaluate performance and quality of work.

Take Off Some Hats And Lighten The Load

If you’re ready to get help and support, start by writing down everything you do in your business and everything you’re responsible for. Then group the tasks and responsibilities you have brainstormed into specific roles.

I know it sounds silly when you’re a company of one, but create an org chart for your business based on the roles identified.

Yes, at first your name will be assigned to every role, but with a visual overview of just how much is resting on your shoulders, you will be able to objectively evaluate each role and consider:

  • The hats you like wearing and feel good in — the roles you enjoy doing.
  • The hats that are old and no longer needed or those can be replaced with newer hats — like software and automation.
  • The hats you don’t like and never really fit right — the roles you don’t enjoy doing.

Once created, your org chart becomes a map of your business and a plan for growing your professional support system and team. It helps you identify the roles to keep for yourself, the roles to fill with other people, and the roles that can be eliminated to simplify operations.

Change won’t happen overnight. Letting go isn’t easy. Choose one hat and start there.

  • Decide if you’ll fill that role with a full-time or part-time employee, a contractor, a vendor/partner, or software.
  • Fill the role and build in time to work out the kinks, figure out workflows, and get everything running smoothly.
  • Then do the same for the second role and so on.

Remember, the roles defined don’t have to be huge roles and hiring help doesn’t have to mean huge commitments. The smaller and more specific the roles are in your org chart, the easier it will be to hire expert support and the smaller your financial commitments will be.

For example, you could hire a designer in several different ways:

  • Develop a relationship with a designer you work with on a project-by-project basis. You’ll pay a little more but you’ll only pay when you need something.
  • Sign a retainer agreement with a design subcontractor who guarantees you a set number of hours every week or month. And yes, there are designers who have retainers as low as five hours per month.
  • Engage a production designer to manage and executive revisions after the initial concept is approved.
  • Hire a specialty designer to only do a specific type of design like social media graphics, blog post featured images, podcast episode artwork, and slide decks.
  • Hire an in-house designer who is solely dedicated to your business.

As the boss, you get to call the shots, which means you get to decide how you hire, who you hire, and what type of support of you want and need.

Team Members With Too Many Hats

When you have a team — employees or contractors — you have to be cognizant of scope creep. Just as a project’s scope can creep out of control, a person’s role and responsibilities can creep out of control.

The longer someone is with you, the more skills they develop, and the more they tend to take on. At first, it’s not a big deal but over time, the pile of hats on their head grows, and eventually, the weight becomes too much.

When team members wear too many hats, it introduces risk:

  • They have trouble managing responsibilities and juggling tasks becomes challenging. That’s when mistakes get made and things start to slip through the cracks.
  • You find yourself relying on one person far too much and that person becomes a single point of failure for your business. If they leave, get sick, or are hit by a bus, you’ll have a huge problem on your hands.

Check in with team members regularly and talk openly and candidly about all the hats they’re wearing and everything they’re doing down to the tiniest of tasks.

You must understand the full scope of their contributions and what your business relies on them for so you can reduce risk and:

  • Make sure they aren’t wearing hats that don’t fit or hats that sort of fit but don’t feel good or look good. There’s a difference between having the ability to do a job and enjoying that job.
  • Confirm they’re the most effective and efficient (and profitable) person to be handling the tasks on their plate rather than the most convenient person.
  • Identify signs of fatigue, exhaustion, frustration, overwhelm, and burnout.

How Many Hats Are You Wearing?

Freelancing and starting, managing, and growing a small business isn’t for the faint of heart. At first, you’ll wear every hat and be responsible for everything — and if you decide to remain a solopreneur, you may always wear a lot of hats.

What’s great about being a business owner is that you get to decide how you want to do business, what you do, and what success looks like.

If you’re intentional and purposeful about how you manage the hats you wear and rotate hats on a consistent basis so one doesn’t wear out faster than the others, you’ll be fine.

Just remember these two things:

  1. No one knows everything so be patient. You will learn new things each and every day — and not just the skills needed to do your job but the skills needed to run a successful business.
  2. No one is perfect so give yourself grace. You won’t be an expert at every role you business requires. You will make mistakes, get yourself into sticky situations, and have some very tough conversations.

Luckily, you don’t have to do it alone.

Being a part of a tight-knit mastermind group, a training and mentorship program, or a niche community can not only provide valuable insights, support, and fresh perspectives but also the opportunity to tap into the experience and expertise of others and benefit from their lessons learned — and that can help you wear all the hats like a total pro.

Be a better freelancer and build a better business by not going at it alone. As the proverbs says, let’s go father together.

While you’re here, I hope you’ll check out:

  • Profitable Project Plan, a business training and mentorship program for freelancers and small business owners with lifetime access and participation.
  • Content Creators Club, a monthly membership that provides direct support with content strategy, copywriting, copyediting, and content creation.
  • Content Camp, done with you workshops on brand messaging, website copy, and content marketing with lifetime access and participation.
  • Seeking Satisfaction Extra Minutes, a monthly membership that provides weekly business training from me and podcast guests in 25 minutes or less.

Every program has a live component where you’ll have the opportunity interact and engage with me and other members to build new relationships and get direct, actionable feedback. I’d love to have you.