Young Upstarts

All about entrepreneurship, intrapreneurship, ideas, innovation, and small business.

How To Start A Second Side Hustle

Have you ever sat down at your 9 to 5 job and wondered if this is all there is? Like many people, you have a wide range of passions that don’t fit neatly into just one career. This is where starting a side hustle comes in. It isn’t just about making extra money, although that’s a huge perk. Side hustles are also about exploring your interests. With a little luck and a lot of hard work, they might also grow to become your main source of income.

According to a report from, 44 million Americans have a side hustle. More Millennials than any other group have embraced this new moneymaking option. However, people of every generation have found success with their side hustle. In fact, 36% of people working a side job earn an extra $500 a month. Now that’s something to think about. This could be enough to cover part of your rent, build your retirement nest egg, or make a serious dent in your loans.

There are no guarantees for success. However, here are five smart principles that can help put you on the right path:

1. Don’t Rush It.

Starting a side hustle can be exciting. It’s easy to get a little carried away and go full steam ahead. However, this could end up being an expensive mistake. When first starting these ventures, you have a lot to learn about what the market wants and what equipment you’ll need. Starting small scale means that if you ruin an entire batch of experimental cupcakes, you aren’t out hundreds of dollars.

What if you’re presented with an opportunity to grow your business fast? This sounds like a dream come true for many people, but put some serious thought into it before saying yes. Large scale means larger demands on your time and possibly expensive new equipment or space. If Shark Tank has proved anything, it’s that sometimes going big time ruins the small hustle.

2. Be Careful Who You Work With.

If you’re starting a side hustle, you may think that partnering up or getting an investor is a good choice. This makes sense on the surface. After all, you’ll get another set of hands and extra resources. However, even partnerships between spouses or good friends can sour over time, especially when there’s money involved. Put careful thought into this decision. Remember that having a partner will leave you with less than 100% control of your business. Are you okay with that?

Also, don’t neglect getting a fair and ironclad contract. It’s important to include in writing how you will dissolve the partnership if one of you decides this venture isn’t the right fit and wants to leave.

3. Success Takes Time.

Even with such a passionate person as yourself at the helm, your side business may need some time to grow into its full potential. Depending on what the hustle is, you may need to:

  • Bargain with distributors
  • Build a social media platform
  • Arrange insurance for your business
  • Attend trade shows and events to promote your services
  • Pitch ideas to clients
  • Create an advertising campaign
  • Develop and release products

For some people, their weekends are devoted to the new job. Others carve out an hour a day. Before you commit to this hustle and start buying equipment, write out your weekly schedule. Do you have enough free time? If not, can you make enough free time?

4. It’s Not About the Destination.

Although you have big dreams for your side hustle, you may be on a long road to get there. There will be ups and down as the economy shifts, customer tastes change, or a supplier falls through. Success may take longer than you hope, but that’s okay. You started this side job to explore your passions. Let that passion carry you through the day. The enthusiasm you bring to your business will shine through in your products and customers’ experience.

5. Stay Agile.

Only one thing is for sure: the future is going to throw you some curveballs. The great thing about being an entrepreneur who runs a one-man business is that you can think on your feet. You have the flexibility to make any decision that you want when the unexpected happens. This means that you can take advantage of opportunities that crop up and pivot your hustle quickly to deal with a changing marketplace. Your flexibility and ingenuity are some of your greatest strengths as you grow this side venture.

Hustles For Every Personality.

Are you looking for high paying side hustles or side jobs for creative people?¬† Whether you’re artsy, love animals, or have the driving skills of a Hollywood stuntman, there’s something on this list for everyone:

For social butterflies:

Consider joining Postmates, Uber, or Lyft and you’ll get to know the ins and outs of your town. Places like Edmonton have made it easy for anyone to join the rideshare economy, provided you get adequate car insurance in Edmonton.

For people who love animals:

Advertise your services as a dog walker or pet sitter and hang out with adorable pups all day.

For creative people:

Throw an ad onto Fiverr where you can do everything from designing logos to singing YouTube channel jingles.

For people who’ve had a lot of jobs:

Resume coaches help others whip their work history into shape.

For people who know their way around social media:

Consider becoming a social media manager and bringing the magic to other people’s social media profiles

For people who love shopping:

Become a personal shopper and you can have all the fun of hitting the stores on someone else’s dime.

Side Hustles Can Be Your Main Passion.

‘Passion’ got mentioned a lot in this article. That’s because whatever you want to do in your free time, whether it’s dog walking or jingle writing, your passion will make your small business shine. It can carry you through tough times and bad luck. With a side of good judgment (think carefully before you make that partnership or buy that expensive equipment!), you can turn a lifelong dream into your dream career.


Young Upstarts is a business and technology blog that champions new ideas, innovation and entrepreneurship. It focuses on highlighting young people and small businesses, celebrating their vision and role in changing the world with their ideas, products and services.

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