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10 Failures I’m Grateful For In My First Year Of Entrepreneurship

As I’m moving into my second year of entrepreneurship, I’ve been doing a lot of reflecting on what my first year looked like. Let me tell you, I’ve learned more about myself, business, my relationship and life in this one year than in all my years before this.

Running a business will test your strength, tenacity, and sanity – but if it was easy, then everyone would do it.

Every year around this time I start to get super nostalgic on the year that’s passed and begin to plan for the new year. Since most of social media and online is a highlight reel of people’s lives, I thought I’d share 10 failures from my first year of business and what you can learn from my mistakes.

1. Under charging

Oh boy is this a good one! The first website I ever did I was just so excited that someone wanted to hire me I totally undercharged. I’m talking that when I did the math after everything was done, I was getting paid around $2/hour. Yikes!

Pro tip: Whether you’ve been in business for 1 day, 1 week or 1 month, do the math and know what you’re worth. Just because you’re new, doesn’t mean that your work isn’t high quality!

2. Not following my intuition with a bad client

I got off the phone with this person and had a terrible feeling, but I live in an expensive apartment and I have to eat. Against my intuition, I took the client and yep, you guessed it, it was a total nightmare! I cried to my boyfriend, couldn’t sleep and would work until 10 o’clock at night, until I finally broke up with them, but those few months were so not worth the income I was getting from them

Pro tip: If it doesn’t feel right, don’t do it. Ask yourself, would I hang out with this person outside of work? If the answer is no, then don’t work with them.

3. Not getting a down payment before starting work

For a stint I offered marketing services to clients and after I got off the initial phone call I would send them tons of marketing ideas. I would work on the marketing plan for hours and give an 8-10 page strategy that I planned to implement – all without a single cent. I would send them this without having received a signed contract agreement or anything and I got burned, twice.

I put in hours of work and gave them really valuable information and they took it and ran.

Pro tip: Unfortunately, there are people out there like this, so just to be sure, don’t do a single minute of work without a signed contract and a downpayment for your work.

4. Not putting a limit on the amount of work I could take on

I thought I could do everything all at one time and I was spreading myself so thin that I wasn’t doing quality work. Because of this, I ended up having some very unhappy clients with me. Everything got settled out, but I still feel guilty about those few months where I was not being a responsible business owner.

Pro tip: Know exactly how much work you can take on at once and then schedule out in advance. This way you’re able to spend more time on each client and know your income in the months to come.

5. Getting No’s

I’ve spent tons of hours doing research on potential clients and phone calls with those potential clients, and still gotten no’s. Even if I really really really wanted to work with them and felt the conversation went well, I still got some no’s.

These were huge bummers (and there was more than just one), but they helped to thicken my skin and realize that I won’t be “right” for everyone, even if I think I am.

Pro tip: Don’t stop, don’t get discouraged, keep going. You won’t be the right fit for everyone, but if you know you did your best

6. Not setting boundaries with texting

Getting texts on Saturday night when I’m 3 vodka tonics in about a “small update” to someone’s website is quite honestly, a business owners worst nightmare. When I first started I made it known that I was very available all the time and gave out my phone number. I got texts, picture texts, phone calls at all hours of the night (because I work with people all over the world), and it was so stressful. I was never able to get away from work because I was constantly getting texts.

Pro tip: don’t give out your cell phone number or allow texts. If a client texts you, set the boundaries and reply to them via email. Drink your vodka tonic in peace.


7. Accumulating credit card debt

I literally woke up one day and quit my job. I sort of had freelance clients, but thinking about it now, not really. I had a savings account, but living in Southern California ain’t cheap people, so I started charging my credit card.

It’s not a lot of credit card debt, but it’s debt and it held a cloud over my head for months… especially during slow months. If I were to do it all over again, I would have established my business first (like I didn’t even have a website), and gotten enough clients to pay my rent so I didn’t have to worry about my debt.

Pro tip: Keep your 9-5 and hustle the sh*t out of your side-gig. Treat that side gig as if it’s the only way you’re making money and once you can live off that amount, then consider quitting your 9-5.

8. Thinking people are as genuine as me

I’m an extremely trusting person, which comes with both good parts and bad. The good part is that i’m very open and meet amazing people I might not have met if I was closed off. The downfall, however, is not knowing when to not trust anyone.

Unfortunately, this is a situation that happened to me and as it didn’t affect my business directly, it’s just disappointing.

Pro tip: Listen to your gut and if you don’t like the “vibe”, your intuition is probably right

9. Not prepping for a slow month

There were a few months in 2018 that were really slow and I wasn’t prepared for that. I had a business! And clients! And did good work! So there was no reason for a slow month… wrong. With entrepreneurship comes instability and I wasn’t prepared for the months I had the bare minimum of clients.

I didn’t have a savings account for my business (just a tax account) and was paying myself all the money I was making… MISTAKE. What I know now, is that some money should be put away for taxes and some money should go back into the business and the rest can go to me.

Pro tip: Plan out 3 months in advance and know what you need. Do you need 2 clients to pay the bills and 3 will bring a little extra prosperity? What is your absolute goal? Know exactly the amount so it’s a goal you can work towards each month and months to come.  

10. A failed workshop

In the summer I collaborated with a fellow entrepreneur to put on a workshop. We had all the content and everything set up, but we got zero sign ups. Blame it on the time of year, marketing efforts, or not enough promotion, either way it didn’t happen.

Although this was disappointing, we took what we learned about this workshop not happening, to reframe the curriculum and make it even better for next time!

Pro tip: Really define who your ideal customer is and the curriculum before you put out a course of workshop, this is something we really wish we did!

I hope all of my failures can prevent you from making the same mistakes I did! We’re talking all about entrepreneurship failures on instagram, so make sure to join in on the conversation there!

Hi, I'm Olivia

A designer, brand strategist & life enthusiast with a passion for helping you turn your passion into a purpose-driven business. I design custom brands +  websites for businesses rooted in the health + wellness industry that illuminate their impact online + convert to sales.

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  1. Nicole Victory

    January 12th, 2019 at 1:23 am

    Thanks so much for sharing this! I have absolutely made many of these same mistakes. However, they were learning experiences, which is so valuable. You’re definitely right on trusting your gut with bad clients….it’s NEVER worth it. Happy New Year!

  2. Olivia Sylvestro

    January 30th, 2019 at 4:16 pm

    Yes, so true! I’m so glad that you can connect with this as well. Happy New Year!

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