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Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media
Side Hustle Pro
Latest episode

518 episodes

  • Side Hustle Pro

    510: How I'm Rebuilding After A Hard Season (feat. Monique Shields)

    2026/04/17 | 49 mins.
    In this episode, I’m joined again by Monique Shields, and this conversation felt like therapy, coaching, and truth-telling all in one. We went deep into something I’ve personally been navigating: what it actually looks like to move out of survival mode as a high-achieving woman, especially when life has been life-ing.

    We talked about the invisible weight many of us carry, from parenting to business to unexpected life challenges, and how that impacts the way we show up, make decisions, and even spend money. One of the biggest shifts for me? Realizing I wasn’t telling myself the full story about what I had been carrying and surviving.

    Monique breaks down how our mindset around scarcity, energy, and outsourcing can keep us stuck, and what it really means to “resource yourself” instead of just pushing through. If you’ve been feeling stuck, foggy, or like you’re doing everything but still not moving forward, this episode will hit home.

    Main Takeaways
    You’re not behind, you’re likely operating without acknowledging everything you’ve been carrying
    Scarcity mindset after a hard season can quietly shape your decisions and keep you stuck
    Your energy, not just your time, is one of your most valuable assets
    Resourcing yourself (mentally, physically, strategically) is essential for growth

    Highlights Include
    00:00 – Reconnecting with Monique and what she’s been building
    02:30 – Why intimate spaces and coaching containers matter
    04:30 – Starting YouTube and breaking through creative burnout
    06:00 – The hidden impact of hard seasons on decision-making
    08:00 – Why you’re not telling yourself the full story
    10:00 – High-achievers and the trap of self-pressure
    12:30 – Why “feeling less overwhelmed” isn’t the right goal
    15:00 – Scarcity mindset after financial or life shocks
    18:00 – Why cost-first thinking keeps you stuck
    21:00 – The “delusional belief” successful people hold about their future
    27:00 – The real value of your time and energy
    33:30 – What actually changed after hiring support
    36:00 – Mental fog and why you don’t even realize you’re in it
    40:00 – Why stability is not the same as hoarding
    43:00 – What it really means to “resource yourself”
    46:00 – The importance of having multiple “brains” supporting you
    50:00 – Why your nervous system needs support in today’s world
    52:00 – Reframing “I can’t afford it” into a choice

    Links Mentioned in This Episode
    Save the Date: Start the Podcast That Builds Your Exit Plan (April 17)

    Watch & Listen
    Watch this episode on YouTube and listen on all podcast platforms:
    Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    YouTube: https://www.youtube.com/sidehustlepro

    Announcements
    If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan
    Save your seat here.

    Social Media
    Instagram: @moniquershields
    Podcast: Ambition Without Compromise

    Side Hustle Pro – @sidehustlepro
    #SideHustlePro
    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle Pro

    509: Opening Up About My Journey as an Autism Mom

    2026/04/10 | 32 mins.
    This episode is one of the most personal and vulnerable conversations I’ve ever shared. I’m opening up about my journey as an autism mom, from the early days of pregnancy and motherhood during the pandemic to navigating the realities of developmental delays, diagnoses, and advocacy.

    What started as subtle concerns about speech delays turned into a life-changing journey through early intervention, therapy, and eventually receiving an official autism diagnosis for my son. Along the way, I’ve had to learn how to advocate fiercely, navigate complex systems, and redefine what motherhood looks like for me and my family.

    This episode is about the hard moments, the emotional weight, and the unexpected beauty in this journey. It’s also about community, resilience, and learning to see strength in a path that looks different than what I once imagined.

    Highlights Include
    00:00 – Why this episode is deeply personal
    02:00 – Pregnancy, birth, and early milestones during the pandemic
    04:30 – First signs of speech delay and comparing developmental milestones
    06:30 – The emotional impact of early evaluations
    07:30 – Starting early intervention: speech and occupational therapy
    09:00 – Transition to specialized preschool and navigating the system
    11:00 – The hidden challenges of parenting a child with special needs
    12:30 – Communication barriers and emotional regulation as a parent
    14:00 – The moment I realized how much I’ve been carrying
    16:40 – Understanding gestalt language processing
    19:30 – Getting an official autism diagnosis
    21:00 – Advocating for my son within the school system
    23:30 – A “guardian angel” moment that changed everything
    27:00 – The role of faith in navigating this journey
    29:00 – Finding community and learning from other moms
    30:30 – Lessons autism has taught me about boundaries and perspective
    31:00 – A real-life parenting moment at the barbershop
    33:00 – Choosing celebration during Autism Awareness Month

    Links Mentioned in This Episode
    • Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 17)

    Watch & Listen
    Watch this episode on YouTube and listen on all podcast platforms:
    Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    YouTube: https://www.youtube.com/sidehustlepro

    Announcements
    If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan
    Save your seat here.

    Social Media
    Side Hustle Pro – @sidehustlepro
    #SideHustlePro

    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle Pro

    508: The Tax Mistakes Side Hustlers Make That Cost Them Thousands (And How to Avoid Them)

    2026/04/08 | 34 mins.
    If you’re a side hustler or solopreneur, taxes can go from simple to overwhelming real fast and the truth is, many entrepreneurs are quietly losing thousands of dollars just by not knowing what they don’t know.

    In this episode, I sat down with CPA and TurboTax Expert Lisa Greene-Lewis to break down the most common tax mistakes side hustlers make, from choosing the wrong business structure too early to missing out on key deductions and failing to stay organized throughout the year. We also unpack what actually makes taxes more complex as your business grows and how to stay ahead of it before tax season hits.

    This conversation is all about helping you feel more confident, more prepared, and more in control of your finances. Because the goal is not just to make money in your business but to keep more of it.

    Main Takeaways
    Lack of consistent tracking is the biggest mistake that leads to overpaying taxes
    Many solopreneurs miss deductions simply because they are unaware of what qualifies
    Staying organized year-round is the key to reducing stress and maximizing savings

    Highlights Include
    00:00 – Introduction to tax season for solopreneurs
    02:00 – Lisa’s journey into tax expertise and entrepreneurship
    05:20 – LLC vs S corp: what you actually need to know
    08:20 – When taxes start to feel complicated
    09:30 – Why tracking income and expenses is critical
    11:40 – Common deductions people miss
    13:00 – Home office deduction explained
    14:20 – Section 179 and equipment write-offs
    15:10 – What you can’t deduct (clothes, hair, makeup)
    16:40 – Business credit card interest deduction
    17:20 – Employing your kids as a tax strategy
    18:00 – SEP IRA and retirement savings for entrepreneurs
    19:00 – Qualified Business Income deduction
    20:10 – Key tax law updates and 1099-K changes
    23:20 – How to stay organized with QuickBooks
    25:40 – How TurboTax experts support business owners
    27:10 – Lisa’s personal system for staying organized

    Links Mentioned in This Episode
    TurboTax: https://turbotax.com/business
    QuickBooks: https://quickbooks.intuit.com

    Watch & Listen
    Watch this episode on YouTube and listen on all podcast platforms:
    Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    YouTube: https://www.youtube.com/sidehustlepro

    Announcements
    If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan
    Save your seat here.

    Social Media
    LinkedIn: https://www.linkedin.com/in/lisa-greene-lewis-7721b815a
    Website: https://turbotax.com/business

    Side Hustle Pro – @sidehustlepro
    #SideHustlePro
    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle Pro

    507: The Hidden Cost of Waiting Until You're Ready

    2026/03/27 | 28 mins.
    If you’ve been waiting for the perfect moment to finally start that thing you said you’d do this year, this episode is your wake-up call. Because the truth is, that moment isn’t coming.

    This week, I’m pulling back the curtain on a very real, very messy week in my life and sharing why I decided to hit record anyway. From sick kids to mental clutter to a house that is far from organized, I had every reason to wait. But instead, I leaned into a powerful reminder: progress doesn’t require perfection.

    In this episode, I walk you through the mindset shifts that have helped me move through overwhelm, take action with limited time and energy, and stop letting the idea of “feeling ready” delay my goals. Because sometimes the real work isn’t the task itself, it’s learning how to show up before everything feels aligned.

    Main Takeaways
    Waiting for the perfect time will keep you stuck longer than just starting messy
    You have to work with the time and energy you actually have, not what you wish you had
    Naming what’s holding you back helps you move through it faster
    The real growth often comes from managing your mindset, not completing the task

    Highlights Include
    00:00 – Why I recorded this episode despite not feeling ready

    02:10 – How “unexpected” life moments keep disrupting plans

    04:18 – Learning to work in chaos instead of waiting for order

    05:30 – Lowering the bar to get started

    06:10 – Work with the time you have, not the time you wish you had

    08:00 – Managing your energy to show up at your best

    10:15 – Why naming the problem helps you move forward

    11:43 – Recognizing the season you’re in and adjusting expectations

    14:00 – Are you truly blocked or just thrown off?

    16:12 – How accountability helped me launch Side Hustle Pro

    18:36 – Overcoming imposter syndrome in a career leap

    21:22 – The hidden cost of needing to “have it all together”

    23:21 – Why perfection delays your income and growth

    26:24 – Maybe the real goal is mastering your mindset

    29:19 – Adjusting expectations so you can move forward

    Links Mentioned in This Episode
    Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 10th)

    Watch & Listen
    Watch this episode on YouTube and listen on all podcast platforms:
    Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    YouTube: https://www.youtube.com/sidehustlepro

    Announcements
    If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan
    Save your seat here.

    Social Media
    Side Hustle Pro – @sidehustlepro
    #SideHustlePro
    Hosted on Acast. See acast.com/privacy for more information.
  • Side Hustle Pro

    506: 5 Simple Ways to Get Paid for What You Already Know

    2026/03/20 | 23 mins.
    One of the biggest misconceptions I see when it comes to making money is the belief that you need to start from scratch. A new certification, a brand new idea, or a completely different skill set. But the truth is, most of us already have everything we need. The real problem is not a lack of knowledge, it is not knowing how to package and position what we already know.

    In this episode, I break down five simple and practical ways to turn your existing skills, experiences, and knowledge into income. Whether you are in between roles, exploring a side hustle, or just trying to make extra money right now, this episode is your reminder that there is value in what you already bring to the table.

    I also walk through a key mindset shift. You do not need to be the top expert. You just need to be a few steps ahead of the person you are helping. People are not just paying for information. They are paying for clarity, speed, guidance, and confidence. And that is where your opportunity lies.

    Main Takeaways
    You do not need new skills or certifications to start making money
    There are five core ways to monetize what you already know
    People pay for clarity, speed, and guidance, not just expertise
    Start with one path and keep it simple instead of trying everything

    Highlights Include
    00:00 – The biggest misconception about making money
    01:30 – Why you already have valuable, monetizable knowledge
    02:00 – The 5 ways to make money with what you know
    03:00 – The mindset shift you need before starting
    04:00 – Service and coaching as the fastest path to income
    06:00 – Done-for-you services and why people pay for convenience
    08:00 – Creating simple digital products that sell
    10:30 – Workshops and why people pay for real-time learning
    13:00 – Why reminders are key when selling anything
    15:00 – Using content to create opportunities and income
    18:00 – How to use AI without losing your voice
    21:00 – Why you should pick ONE path and start now

    Links Mentioned in This Episode
    Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, March 20)

    Watch & Listen
    Watch this episode on YouTube and listen on all podcast platforms:
    Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
    Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    YouTube: https://www.youtube.com/sidehustlepro

    Announcements
    If you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit Plan
    Save your seat here.

    Social Media
    Side Hustle Pro – @sidehustlepro
    #SideHustlePro
    Hosted on Acast. See acast.com/privacy for more information.

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About Side Hustle Pro

Side Hustle Pro spotlights bold black women entrepreneurs who have scaled from side hustle to profitable business. Join Chief Side Hustler turned full-time entrepreneur Nicaila Matthews Okome for your weekly installment of Side Hustle Pro and learn actionable strategies to start small and get going–wherever and whoever you are. Side Hustle Pro features interviews with inspiring Black women entrepreneurs who started out as side hustlers, including interviews with Myleik Teele, Morgan DeBaun, Tiffany "The Budgetnista" Aliche, and more! Hosted on Acast. See acast.com/privacy for more information.
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