How to Delegate as a Small Business Owner


Have you ever heard the story about the guy who traded his way up from a red paper clip to an actual house on Hawaii in the span of one year?

Back in 2005 (I’m sooo dating myself here because I just cannot fathom that this went viral over a decade ago), a Canadian blogger named Kyle MacDonald negotiated his way from a single paper clip to a house in only 14 online trades, including a snowmobile and a box truck.

You can read all about it over on One Red Paperclip if you’re curious, but the reason this story came to mind today is because I was thinking about how starting a business is a lot like that paper clip.

It takes a lot of small wins over time to get to the next level. Instead of dealing with paper clips, you trade up by finding your first client, securing your second client, increasing your pricing, collaborating on joint venture webinars, and—this one’s a big one—outsourcing pieces of your business.

When Kyle made that jump from a box truck to a recording contract, it was much like the burst in momentum you’ll make when you hire your first employee and slowly grow it into a team. But a team by itself doesn’t propel your business forward, it requires a leader who knows how and when to delegate.

Out of all the skills you could have as a business owner, delegation is arguably the most important.

Imagine your business as a balloon. You can only blow it up so big before there is no more capacity for growth. Then, you’re going to need another balloon. You can’t do everything alone in your business, so the more successful you are at delegating, the more you can grow your business into something extraordinary.

Delegating doesn’t always come naturally though... it’s hard to let go of control of your baby… especially when you have a very clear vision of what needs to be done.

Personally, I suck at asking for help until I’m literally drowning. (Just ask me about the time I was on a ski lift trying to take a few hours off and literally crying over Slack begging a teammate to take the crushing weight of all these emails off my plate.)


Delegating takes practice, just like any other skill, and the good news is that even if you’re painfully possessive of your work or incredibly uncomfortable asking for help, you can master delegation in a way that works for you. (And believe me, you will be so glad when you do.)

5 tips for successfully delegating as a business owner:

1. Plan ahead.

Finding and hiring the right fit may take some time, so start looking before you’re ready to hire. You’ll have a much better idea of who’s out there, what their skills are, and what you can expect to pay when you’re doing it from a place of stability and not when you’re on the verge of a breakdown (see above—luckily I had Katie waiting in the wings!).

When you do find someone who resonates with you, set up an interview and be sure to ask the right questions to make sure it’s a good fit (for both of you!).


2. Get yourself organized.

If you don’t, you’ll be answering a LOT of questions in the beginning. You want this person’s time to be spent doing the actual work rather than trying to sort through your disorganized task list.

You should expect that there will be questions at the beginning, but if you get your act together ahead of time, you can avoid a lot of stress and rework. After all, if you’re hiring someone to help free up your time, and they are requiring a lot of your time, it kind of defeats the purpose of hiring someone!

You should know exactly what (and how much) you’re delegating and be able clearly communicate the tasks and your expectations before hiring someone.

3. Remember that you will need to devote time in the beginning to train.

Some people think, “Hooray, I’ve hired help!” and throw everything at the person.

Um, newsflash, that’s not going to be a success for your biz and likely won’t make anyone eager to help or work with you.

Instead, take the time to explain your expectations and the job at hand. Give feedback consistently in the beginning to help them improve; it’s so much easier for the person to course-correct now rather than months down the line when they’ve fallen into a rhythm of doing things in a certain way.

4. Get out of your own way.

If you find that your new person isn’t doing things the way you like, the last thing you want to do is take the work back and do it yourself.

First, ask yourself if you’re actually unhappy with the work or if you would rather it done your way. Sometimes, it’s really a matter of letting go of control. If you are really dissatisfied, you need to give the person a chance to right the ship.

This means providing honest feedback as well as being patient to see if the person can put it into action. If it seems like he or she is totally lost, working through it together could be a good option, as long as you’re taking the backseat and encouraging the person to come up with solutions.

5. Give autonomy.

Think back to what attracted you to owning your own business and why you didn’t want to be stuck at a corporate job reporting to someone else. I’m going to guess there’s some element of wanting to be self-directed and the captain of your own ship.

If you’re hiring a contractor or consultant, remember that he or she is also a business owner and likely felt the same way. Even if you’re hiring an actual employee, it’s still a good idea to promote self-management and autonomy with your team.

This not only means avoiding the dreaded micromanagement, but also giving them a sense of having a stake in your business:

  • Share your successes, and thank them for their part.
  • Reward them as much as possible, if you can.
  • Ask for their opinions to show you value their expertise and give them a part in the decision-making process.
  • Welcome and encourage their suggestions and feedback.

Bottom line: be the boss (or client) you’d want to have.

If you had unlimited $$$$ what would you outsource RIGHT NOW? Let me know in the comments.

Download the Non-Disclosure Agreement if you're planning to hire an employee or engage in a joint venture.

How to Get Out of a Business Slump


This is scary to admit but I’m going to tell you the truth.

This past summer, I was in a bit of a slump, business-wise, and from talking to my clients, it appeared to be a bug going around.

For me, a lot of it had to do with The Contract Shop website overhaul. I felt myself holding back on SO many projects because I didn't want to do them twice once we moved over here to Shopify.

If you’re in the wedding industry, you may have noticed your bookings are down, your clients are even more price-wary than usual and Instagram is only giving you 50% of your previous engagement rates...

Ain’t nobody got time for that!

Instead of us all suffering in silence, I want to have a chat about the reality of burn out, slumps, and the not-so-pretty side of being a business owner. 

If you’re feeling kind of slump-y, there’s probably some tell-tale signs... so let’s see if you have them. Symptoms of a slump include taking procrastinating trips to Target’s dollar section (which they’ve conveniently placed at their entrance), signing up for exercise classes (then cancelling that ish when you realize you have to go) and slurping up melting popsicles as “dinner.”

When the hard stuff hits, whether it’s a “friend” copying your every move + platform, or just a general sense of overwhelm quelling your will to put yourself out there, here’s five things you can do to bust out of that slump:

How to find motivation when you're in a business slump

1. Treat yo' self.

Not the traditional self-care, massage-y stuff—that’s way too sophisticated for someone like me who doesn’t even have the patience to color in the lines. As my nephew says, “Uncle ‘Stina, why is your page all pink?” Because choosing complementary colors is too hard at the end of the day, Benny.

The kind of self-care I’m talking about is stuff-your-face-with-Greek-yogurt-popsicles and binge watch that online course you signed up for forever ago. You’re getting something done for your biz and giving yourself a little space to recover from whatever horrifying drama your brain has cooked up that probably will never actually happen.

Are you interested in starting an online shop that sells digital downloads? Click here to join me for a free live masterclass, where I walk you through my sales and lead strategy.

2. Give yourself permission to indulge in a guilty pleasure, free of time constraints.

I don’t mean like, “Tee-hee, I’m not wearing any socks with my sneakers today!” I mean wandering aimlessly in Anthropologie for so long that the cashier starts to wonder whether you’re shoplifting something. If you have a VA, have her field your emails and calls today (a great lesson in delegating) or put up an auto-responder that says your dog is sick. No one questions a sick dog! It’s not worth it to question this and risk hearing about dog barf, anal glands or any of the many other joys of pet ownership.

3. Do something that's productive in a different area of your life.

Return those twelve shirts to H&M that you just *knew* were a bad idea but wanted to work so badly (mid-riffs are perfect for showcasing your pooch, if that’s the look you’re going for). Get your car’s oil changed. Organize your junk drawer. Okay fine, drawers... plural. The point of this exercise is to make you feel like you’re getting somewhere and doing productive tasks, even if all you accomplish is clearing out your DVR of old Bachelor episodes.

4. If it has to do with legal stuff, put a bird on it!

Outsourcing your legal ish is a no-brainer-- you probably didn’t go to law school (smart move!) but I did. So instead of sitting through hours of lectures from your family about how your ‘A’ really should have been an ‘A+’ and that they’re sooOOoo disappointed in you, I’ve gone ahead and done that for you.

Plus, you are already outsourcing like crazy to experts, even if you haven’t hired anyone yet. WATCH ME PROVE IT!

Here’s what you’re already probably outsourcing without even knowing it:

  • Canva for graphic design
  • Tailwind for Pinterest
  • Chipotle for meals
  • Uber for driving
  • Quickbooks for accounting
  • And now, you have The Contract Shop for contracts and website terms + conditions

Just to recap:

Things you should sweat: Whether it’s okay to eat fries and type at the same time lest you risk a greasy keyboard, your wifi connection while you’re “on vacation,” a website that’s down and/or featuring XXX content, sick dog stories and mothers-of-brides.

Things you shouldn’t sweat (aka, let us do the heavy lifting for you): Your client process, whether your biz is legit or if your contract will protect you.


10 Micro Small Business Investments You Can Make Today


It can be a bit overwhelming to balance what you need in order to set yourself up for success with what you can actually afford. It would be amazing to have all the tools and resources you need right from the start of your business, but sometimes you have to make do with what you have available to you.

The challenge is sorting through what is absolutely essential versus what’s a luxury — and then find some really great alternatives to those luxuries for the same or similar results.

There is so much you can do to grow your business with very little.

Just to prove it to you, here’s a list of 10 micro investments you can make in your business today that will save you time, boost your productivity, and/or generate new business.

Note: Some of the links below are affiliate links, which means I may be able to buy myself a cup of coffee if you sign up for these tools... but I have used all of these programs at one point or another and would only recommend tools that I'd use myself!

10 small business tools that cost less than $100

1. Squarespace. If you're just starting out and the thought of creating your own website makes you break down into tears, Squarespace is a lifesaver. Designed for non-techy entrepreneurs, it has so many gorgeous templates to choose from that you can customize without any coding knowledge. If you can click and drag, you can build a beautiful, professional website (with a shopping cart!) with Squarespace. 

2. Books! Resist the temptation to buy online courses and pick up a new book to freshen up your skills and expand your horizons. There are so many great options out there that are just as helpful (if not more so) than an online course, and they’re a fraction of the price. You can even check the library and skip the cost altogether. (Want a few suggestions? Check out my 7 Must-Read Books BEFORE You Buy another Online Course.)

3. Virtual Assistant. If you’re bogged down by administrative tasks that are taking you away from business (like sending your contracts or managing your inbox), hiring a VA is usually an affordable solution. Data entry, paperwork, research, posting to social media — all of these are examples of the little things you could be delegating to a VA that would free you up for more important, business-generating tasks that would be a better use of your time.

4. Canva. If you can't afford a VA or graphic designer, you can get the premium version of Canva. It’s user-friendly, affordable ($12/month), and will save you tons of time with your blog and social graphics. Spend a few hours setting up a template for social media images in advance, and all you’ll have to do is pop in the image and type in your text. They also have so many pretty, predesigned templates that you can customize.

5. Buffer. Buffer is your social media sanity. You can schedule most of your social media using the free version of Buffer (Twitter, Facebook, Instagram, Google+, and LinkedIn), but the Premium version ($10/month) will allow you to schedule 100 posts (versus 10) per platform as well as schedule your pins on Pinterest. The web browser button makes it super quick and easy to pull relevant content to share and schedule as you’re browsing the internet.

6. BoardBooster or Tailwind. Pinterest can be one of the more time-consuming social media platforms, and these tools make managing your boards so much easier. Not only can you schedule your pins, but you can also create campaigns with group boards, test for broken links or duplicate pins, split boards, delete multiple pins in one click, and analyze your performance.

Ima let you finish, but this is one of our best blog posts of all. time. And it relates perfectly to what you're reading right now. So pop it open in a new tab and read it right after this one!!

7. Plann. Does your Instagram feed lack harmony? Plann allows your to visually plan your posts. Just upload your photos and drag them around till your feed looks flawless. You can schedule your posts and their captions in advance, and you can create sets of relevant hashtags for every occasion so they’re always on hand when you post. (If you’re looking for a hands-off solution that posts for you, we’re big fans of Schedugram here.)

8. Stock photography. If photography is not your forté or your focus, you can elevate your brand AND save yourself time by investing in some quality stock photography. Haute Chocolate and KateMaxStock are favorites for gorgeous, modern, and feminine photos for entrepreneurs and creatives.

9. CoSchedule. If you’re a blogger, you’ll love CoSchedule. It allows you to create an editorial calendar, schedule your posts, and schedule social media right from your post drafts. It makes it super easy to make sure your best performing posts are consistently being shared on social media. It syncs with Wordpress, Evernote, Google Docs, and Google Analytics, and it lets you curate content directly from your web browser on Google Chrome.

10. Time. When was the last time you actually looked into your business and thought about what's going well and what's not? It’s really easy to get lost in day-to-day tasks, so it’s a great investment to schedule and set aside time to get strategic about growing your business.

What are your favorite inexpensive tools or money-saving tricks for your business? Share in the comments!

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A list of 10 business & time-saving tools that are less than $100. #smallbusiness #businesstips