9 Suggestions on Exploring Your Side Hustle

I get lots of questions from folks about how I made the leap from working full time (and then some) as Director of Campus Life at Macalester College to working independently. Some of these folks just want to begin doing some speaking and consulting as a side hustle while keeping their full-time role and others want to explore the possibility of moving toward working independently for themselves. It isn’t for everyone but if this is something you are interested in I would suggest you explore it for the learning, the relationships, and the value it can add for your primary employer.

Unfortunately, this is controversial to discuss. I’ve been told directly that it is an off limits topic in student affairs specifically. I think many folks are concerned that their primary employer might question their dedication. This is part of why people are so curious and conversations on closed Facebook groups are vibrant. Since I’ve worked for myself since June of 2015, I feel a bit more freedom than most to discuss this. Here are a few of things I find myself sharing during these conversations again and again.

1. Get a Website Tied to Your Name

A website will be your door to the world. You’ll use it to post content you want to share with others. And others will use it to learn more about you and determine how and if they want to work with you. You don’t want to promote you (your name) AND also promote a brand (company name). Simplify and just promote you. By getting a website that is your name, you also allow yourself the space to shift and change and evolve what you are offering. You may initially be focused on social justice but then decide over time that emotionally intelligent leadership is where your real talents lie. Or you may initially want to do lots of speaking and later find that coaching and online courses are a better fit for you. By having a website that is tied to your name, you don’t have to get a new website as your content evolves.

2. Blog

On your website have a blog. This is a place to share some of your best content in short snippets. It’s also a place to share what you are learning and what you are doing in ways that folks can come back to long after the moment has passed. In many ways your blog becomes a repository of your thinking and ideas. Begin blogging long before you try to make a big push, that way you have a volume of content for folks to peruse. Keep blogging simple. It doesn’t have to be an opus. Just short descriptions of one idea (3 – 5 paragraphs). If I find myself having the same conversation with multiple people about an insight, an idea, a challenge, a resource – then that’s a sign that I need to turn it into a blog post. This post is a good example of that.

3. Cultivate a Social Media Presence

Be thoughtful about the platforms you want to embrace and then be active and engage to build an audience, a reputation, and connections that you can learn with and from over time. For example, I’ve decided to embrace Facebook, Twitter, and LinkedIn. I am on Instagram but I don’t post and only use it for a steady feed of beautiful images of travel, nature, and art. I created a professional Facebook page so that I could unabashedly post content (my own and others) related to my work, without annoying Facebook friends who I assumed had no interest. It has created double duty and sometimes I’m not sure what to post where. Think about what is right for you.

4. Create Great Content and Offer It

Develop your presentation, workshop, coaching, facilitation, content, articles, graphic design, etc. and offer it. Create the kind of content you want to offer and offering it as conference presentations – locally, regionally, or nationally. Offering this content gives you a chance to present, get feedback (about content and presentation), and get better. It also allows folks to learn about what you are learning, creating, and contributing. If folks seek you out, charge but be willing to negotiate. The biggest mistake I see people making is that they are so eager to consult or present that they do it for free, and then they regret or even resent all the work that goes into it. Offer it for a fair price to the clients. If you want to do it for less, offer at your regular price but make it clear you are willing to negotiate for less. If folks negotiate you for less than your “usual fee” they often are very grateful, treat you well, and are willing to offer a glowing testimonial. Ask close friends and colleagues to bring you in and work with their team, lead a training, or facilitate a workshop. If what you have is quality, it should be a win for all involved.

5. Focus on Your Learning

It is an incredible time to be a learner. Books, articles, blogs, TED Talks, online courses, podcast, audiobooks, seminars, social media engagement, conferences, and more. Enjoy the learning for learnings sake and constantly consider how you can integrate what you are learning into the content you want to offer to increase the value for others. Each presentation, site visit, or post is an opportunity to learn. I’ve learned amazing things about organizational change, dining hall structures, parking policies, innovative initiatives on social justice, and unique ways to engage transfer students all when none of those things were related to what I was presenting on during the visit. And each visit should be an opportunity to learn about people and build relationships. Just about every campus visit is a chance to reconnect with someone I knew previously from grad school, a previous job, professional association involvement, or social media. And just about every campus visit brings someone new closer to me as we spend the day or connect. Reconnecting with folks again and making new connections has been one of the most rewarding aspects of speaking and consulting.

6. Ask for Testimonials

Each time you do work ask for assessment, feedback, and a testimonial. These are three different things. The assessment may be more for the client. The feedback is for you and may be formal or informal. The testimonial is for you to share with others who might be interested. Ask for a testimonial on the impact what you did had for the client or their team. Capture these testimonials, ask for an image as well to personalize the testimonial, and ask for permission to share on your site and on social media and tag them if you plan on doing so.

7. Run Your Own Business

Don’t wait until this is your primary job. Even if you are doing this on the side or even if you are making very little or no money, run this like it is a business. That means setting up accounting structures to account for revenue and expenses. Counting business expenses can reduce your revenue and limit or eliminate what you have to pay in taxes. Once you have a business you can count book purchases, conferences, online courses, mileage, office supplies, home office, technology, travel, travel supplies, and more. I would recommend setting up an LLC and getting an employer identification number. I resisted this for a long time because it sounded complicated. When I finally did it, it took me 30 minutes and cost me $50. I wish I would have done it much sooner.

8. Decide Carefully If You Want to Make the Leap

Working for yourself may seem like heaven and complete freedom. It is not. There are certainly upsides and benefits. But there are also downsides and costs to it as well.

People often ask me what it is like to not have a boss. My response: “I have one. It’s me. We have a complicated relationship. We are working on it.”

The lack of salary, benefits, security, stability, and office supplies can all be hard to do without. Think carefully about your ability to manage stress, risk, uncertainty. Think about those around you and who may count on you (a little or a lot) and their ability to manage those things as well. And not making the leap is great too. Having a nice satisfying side business can complement your full-time job greatly. Remember, all the learning I mentioned before? No one benefitted from that learning more than my primary employer. It can be intellectually stimulating, personally rewarding, and professionally engaging. The additional income (especially when your benefits and primary income are managed) can make other pursuits like travel, learning, home projects, and new hobbies possible.

9. If You Decide to Make the Leap – Finish Strong & Plan Your Departure

If you decide to make the leap, don’t announce your departure and begin building your business. Build the business, while fully tending to your full-time job responsibilities. If you check-out of your primary job, you’ll leave people with not so great memories of you. And those people often will be your future clients or will talk with your future clients. You want those folks excited about what comes next for you, not thrilled that you’re gone. Finish strong. Plan your departure at least a year out. When do you want to leave? What do you want to have in place before hand? When do you want to announce? What infrastructure needs to be in place – website, savings, accountant, clients ready to book, benefits?

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Leaders and organizations turn to Keith as an authentic educator, trusted leader, and unconventional scholar helping them advance leadership, learning, and equity.

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