Ogunnaike memulai karirnyakariernya di bidang jurnalisme pada 1999 dengan meliput berita hiburan dan budaya pop. Dia adalah reporter untuk The New York Times dan memimpin liputan hiburannya, dengan fokus pada selebriti seperti Jennifer Lopez, Ozwald Boateng, Oprah Winfrey. Ia juga menulis untuk bagian "''Arts and Leisure''" di koran tersebut. Dia adalah penulis untuk majalah Vibe, berkontribusi pada fitur musik bulanan dan cerita sampul. Karyanya juga telah diterbitkan di Rolling Stone, New York, Glamour, Detail (majalah), Nylon, New York Observer dan V Magazine. Dia juga menemani dan mewawancarai Michelle Obama dalam tur ke Afrika Selatan.<ref>{{Cite web|url=https://www.vibe.com/2011/08/vibe-veteran-lola-ogunnaike-speaks-interviewing-michelle-obama-africa|title=VIBE Veteran Lola Ogunnaike Speaks On Interviewing Michelle Obama In Africa|date=2011-08-26|website=Vibe|language=en|access-date=2020-05-09}}</ref><ref>{{Cite web|url=https://lagosmums.com/lola-ogunnaike-interviews-michelle-obama/|title=Lola Ogunnaike Interviews Michelle Obama|date=2011-08-28|website=Lagosmums|language=en-GB|access-date=2020-05-09}}</ref><ref>{{Cite web|url=https://trueafrica.co/article/lola-ogunnaike-the-reporter-who-interviewed-michelle-obama-talks-african-media/|title=TRUE Africa {{!}} Lola Ogunnaike: the reporter, who interviewed Michelle Obama, talks President Buhari|date=2015-10-05|website=TRUE Africa|language=en|access-date=2020-05-09}}</ref><ref>{{Cite web|url=http://goldenicons.com/lola-o-hosts-michelle-obama/|title=BET Journalist, Lola Ogunnaike, accompanied First Lady Michelle Obama during her recent trip to South Africa and Botswana|last=goldenicons|date=2011-08-25|website=Golden Icons|language=en-US|access-date=2020-05-09}}{{Pranala mati|date=Mei 2021 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> Lola juga seorang reporter di New York Daily News, di mana ia meliput berita tentang selebriti dan hiburan untuk "''NOW''," bagian hiburan surat kabar, dan untuk kolom Rush dan Molloy.<ref>{{Cite web|url=https://www.nydailynews.com/snyde/ny-coronavirus-naomi-campbell-photographer-model-essence-50th-20200506-kfsx5ylcqnhkjklwids52y54pq-story.html|title=Supermodel Naomi Campbell is photographer and cover subject for Essence magazine’s 50th anniversary issue|last=Daniels|first=Karu F.|website=nydailynews.com|access-date=2020-05-09}}</ref><ref>{{Cite web|url=https://www.nydailynews.com/letting-sunshine-mellowest-rapper-missy-elliott-ball-fire-article-1.903901|title=LETTING THE SUNSHINE IN At her mellowest, rapper Missy Elliott is still a ball of fire|last=Ogunnaike|first=Lola|website=nydailynews.com|access-date=2020-05-09}}</ref> Ia adalah mantan koresponden di "American Morning" CNN.<ref>{{Cite book|url=http://archive.org/details/bestmusicwriting00carr|title=Best music writing 2010|last=Carr|first=Daphne|last2=Powers|first2=Ann|date=2010|publisher=Cambridge, MA : Da Capo|others=The Archive of Contemporary Music}}</ref><ref>{{Cite book|url=https://books.google.co.id/books?id=BN8iAQAAMAAJ&q=lola+ogunnaike+at+new+york+times&dq=lola+ogunnaike+at+new+york+times&redir_esc=y|title=Who's Who in Black New York City: The Inaugural Edition|last=Media|first=Inc Real Times|date=2009|publisher=Whos Who Publishing Company|isbn=978-1-933879-55-0|language=en}}</ref><ref>{{Cite web|url=https://edition.cnn.com/CNN/anchors_reporters/ogunnaike.lola.html|title=CNN Programs - Anchors/Reporters - Lola Ogunnaike|website=edition.cnn.com|access-date=2020-05-09}}</ref>
Dia telah muncul di beberapa program televisi seperti NBC's Today Show, MTV dan VH1. Dia terdaftar pada Mei 2007 sebagai ‘150 Orang Hitam Paling Berpengaruh di Amerika”. Dia saat ini menjadi pembawa acara untuk Arise Entertainment 360.<ref>{{Cite web|url=https://bodyimagemovement.com/arise-entertainment-360/|title=Arise Entertainment 360|date=2015-05-07|website=Body Image Movement|language=en-AU|access-date=2020-05-09}}</ref><ref>{{Cite web|url=https://www.essence.com/news/centric-tv-air-arise-entertainment-360/|title=Centric TV to Air 'Arise Entertainment 360!'|website=Essence|language=en-US|access-date=2020-05-09}}</ref>
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