One Year In: Running Your Own Business is Hard — There Were Tears

Everyone wants to be an entrepreneur. Through circumstances I didn’t choose, I started my business in October of 2017. Running your own business, not as a side hustle but as a pay-the-rent hustle, is a burden and a risk. It’s not all just WiFi on the beach and every romanticized photo you’ve seen on Instagram.

It means being serious. It means being self-aware. It’s not a four hour work day, let alone work week. It takes pride and humility. Discipline and creativity. Blood, sweat, and late nights. And tears. Lots of tears. Seriously. Tears.

The short version of this blog post is that I’m glad I did this but it is hard. It has taxed my ego and self worth and I’m learning to separate those triggers. It’s not personal.

Here are some of the lessons I’ve learned in my first year.

Set Boundaries with Friends and Clients

It’s okay to say no. Saying yes too often eats away at your calendar, billable time, and productivity. Plus, if you’re not setting your boundaries, you’ll be resentful. You don’t want that. As a business owner (and sometimes remote worker), you have control over your time. Take it seriously.

And yes, I’ve told friends that Saturdays (by appointment), I’m available for lunch. It’s completely fine with most people who have day jobs. They’ll understand. If they don’t, then it’s their loss. Protect your time with your boundaries. Be clear. You will have people who will test you. They may say you don’t have a “real job” since you work for yourself. This is even more so with remote work. So I have been practiced but firm.

I’ve told clients I will email them between the hours of 8am and 6pm. That is reasonable. Then, I keep myself to those parameters. Setting boundaries, being self aware, and sticking to them helps you respect yourself and others to also respect your time.

Go to brunch. Enjoy your time off. And try not to look at your phone.

Specialize Your Work and Client Base — Refer the Rest

“Everyone” is not a client. You won’t sync with everyone. Your personality may not be compatible with a potential customer. They might not be the right kind of business for you and, frankly, you may not be able to serve them well.

I’ve turned down a lot of work this year. I don’t do press releases or resumes. I refer that. I don’t do Pinterest. I refer that. Find out what you do well and quickly. Refer the rest.

I rock at Twitter. I don’t do SEO. I write bios, but not white papers.

Say Yes by Saying No

If you do turn down a job or client, do so by referring. Meaning, “I don’t write press releases but Jen Miller does. Here’s her email.” Then you are still a resource and helpful. If you just say no, you look like a jerk. That’s bad branding. Saying no allows you to say yes to the right things.

Instead of wasting your time with the wrong work or the wrong client, spend time on the things that make you money. For me, that’s Twitter. I don’t make money on Instagram.

Experiment with Pricing

You can experiment with pricing. When I first started managing Twitter, I did it for $250 a month. Then I started this business and started at $1,000 as introductory pricing. Now, that same scope is $1,200. I know the market value because I worked at an agency.

I also discount my work for some of my friends. During my WCLAX talk this year, Alex Vasquez asked me what I do about friends who want discounts. I answered by saying a real friend should pay full price. That said, I’ve discounted work for friends who are clients because it’s my business and I can make that decision. But understand why you are making that decision.

For example, I offered a friend a three month trial at 25% discount. I said, “If you don’t see the results you want, we just stop. We’re still friends. No hard feelings. But if we continue, we go to 100%.” It was a fair price and helped us keep our friendship when we ended the account (temporarily, I might add).

Know Your Cost

I spent a long time in construction accounting so this wasn’t a big barrier for me this year. But yeah, $250 a month for Twitter ended up being minimum wage. Know how much you cost yourself to run your business.

When I started, I reverse engineered my salary, then used that as a basis for my pricing. Create a basic budget so you know what your outgoing costs are. This helps you determine a baseline for your pricing.

It’s okay to take a part-time job.

Yeah. In February, I finally admitted. I can’t keep running out of savings or borrowing from family. It’s time to get a part-time job. It was really hard. I felt like a complete failure. In fact, I had to talk to some of my very good friends about my fears and feelings. I felt like the whole world was watching me fail.

Instead, I met new friends. I love my Serbian family and my work doing office work and marketing at the travel agency. And, it’s helped me travel for work!

I’ve been honest with my boss and she gives me flexibility. We’re both trying to run our own businesses. She’s in year 12 and I’m in year 1. But we need other people.

Cash Flow Can Be a Bitch

Oh man. This one is tough. One of my goals for 2019 is to have a fun bank account and a main bank account for bills and business expenses. I learned this tip from my friend  Robert. My biggest issue with cash flow is overly-optimistic projections. So, I had to borrow money from family and friends a few times. It sucks. It’s depressing. I’ve had my BFF hold my hand while I call to ask for help. But they were all glad to help. People like to help you.

Be Honest and Open with Your Peers

When people ask how you’re doing, tell them. Don’t be a complainer, but be honest. I usually say, “I’m good but can be better.” This gives you an opening. People don’t know you’re taking on work unless you tell them. So, if they ask if I have room for clients, I’ll tell them. Currently, I have two openings. I also tweet about it. Almost all of my work has come from Twitter or WordCamps.

Sometimes You Have to Alter Your Business Model

When I first started, a friend reminded me of my previous skills. So, while I was building my client base, I did collections for my friends for a commission.

Be ready for shifts in perception and need. One of the reasons why I love Twitter so much is you can listen to your audience. So one day I saw someone tweet about how much they hate writing their speaker bio. I spontaneously tweeted that I would write a speaker bio for “$25 fast, fast PayPal Cash.” I’ve written over 30 bios and put  my price up to $50.

Build Rest into Your Days

Seriously. I built in the 2:30 nap so much that my dog is trained. When I stop taking 20 minute naps, I get too exhausted. The world won’t stop because you’re unavailable for 20 minutes. I promise. Even if you don’t sleep, lay down, take off your glasses, and close your eyes. You’ll thank me later.

Give Back

Besides being a Make WordPress team rep for the marketing team, I was also a co-organizer for WordCamp Orange County for the second year in a row. I volunteered again for WordCamp Los Angeles, too.

I became a recurring donor for as well as Oxfam and Giving back helps keep your perspective in check.

Keep Up Your Own Site

A cobbler’s children have no shoes is unacceptable. The best way to get work is to do work. As a marketer, keeping up my website and social media profiles is important. These are the results that I can show to prospective clients. You may be asked to give case studies or analytics to prove your worth. It’s not for me to share my client’s stats. Discretion is important. But I can show my own. So I do.

Numbers to Date

  • Written over 800 client tweets.
  • Written over 30 speaker bios.
  • My own Twitter account has over 16000 tweets and 5 million impressions.
  • Two keynotes and 8 WordCamps (two overseas).
  • An average of 24 Meetups attended (2-3 a month).
  • One laptop-less vacation.

I’m at over 1300 words and I feel it’s important to share these, thoughts, especially after the feedback I got on Twitter.

More Thoughts – Speed Round

  • Trust your gut. It’s intuition analyzing data.
  • You don’t have to take every client.
  • Ask friends. Have a close circle you can mastermind with.
  • Publish base pricing on your site. This helps manage expectations.
  • Mix recurring and one-off revenue streams.
  • Make sure your social bios say what you do.
  • Keep business cards with you even when at a bar. Never pass an opportunity.
  • Keep going to conferences. Stay top of mind.
  • Partner with your friends.
  • Your value comes through education.
  • Put expiration dates on your estimates.
  • Put terms on your invoices.
  • Follow up with clients.
  • Rely on tech to make things easier but don’t over-automate. I use Freshbooks and Calendly.
  • Discount if you more work but with an expiration (25% for 3 months).
  • Failure is a good thing. I promise. Learn to accept it. Learn from it.
  • Take job interviews anyway. Learn from them.
  • Email people from LinkedIn asking if they want to outsource. Ask them if they’d rather have a vendor than an employee.
  • Stay teachable.

Looking forward to the next 12 months.

I didn’t want to NOT start my business. If I end up failing, it won’t be because of the fear to start. So, looking forward in the next 12 months, I want to start another bank account and put my “fun money” allowance elsewhere. I also want to seriously consider starting a C-corp and putting myself on a salary through a payroll service. I’d also like to add teaching in my business model. I love that moment when someone gets it and they’re now empowered.


I met Mark Maunder, CEO of  who makes Wordfence

13 responses to “One Year In: Running Your Own Business is Hard — There Were Tears”

  1. So proud of you Bridget, you’re doing awesome! Although, I’m not surprised, I knew you had it in you while you were still doing construction.

  2. This was a very interesting read! Thank you so much for sharing your experience and knowledge. There are aome very valuable insights and takeaways. And last but not least: you rock!

  3. Friend, you could never be a failure. Truth, running your own business is difficult. Times are hard, and it’s only getting harder (to quote a famous poet). A lot of people are taking a step back to regroup. I admire your grit, fortitude, and transparency. It’s only the beginning. Keep going forward. You have many friends that want to see you succeed.

  4. I know for one, you have been my constant cheerleader. There are no words I could come up with that would express my gratitude. Homies stick together.
    Thank you, brother.

  5. Solid GOLD. Wish I’d read it when I started (April 2017, also unceremoniously). There are things jon here I still struggle with sometimes. Thanks for sharing.