Starting a Side Hustle Best Career Advice

It was a cold December day in Cleveland, but my palms and forehead began to sweat. So many times I had waltzed into my boss’ office without a second thought, but on this day it was different. I was almost four years into a job I loved, but I knew I needed to ask for a promotion. The majority of my job growth, I had been informed through some research, was supposed to happen in my 20s, and I didn’t want to get myself stuck. I know I earned this promotion – I worked really hard, I had a list of successes so long I actually rewrote my job description, and I had only gotten great reviews throughout my career. I also knew that my latest request for a promotion wouldn’t come as a surprise, as just one year before at performance review time I submitted a reply with my review explaining how I have been growing with the institution and wished to continue doing so (wink wink). This time, I thought, I am going to be more direct.

When I asked my boss, as suspected, she was not surprised. In fact, she had news for me.

She had spoken to the powers that be, and they said they could not offer me a promotion at this time. That maybe I needed to “grow even more.” I could see in her eyes she felt as defeated as I did. The issue was out of her hands.

Perhaps you could think about exploring activities outside of work that could give you what you might be lacking here, she suggested.

I know the comment was meant well, but in that moment, I was stunned. “Get a hobby? Like go distract myself from this disappointment?” Inside the treadmill of my mind, I started to panic. I felt betrayed, hopeless, and even slightly offended. But at least I had my answer.

Year five rolled around, and I quit my job.

Ten Questions to Ask Your DJ

Ooops, I DJed again.

I started DJing weddings completely by accident. I love music, and I always expected I would be working in some capacity in or with the music industry. First, it was writing, then marketing. But never did I think I’d be making money playing music that I love. Before I knew it, one wedding turned into five, five weddings turned into 10, and now Jody and I DJ roughly between 20-25 a year. If we could commit to the 15 or so events we turn down, this could probably be a full-time job for me.

Those 20-25 weddings happen mostly in the summer: the season in Cleveland when you want to do all of the things. Things I would have a lot easier of a time doing if I didn’t have a side hustle, so needless to say I’ve been experiencing more FOMO than usual. After recently turning down another social event and feeling pretty bummed out (can’t I ever just have some fun?!), I came across a post online yesterday that caught my eye by Catherine Baab-Muguira on called Generation 1099: Millennials are obsessed with side hustles because they’re all we’ve gotThe author details a trend going on in the workforce as of late: more and more people, particularly 20 and 30 somethings, have side jobs that they do in addition to their full time job. I’m one of them, and I’m here to tell you that while sometimes it can suck, yeah, actually it is pretty great. Most of the time.

“Work, work, work, work, work, work”

Not a lot of people can say that the love their day jobs, have autonomy, and get paid what they think they are worth. The odds are, though, is that it can be different when you work for yourself. When you work for yourself on the side, you can have more control. But that doesn’t mean you’ll work any less.

A typical week day goes a little something like this for me: Wake up, work on side-hustle, work out, go to day job, come home from day job, go to a side-hustle related meeting or work on a side-hustle related project from home, hang out with husband, go to bed. And about six months out of the year, you can count on almost every single weekend to be consumed by either one or two DJ gigs, and Jody spending a lot of time working on his wooden wares collection.

It’s insane to think how much time we’ve committed to working. Day job + side job = not much time I’d like for traveling, or relaxing, or spending time with family and friends. (But apparently I can only have three things I actually want – remember Randi Zuckerberg’s dilemma?) However, I don’t believe you can’t have it all – it’s just hard to have it all at the same time.


It’s a blessing and a curse that I love to work. I’m pretty sure that I have the “work your ass off” gene, passed on to me by my father. He came to the United States from Jordan in 1975, worked three jobs in two different cities, surviving on mainly ketchup sandwiches just to be able to pay for his college education. Forty years later, he has put all three of his kids through school, and though he should be retired by now, he’s still running his own business. While I know he’s worked harder than anyone, I’ve always been inspired by his dedication. Doing your own thing, I’m pretty sure, is in my blood.

But don’t get me wrong, I have no intentions of quitting my day job anytime soon. I love writing, I love marketing, I love digital, and I love PR. That is what I get to do at my day job, and I love where I work. And I am so unbelievably grateful that I work at a place for a person who not only knows that I have a side-hustle, but supports me, too. I know that I am really, really lucky.

I also love DJing, and I love being a small part of people’s happiness on their happiest day. And I won’t lie, there’s a huge sense of pride in making more money in five hours working for myself than I do in a week working for someone else. But I know I won’t be doing this forever. (Besides, my Arab dad didn’t eat ketchup to put me through college to be a DJ!) Nevertheless, the experience is and continues to be invaluable. I have expanded my professional skills so much through owning my own side business, and I am able to apply many of those to my job in marketing. Things like building a brand from scratch; word of mouth marketing; closing a sale; accounting; budgeting; relationship building with other business owners; writing a business plan; growing a business; networking; time management; legal stuff; client relations; customer service; curation; consulting; communication; taxes; working closely with your partner without getting a divorce; etc. The list goes on.

Did anything I just listed sound offensive to you? Probably not. Well, none of these skills I would have so deeply learned had my boss not suggested to me to explore other activities in my life during that review. I look back now and wonder how I ever could have felt anything but eternally grateful. It was actually the best career advice I’ve received yet.

A job does not have to define who you are as a person.

Like the Generation 1099 article indicated, many people start their side hustle not just for the money but to gain greater satisfaction in their careers. I want to tell you that in addition to increasing that satisfaction in your profession, you can also develop a greater understanding of yourself. A job does not have to define who you are as a person. I’m Reena. I’m a marketer. I’m a DJ. These labels can change tomorrow. Sometimes I dream about becoming a yoga instructor. Or heading to Europe to write for a magazine. Or moving to Jordan for awhile to be a writer and putting my journalism and Arabic degree to use. Or going back to school to get a master’s degree in psychology. Nothing is off the table if you’re passionate and put yourself first. Our dreams are part of who we are, and certainly no job should keep you from you.

Changing seasons

I try not to think of life as one long event; but like the environment around us, a year in our life has seasons. With a side hustle, you can use some seasons to plan, and some seasons to act. Right now, I’m working a lot, and after this season I’m planning to invest much of that DJ time into more freelance PR and marketing, which I’m deeply passionate about (and I’m sure my father would appreciate a little more!). No, I probably won’t be giving up DJing. It’s just that writing, I know, is what I want I want to do more. With a side hustle, you can give yourself permission to change directions anytime you want.

Do you do, make, write, build, or try something you’re passionate about each day? If not, I’d advocate you try to find or make the time for it. I’m personally a huge fan of early mornings. My mind is most clear then and I have the most uninterrupted time to think, plan, and create for myself before having to give it your all at your day job. If mornings are out of the question, give yourself one hour, one day this week or next to work on something you’re excited about (doesn’t have to be a side-hustle yet!) and pause to reflect upon how it made you feel. Try not to think of it as a distraction like I once started to do, but an enhancement to your life – and maybe even your career. You never know – one day, your passion project just might lead you to your big break.

The Best Career Advice I've Ever Gotten (and That Happens to Be Super Trendy Right Now) #career

DJ Goodwin photo by Lane Baldwin Photography.

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