The future of work…aka how do I start an independent consultancy?!

Original publication on Medium.

Alice Walker, an American novelist best known for her book The Color Purple, once wrote, “Look closely at the present you are constructing: it should look like the future you are dreaming.”

Some years ago, I attended a session on the future of food at the Institute for the Future in Palo Alto, where they asked us to consider our relationship to food 20 years ago. Very few Americans were talking about Gluten Free, Vegan, GMO; and when I considered what I was eating 20 years earlier, it was mostly whatever food was left on my (then young) daughters’ plates. This principle of considering the past when thinking about the future has stayed with me. 

So, when it came to making choices about the future of my work, I decided to apply the same idea. In the past, most people had one employer for the entirety of their work life. A lot of the time they even had the same job in that organization, going to work every day and doing that job for years. And then they got a pension, which meant they could retire with financial security. Along the way, their employer gave them job training, withheld and paid their social security, took out monthly taxes, and paid workers compensation and healthcare. These kinds of jobs gave people structure beyond just going to work each day. 

While ruminating on these features of past work, it dawned on me that employers were actually intermediaries for the government, making sure their employees were checking all the required boxes and providing them with social support on a daily basis. 

Today, more and more employers are hiring independent contractors, temporary staff, and freelancers to do specific tasks for them, meaning they are no longer intermediaries providing the services they once did. There’s a huge growth in the number of people who are getting 1099s instead of W-2s. This brings a lot of risk and a lot of potential insecurity to people who are no longer “employees.” They no longer have anyone looking after their social security, taxes, or healthcare, which means they have to do it themselves. What’s more, they don’t have the same social support systems and transparency about career growth.

Enter me—a newly independent contractor trying to figure out how to organize my health insurance, register my business for tax purposes, and generally navigate the back end of setting up a consultancy.

Now, I have to think about things like cash flow. What happens if I land a big contract in August but payment doesn't come in till next January? I will still have to pay my mortgage between now and then. How do I budget for things like this? When do I pay taxes? What are my legal rights? How do I know if a contract I signed makes me liable? How do I connect with other freelancers to make sure I still have a sense of belonging? 

I spent some time searching online for the best tools, apps, and platforms to help me get started, but I ended up just relying on the advice of friends or acquaintances that suggested specific websites to use. For example, I went to LegalZoom to create an LLC and, after I finished setting this up, I wondered whether I should have set up an S Corp instead. I also signed up for apps that manage clients, invoices, and projects as well as allow for credit card payments. But are these the right/best platforms to use? There seem to be so many options but no obvious set of tools that are curated and easy to pick up quickly. 

As I thought about this experience, I questioned whether I should be using online platforms at all, and instead hiring an accountant, lawyer, etc. to help me set up this business. I am definitely predisposed to use the internet because of the so-called “ease” that websites provide, but maybe I should have hired real humans to consult as I walked through the process. 

I realized then that maybe there was an opportunity to redesign these types of services. 

What if we could reimagine the world of independent consulting? What if there was a curated set of tools available as a one-stop shop for setting up a consultancy?

While these are the kinds of questions you might ask a large design consultancy to solve, all independent consultants, freelancers, and temporary staff who are currently going through or have completed this process have the opportunity to share some insights about what has worked best for them. 

As you can see for me, I am still figuring out what works best. I don’t have a strong opinion yet on hiring real people vs. solely using online platforms but I’m starting to wonder whether it might be a combination of those things. While I greatly appreciate the advice my friends and acquaintances have shared, I am beginning to lean in the direction of hiring a few people who have very clear expertise who can point me in the right direction of the most efficient/best apps and platforms to use. 

Are you an independent consultant? Freelancer? Temporary staff member? What are some tools, apps, or platforms you’ve used that have helped you along the way? Who are the kinds of people you have consulted or hired to assist you on your journey of setting up your own business?