Knowing When To Outsource To Help Grow Your Business

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Wedding planner, designer, photographer and creative entrepreneur who helps curate epic events and sparks joy for clients through curated photography art. Let's hang and chat!

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The Top Indicators You’re Ready To Hire Help

Hello, friends! One thing I love the most about being an entrepreneur, is the community of other business owners. I’m truly a believer in community over competition so I wanted to share tips from when I was ready to take my business further in hopes it might help you as well. I am so lucky to be celebrating  5 years of Feathered Arrow, and I have been able to grow an incredible (yet small) team during that time. Figuring out when to outsource has been instrumental for growth in my business. I have even been able to take my business and brand beyond event planning. Did you know that I also offer photography? Also, my brand has grown to hosting community events,podcast called The Local Table (coming soon!), and much more in the works!

No matter where you are in your business, if you’re wondering when to outsource, I wanted to share a few tips so you know when you’re ready! 

Financially Thriving

This is the biggest part of knowing when to outsource tasks in your business. You cannot hire someone if you cannot pay him or her. However, if you’re pricing your product/services properly, you’ll realize if there’s a surplus that will allow you to hire help. Simultaneously, if a future goal of yours is to outsource, see if an increase in price would make that possible. Even if you’re not quite there, I truly believe taking a leap financially will free up your time to do other things for the business. So take a chance and start small. Try cutting back on morning coffee stops and make coffee at home to pay someone else to help you!

When You’re Too Busy

Entrepreneurs often feel they’re so busy working on their business, they don’t get to work in their business. If you’re feeling overwhelmed with to-do’s that you cannot give your clients the attention they deserve, it’s time for help. To get started, write out every single thing you do in a day and how much time each item takes. Is there something you can take off your plate to help you get back on track? This is also a great place to determine what you’re good at and what you’re not so good at. Listen, just because you’re not great at managing finances or blogging weekly, it doesn’t mean you’re not a good business owner. It’s key to know your strengths and your weaknesses because when you know what you’re not good at and really don’t enjoy doing it, that’s where you can start to outsource. I outsource my bookkeeping and my blogging because I know I’m not great at it and I knew someone else could do a better job for me!

When You Procrastinate Certain Tasks

As entrepreneurs, our business is our passion! Our blood, sweat and tears! However, that doesn’t always mean we love every aspect. If every quarter you dread taxes or you struggle to caption every social media post, that’s when to outsource. A professional CPA can help keep your taxes in check. A professional copywriter can help write content. Look at your to-do list for tasks you’re consistently pushing to the end of the list. Again, it’s okay to admit you’re not great at everything. No one is great at every task or aspect of running their business, that’s why companies hire people who have specific skill sets or expertise in certain areas. The same goes for your small business!

When Your Current Environment No Longer Let’s You Thrive

Outsourcing your business doesn’t have to necessarily mean add extra staff. Sometimes what your business needs is a change in scenery. I’ve been lucky enough to recently move Feathered Arrow Events to an office at WeWork and it’s been game changing! Don’t get me wrong, I loved working from home, but having a dedicated office space gives me focus and a professional atmosphere for client meetings. Not to mention, I’ve been able to record my podcast, The Local Table!

Think you’re ready? Here’s a list of staff options to outsource:

  • Part Time or Full Time – The most common depending on your business and your needs but this can be an assistant, executive, etc. 
  • Virtual Assistants (VA’s) – Hiring a VA is a great idea for tasks like inbox management or other remote things. They can help free your time of the day to day tasks that eat up the majority of your time.
  • Independent Contractors – For every wedding I do, I hire on a staff of independent contractors that assist me day of. I’ve even hired an associate planner to help take on other weddings when I am already booked.
  • Specialized Experts – This is for all the lawyers, accountants, CPA’s, etc out there. These are the kind of tasks better left to seasoned professionals but maybe you don’t need their help full time. 

Pro tip: before you hire on a staff member, be sure you’re hiring legally. For example, a full time employee may need benefits and payroll. It’s also a great idea to put in place a contract and NDA for new staff to sign. I know, I know – one more thing to your plate but I promise this step is beyond crucial. You won’t regret the security it will give you and your business. 

I hope this has helped you for your business! If you’re interested to work with Feathered Arrow, click the contact button on my homepage here and let’s set some time to chat! 

Feathered Arrow Signature Kari Dirksen


Expert Party Planner, Podcaster, and Creative Entrepreneur.

I'm a creative entrepreneur at heart and have been running my business for over 10 years and have planned and executed over 150+ weddings. I'm an expert in this industry and care deeply about my clients and making sure they have the best experience. I just launched a podcast with my work wife, Gabby Pinkerton of Cause We Can Events, called Just Another Biz Podcast! Go check it out!

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