When to Go Solo: It’s Not About Having Your Sh*t Together

Career Development

One of the most common questions I get is: when did you know it was time to let go of the steady paycheck and “go solo?” I think the reason this question comes up so often is because there is no one-size-fits-all answer.

My story certainly didn’t follow commonly given advice.

  • I didn’t have a business plan.
  • I didn’t make a dime through W&D for five years.
  • I didn’t have more than a couple of hundred bucks in my savings account.
  • I had credit card debt.
  • I didn’t know if I wanted W&D to be a blog or a design studio.

On paper, I didn’t appear ready to make the leap into full-time freelance, but my gut told me it was time. Since I didn’t have the luxury of money or time, I started to think about what I had going for me. I had the energy and was focused on putting in the extra hours. I was willing to fall flat on my face and go back to designing at an agency. I was willing to work a couple of odd jobs if I needed the money. I knew I couldn’t spend another year building brands for other people and not explore what W&D could be. I decided I wanted it too much and was willing to work hard to make it work.

I didn’t know it at the time, but this was my first exercise in assessing risk. I had taken stock of the potential pitfalls, thought about the probabilities associated with them, and considered the likelihood of the worst-case scenario playing out.

My last paycheck was March 2014.

I put together a list of attributes I think help assess your readiness for freelance life, even if you haven’t got your ducks in a row.

1. You’re willing to work more than 40 hours a week.
When you’re freelance, you’re not only the boss, but you’re also the accountant, janitor, receptionist, and project manager. All these roles add up to much more than a 40 hour a week job. The good news is you get to choose when you log these hours. For me, I keep a 8:30-5:30 schedule and pick back up again at 9 pm. I’ll work until 11 pm on a good night, and 2-4 am on a bad night. There’s often a chunk of time set aside to work on the weekends, too.

One important note: you can’t keep up an 80 hour a week pace for long. Entrepreneurs need rest and downtime to recharge, and it’s even more important for you to stay healthy because if you’re out of commission, your business may be compromised.

2. You’ve got a back-up plan for your back-up plan.
I was once told that your worst-case scenario shouldn’t happen unless four things occur in succession. The likelihood of that happening is small, so if one or two things go wrong, you’re not in emergency mode. What I like about this approach is it makes it possible for you to have multiple backup plans. I have a list of things I’d need to do to make sure my family and my savings are secure before turning towards a credit line or dipping into our savings account. The risk is very real, and I think about it every night before bed, but it helps knowing I have my plan in place.

3. You’re comfortable being uncomfortable.
Worrying that people won’t hire you never goes away. Worrying about having enough money in your savings account to cover taxes never goes away. Even as your business grows, your problems become more complicated. If you’re comfortable with discomfort, you’re going to do well on your own.

4. You’re OK doing work you don’t love.
There’s a lot about being a boss that isn’t fun. Quarterly taxes, 1099s, receipts, lawyers, Quickbooks— all of these things are the last thing I want to spend my time doing. But knowing your numbers, knowing your P&L, and by understanding the basics of business tax, you’re able to make smarter, more strategic decisions, especially when you’re close to the financial health of your business. My point is, running your own company is far from spending your days doing what you’re passionate about. Instead, you’ll find yourself making time outside of business hours to focus on doing the thing that inspired you to go solo in the first place.

5. You’re OK with criticism.
When you’re the boss, you’re responsible for everything that happens with your business. Criticism is essential and imperative to evolving and reinventing your business as you learn more about your customers and what you’re offering them. All this said it’s important to be able to identify constructive criticism from people who doubt or don’t understand your vision. Knowing when to take advice or leave it is just as important as being open to hearing feedback.

6. You’d regret not giving it a go.
When all is said and done, regret sticks with you for a long time. It follows you to your next job and for decades to come. Failing as a freelancer doesn’t mean your career is over. You can always get a full-time job. The point is, if you want something, there’s less to lose than you may think.

Regret. That’s what pushed me over the edge. Three years after my first month without a steady paycheck, the business hasn’t become more streamlined. In fact, we’ve added events and product development to our capabilities. I still don’t have a business plan. I often joke that if I went on Shark Tank, I’d be chased out of the building for spending too much time working on things that don’t make us money or for not focusing on one area of our business.

These days, I try not to focus on what we’re lacking, but where there’s a little bit of magic happening. We put things out into the world and listen to what people say, then take the result and spin it into the next iteration. Sometimes the things I work hard on fall flat and the things I put barely any thought behind catch on quickly. There’s not a science to building something, despite what the analytics and data might tell you.

Numbers are important but remember never to underestimate what grit and passion can make. Going solo is betting on yourself.


If you’re interested in chatting more about launching your own business and live near the Minneapolis area, sign-up for my breakfast on Thursday, May 18 from 7:30 – 9:30 am at Studio 125, where I will answer questions and discuss starting a small business, social media, branding, blogging and more. Sign-up and get all the details here! Breakfast with Kate of Wit & Delight.

Image from Piccsy.com

BY Kate Arends - March 28, 2017

Inline Feedbacks
View all comments

Your posts on freelancing and starting a business have helped me lots. I’m glad you decided to trust your gut and to start W&D… otherwise I wouldn’t be reading such great tips!

Charmaine Ng | Architecture & Lifestyle Blog

March 28, 2017 5:29 pm

Thank you for the honesty in this. There is no perfect time to go solo, I’m slowly learning that. While I’m still not quite ready (mentally and financially) to take that leap, your words have been a real inspiration


March 29, 2017 3:49 am

This resonates with me so much! I have been flying solo for about 5 months now, not making any money as of yet and I get so stressed about it, but reading about your own experience with freelance helped me relax. Just a tiny bit. 🙂
Thank you!

March 29, 2017 6:34 am

Another fantastic post, Kate – Wit & Delight is smashing it with content these past couple of months, I regularly check back to see what you’ve published! 🙂

Flora x

March 29, 2017 8:34 am

As always, a very good article. I like your honesty and your relevant advices. Thanks!

March 30, 2017 12:17 pm

Numbers 3, 4, and 5 are things I’ve had to come to terms with being a new business owner. But even though accounting is never fun, tracking my expenses and income kinda feels like I’m tracking my success. So when I look at it that way, it’s a bit more fun and interesting to do! Albeit, still not something I eagerly look forward to lol.

April 5, 2017 8:25 am

Refreshing & inspirational post – as ever!
From another girl ‘giving it a crack’ on my own, THANKYOU Kate

Jen G
March 9, 2018 6:05 pm

Thank you, Kate! I am thinking of making the solo leap myself in an area that most small business owners don’t enjoy, such as yourself… accounting. You and I worked together in a past life and I probably processed you’re last paycheck. :). I am planning on attending the breakfast that you’re hosting!

March 14, 2018 9:31 pm

Loved the article – super insightful and helpful!

I would love to attend the breakfast on May 18th – I clicked the link but the page wasn’t found. Is there another way to register for the breakfast? Thanks in advance for your help!

Most-read posts:

Did you know W&D now has a resource library of  Printable Art, Templates, Freebies, and more?

take me there 

Arrow Alone

Get Our Best W&D Resources

for designing a life well-lived


Arrow Alone

the latest

Thank you for being here. For being open to enjoying life’s simple pleasures and looking inward to understand yourself, your neighbors, and your fellow humans! I’m looking forward to chatting with you.

Hi, I'm Kate. Welcome to my happy place.











follow us on instagram @witanddelight_